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László Poppe and
Mihály Nógrádi
Editors

László Poppe, József Nagy, Gábor

Hornyánszky and Zoltán Boros
Contributing Authors

Stereochemistry and Stereoselective

Synthesis
Edited by
László Poppe and Mihály Nógrádi

Contributing Authors
László Poppe, József Nagy, Gábor Hornyánszky and
Zoltán Boros

Stereochemistry and Stereoselective

Synthesis

An Introduction
Editors All books published by Wiley-VCH are
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 V

Contents

About the Companion Website XI

Introduction XIII

Part I Basic Concepts at the Molecular Level 1

1 Structure and Properties 3

1.1 The Covalent Bond and the Octet Rule 3
1.2 Representation of Chemical Structures 6
1.3 Description of Chemical Structure 8
1.4 Problems of Correlating Chemical Structure with Properties 10
References 16

2 Concepts of Stereochemistry 17
2.1 Elements and Groups of Symmetry 17
2.2 Classification of the Basic Concepts of Stereochemistry 21
2.2.1 Concepts Related to a Single Object (Molecule) or Parts of
Thereof 23
2.2.2 Concepts Referring to the Relationship of Two Objects (Molecules)
(Isomerism, Isomeric Relationship) 25
2.2.3 Concepts Referring to the Relationship of Parts of an Object
(Molecule) or Modes of Approach to an Object (Topicity) 31
2.3 Stereodescriptors 37
2.3.1 The D/L System, Fischer’s Projection 39
2.3.2 The R/S System 41
2.3.3 Hindered Rotation around a Double Bond, E/Z Isomerism 43
2.3.4 Axial Chirality, Helicity, M/P Descriptors 44
2.3.5 Planar Chirality, Rp /Sp -Descriptors 46
2.4 Prostereogenic Elements, Prochirality 48
2.4.1 Prostereoisomerism and Prochirality 48
2.4.2 Distinction of Stereoheterotopic Groups, the pro-R/pro-S
Notation 50
2.4.3 Prochiral and meso Compounds, Center of Pseudoasymmetry 52
2.4.4 Distinguishing of Stereoheterotopic Faces, the Re/Si Notation 54
References 56
VI Contents

Problems to Chapters 1 and 2 57

Part II Properties at the Level of Material Assemblies 65

3 Timescale, Conformational Changes 67

3.1 Conformational Motion of Ethane and Its Optical Inactivity 67
3.2 Conformations and Optical Inactivity of n-Butane and
1,2-Dichloroethane 70
3.3 Biphenyl and Substituted Biphenyls, Atropisomerism 71
References 74

4 Absolute Configuration 75
4.1 Methods to Determine Absolute Configuration 78
4.2 Strategies to Determine Absolute Configuration by Chemical
Correlation 79
4.2.1 Transformations of the Ligands Attached to an Asymmetric Unit
without Influencing the Bonds between the Asymmetric Unit and
the Ligands 81
4.2.2 Degradation of Multiple Asymmetric Units of a More Complex
Molecule until Only One Remains Intact 81
4.2.3 Stereoconstructive Strategy That Adds Further Asymmetric Elements
to One of the Known Absolute Configuration without Influencing
the Bonds between Its Asymmetric Unit and Ligands 82
4.2.4 Symmetrization of One or More Asymmetric Units Leading to a
Common Compound with Less (but More Than One) Asymmetric
Elements 82
4.2.5 Transformations Involving Stereospecific Reactions of Known
Stereochemistry Influencing the Bonds between the Asymmetric
Unit and the Ligands 83
References 84

5 Methods for the Determination of Enantiomeric Composition 87

5.1 Chiroptical Methods 89
5.2 NMR Methods Based on Diastereotopicity 89
5.2.1 Methods Based on Forming Diastereomeric Derivatives 89
5.2.2 NMR Methods Based on the Use of Chiral Solvents (Solvating
Agents) 92
5.2.3 NMR Methods Based on Chiral Shift Reagents 93
5.3 Chromatographic and Related Methods Based on Diastereomeric
Interactions 94
5.3.1 Separation on a Diastereoselective (Achiral) Stationary Phase 94
5.3.2 Use of an Enantioselective (Chiral) Stationary Phase 96
5.3.2.1 Gas Chromatography 97
5.3.2.2 High-Performance Liquid Chromatography 98
5.4 Kinetic Methods Based on Enantiomer Selectivity 99
 Contents VII

5.4.1 Enzymatic Methods 100

5.4.2 Nonenzymatic (Chemical) Methods 101
5.5 Fusion Methods 102
5.6 Methods Based on Isotope Dilution 102
5.7 Potentiometric Methods 102
References 103

6 Tautomerism 105
6.1 Types of Tautomerism 106
6.1.1 Valence Tautomerism 106
6.1.2 Classic Tautomerism 107
6.2 Prototropy 108
6.2.1 Oxo–Enol Tautomerism 108
6.2.2 Imine–Enamine Tautomerism 110
6.2.3 Amide–Imido Acid and Related Tautomerisms 112
6.2.4 Tautomerism of Aliphatic Nitro Compounds 113
6.2.5 Tautomerism of Carbonic Acid Derivatives Containing Cumulated
Double Bonds 113
6.2.6 Ring–Chain Tautomerism 114
6.3 Methods for Studying Tautomerism 115
6.4 Nitrogen Inversion 115
References 116

Problems to Part II 117

Part III General Characteristics of Stereoselective Reactions 125

7 Types and Classification of Selectivities 127

7.1 Main Types of Selectivity 127
7.1.1 Substrate Selectivity 127
7.1.2 Product Selectivity 127
7.2 Classification of Selectivities 128
7.2.1 Chemoselectivity 130
7.2.1.1 Interpretation of Chemoselectivity 130
7.2.1.2 Chemoselectivity in Biocatalysis 131
7.2.2 Regioselectivity 131
7.2.2.1 Substrate Regioselectivity 132
7.2.2.2 Product Regioselectivity 132
References 135

8 Stereoselective and Stereospecific Reactions 137

8.1 Stereospecificity 137
8.2 Stereoselectivity 138
8.3 Selective Syntheses of Enantiomers 139
8.4 Diastereomer Selectivity 141
VIII Contents

8.5 Diastereotope Selectivity 142

8.5.1 Diastereotope Selectivity with the Formation of a New Chiral
Element 143
8.5.2 Chiral Auxiliary Groups 145
8.5.3 Enantiodivergent Synthetic Strategy Employing Chiral Auxiliary
Groups 146
8.5.4 Significance of Separating the Diastereomers Formed 147
8.5.4.1 Purification of Enantiomers by the Separation of Diastereomers
Formed with the Aid of an Achiral Bidentate Reagent 149
8.5.5 Diastereotopic Version of Asymmetric Transformation by Induced
Crystallization (CIAT) Involving Diastereotopic Interactions 149
8.5.6 Diastereotope Selectivity in Biotransformations 153
8.5.6.1 Selective Biotransformations of Diastereotopic Groups 153
8.5.6.2 Selective Biotransformation of Diastereotopic Faces 153
8.6 Enantiomer Selectivity 154
8.6.1 Degree of Enantiomer Selectivity in Irreversible Processes 155
8.6.2 Kinetic Resolution Using Chemical Systems 158
8.6.2.1 Parallel Kinetic Resolution with Chemical Systems 160
8.6.3 Kinetic Resolution with Biocatalysts 160
8.6.3.1 Parallel Kinetic Resolution with Biocatalysis 166
8.6.4 Dynamic Kinetic Resolution (DKR) 166
8.6.4.1 Dynamic Kinetic Resolution Using Chemical Systems 167
8.6.4.2 Dynamic Kinetic Resolutions with Biocatalysis 168
8.6.4.3 Dynamic Kinetic Resolution (DKR) Involving Base-Catalyzed
Racemization 168
8.6.4.4 DKR Involving Acid-Catalyzed Racemization 169
8.6.4.5 DKR Combined with Racemization by Ring Opening 169
8.6.4.6 DKR Involving Metal-Catalyzed Racemization 170
8.6.4.7 Dynamic Kinetic Resolutions Utilizing Other Chemical
Racemization Processes 171
8.6.4.8 Dynamic Kinetic Resolution Comprising Biocatalytic
Racemization 171
8.6.5 Crystallization-Induced Dynamic Resolution (CIDR) 172
8.6.6 Kinetic Resolution Followed by Configurational Inversion 174
8.7 Enantiotope Selectivity 175
8.7.1 Enantiotope Selectivity in Chemical Systems 177
8.7.2 Enantiotope Selectivity in Biocatalytic Systems 179
8.7.2.1 Transformations of Enantiotopic Groups by Biocatalysis 179
8.7.3 Consequences of Opposing Enantiotope-Selective
Transformations 182
8.7.4 Kinetic Amplification 183
8.7.5 Enantiodivergent Reactions Following the Transformation of
Enantiotopic Groups 185
8.8 Combination of More Than One Type of Selectivity 186
References 187
 Contents IX

Problems to Part III 189

Part IV Applications of Enantioselective Methods 201

9 Stoichiometric Methods of Enantioselective Synthesis 203

9.1 Diastereotope Selective Methods 203
9.1.1 Substrate-Controlled Selectivity 203
9.1.2 Diastereotope Selectivity Controlled by an Auxiliary
Group–Enantioselective Synthesis 204
9.1.3 Double Asymmetric Induction. Concerted Diastereotope Selectivity
of Chiral Molecules 208
9.2 Enantiotope Selective Methods 211
9.2.1 Reagent-Controlled Selectivity 211

10 Catalytic Methods of Enantioselective Synthesis 213

10.1 Chemical Catalysis 213
10.1.1 Chiral (Asymmetric) Catalytic Hydrogenation 213
10.1.2 Enantiotope-Selective Catalytic Epoxidation 219
10.1.3 Stereoselective Catalytic Diol Formation 228
10.1.4 Formation of a C–C Bond by Chiral Catalysis 229
10.1.5 Stereoselective Catalytic Michael Additions 232
10.1.6 Catalytic Stereoselective Nucleophilic Addition Onto a Carbonyl
Group 234
10.1.7 Double-Enantiotope-Selective Catalytic Aldol Reactions 238
10.1.8 Enantiotope-Selective Catalytic Simmons–Smith Reaction
(Cyclopropanation) 239
10.1.9 Stereoselective Catalytic Diels–Alder Reaction 240
10.2 Biocatalysis 244
10.2.1 Substrate Selectivity (Enantiomer Selectivity)–Kinetic
Resolution 246
10.2.2 Substrate Selectivity (Enantiomer Selectivity)–Dynamic Kinetic
Resolution 249
10.2.3 Enantiotope-Selective Biotransformations 251
10.2.3.1 Oxidoreductases 251
10.2.3.2 Lyases 253

Index 257
 XI

About the Companion Website

This book is accompanied by a companion website:

www.wiley.com/go/poppe/stereochemistry

The website includes animations about the software developer.

 XIII

Introduction

Nowadays, the development of molecular sciences brings about a revolutionary

change of our world, life, and culture as once did the industrial revolution laying
the foundations of our modern world. This molecular revolution, one of the mile-
stones of which was the elucidation of the structure of the hitherto largest known
natural compound, the human genome, extends in a dimension hitherto unheard
of our knowledge of both ourselves and the universe. A key element of this molec-
ular revolution is chemistry, and within it organic chemistry, contributing a lion’s
share in the twentieth and twenty-first centuries to the significant achievements
of biology, medical, material, and environment sciences.
Similar to other sciences, organic chemistry plays a key role in our knowledge of
the universe, and within chemistry a special place is allotted to the study of organic
molecules. Apart from the potential of synthetic organic chemistry to construct
molecules to be found in nature, it is capable to construct molecules not produced
in nature.
A key problem of organic synthesis is selectivity, and within this domain
stereoselectivity, a capacity to prepare selectively just one of the possible
stereoisomeric structures. The importance of stereochemistry has been recog-
nized in the very early period of organic chemistry: J. B. Biot observed in 1815
that certain organic compounds and their solutions rotate the plane of planar
polarized light. L. Pasteur (1948) separated (resolved) the optically inactive
tartaric acid to two optically active forms and made one of the most important
hypotheses in stereochemistry, namely that the two forms are related as mirror
images. J. A. LeBel and J. J. van’t Hoff (1874) recognized the tetrahedral bond
structure of carbon and that this structure enables, in the case of four different
ligands, the existence of two nonidentical mirror image structures (enantiomers).
H. E. Fischer after having identified and synthesized most of the 16 possible
stereoisomeric forms of aldohexoses (1891) suggested a representation of three-
dimensional structures in two dimensions, while M. A. Rosanoff (1905) proposed
the conventional absolute configuration of D-(+)-glyceraldehyde.
Stereochemistry and stereoselective synthesis received a significant impetus in
the middle of the past century when J. M. Bijvoet (1951) determined the actual
absolute configuration of (+)-tartaric sodium rubidium salt with the aid of anoma-
lous scattering in X-ray diffraction.
XIV Introduction

The relevance of stereochemical studies was recognized by awarding a series

of Nobel Prizes. The foundation of modern stereochemistry was laid down in
the monograph of M. S. Newman (1956). D. H. R. Barton and O. Hassel were
awarded the Nobel Prize (1969) for conformational studies, while V. Prelog and
J. W. Cornforth (1975) for analyzing the stereochemistry of enzyme-catalyzed
reactions. Nobel-Prize-winning studies were carried out by D. J. Cram, J. M. Lehn,
and C. J. Pedersen (1987) of selective interactions in supramolecular systems;
W. S. Knowles, R. Noyori, and B. Sharpless (2001) for elaborating stereoselective
synthetic methods.
The practical importance of stereochemistry is accentuated by the fact that
nowadays almost exclusively enantiopure drugs can be registered and the inactive
enantiomers are regarded as “contaminants.” It is therefore not surprising
that manufacturing enantiopure compounds is a multibillion dollar business
increasing about 10% per year. Accordingly, development of stereoselective
methodology of manufacturing and analyzing pure enantiomers is becoming a
central issue for the pharmaceutical, pesticide, cosmetic, and even of household
chemical industry.
To write a textbook on any field of science is always challenging, especially about
stereochemistry and stereoselective methodology, which is now in extremely
fast development. The present work is intended to serve not only students of
chemistry but also a wider circle of readers, namely to those whose main interest
is outside stereochemistry or even organic chemistry, but who wish to have an
overview about the problems, the scope, and potentials of this highly interesting
field of chemistry. We hope to find among our potential readers biochemists,
polymer chemists, pharmacologists, pharmacists, biologists, and workers in
other branches of biosciences.
 1

Part I
Basic Concepts at the Molecular Level

The inherent difficulty of correlating structure with properties is that structure

is a concept at the molecular (microscopic) level, while properties are in general
“macroscopic” manifestations. Difficulties of comparing the two levels can be
attributed to two factors: the quantity of material and the time required for the
determination of properties.
This part deals with the basic concepts of stereochemistry focusing at the molec-
ular (microscopic) level.

Stereochemistry and Stereoselective Synthesis: An Introduction, First Edition.

László Poppe and Mihály Nógrádi.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2016 by Wiley-VCH Verlag GmbH & Co. KGaA.
Companion Website: www.wiley.com/go/poppe/stereochemistry
 3

1
Structure and Properties

A general opinion of chemists adopted by textbooks is that in chemistry,

structure1) is a central concept: the key to everything. Properties2) of a given
substance depend on the number and nature of its constituting atoms and their
mode of connection (connectedness). It is less obvious but quite important that
looking at structural formula, a well-versed chemist should be able to deduce
many properties of a substance. In order to exploit this possibility, in this chapter,
we are going to define some basic principles associated with structure and
properties. After having defined the concept of structure, we will proceed to
discuss correlations of structure and properties, with special emphasis on the
spatial features of structure and properties derived from changes thereof. First of
all, we will discuss properties derived from the spatial structure of typical organic
compounds; but for the sake of completeness, the stereochemical features of
inorganic compounds will be dealt briefly as well.

1.1
The Covalent Bond and the Octet Rule

The covalent nature of the chemical bond, assuming a shared pair of electrons, was
first proposed by G. N. Lewis in 1916 [1]. According to this concept, by sharing
two electrons, two hydrogen atoms can establish a stable bond by forming a closed
shell of electrons similar to that of the noble gas helium (Figure 1.1).
In the Lewis structures, electrons are symbolized by dots. The amount of
energy required to dissociate a hydrogen molecule to two hydrogen atoms is
called the bond dissociation (or bond) energy. In the case of H2 , this is quite high:
435 kJ mol−1 .

1) Under structure, chemists often understand a single state of a single molecule; therefore, at this
level, structure is a microscopic concept (to be discussed in more detail later).
2) Properties of a material are generally defined not on the basis of a given state of a single molecular
structure but on an assembly of a large number of molecules, on a timescale relatively long com-
pared to the timescale of molecular events, and therefore these properties are generally macroscopic
concepts.

Stereochemistry and Stereoselective Synthesis: An Introduction, First Edition.

László Poppe and Mihály Nógrádi.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2016 by Wiley-VCH Verlag GmbH & Co. KGaA.
Companion Website: www.wiley.com/go/poppe/stereochemistry
4 1 Structure and Properties

H• •H H:H

Two hydrogen atoms: Hydrogen molecule:

open electron shells with one electron with one pair of shared electrons

Figure 1.1 Formation of the covalent bond of the hydrogen molecule.

2 H H H Hydrogen molecule HH

2 F F F Fluorine molecule FF

H
H
4 H + C H C H Methane molecule HC H
H
H

2 O + C O C O Carbon dioxide O C O
molecule

Figure 1.2 Covalent bonds in some simple molecules (Lewis representation).

While with hydrogen molecule the number of electrons present in the valence
forming shell is limited to two, in the Lewis model, molecules composed from ele-
ments of the second row (Li, Be, B, C, N. O, F, and Ne) in the valence shells contain
eight (shared and unshared) electrons. Most organic compounds follow the octet
rule: on formation of their compounds, electrons are taken up, and elements are
shared or removed in a way that they should assume a stable structure involv-
ing eight valence electrons. When in compounds of carbon, nitrogen, oxygen, and
fluorine, the octet rule is valid, their electron configuration is analogous to that of
the noble gas neon. Lewis representation of some simple molecules is shown in
Figure 1.2.
Such structures showing the distribution of electrons (Lewis structures) are use-
ful aids for understanding covalent bond formation, but it is simpler to use the
s.c. Kekulé formulas.3) The latter are derived from Lewis formulas by replac-
ing a shared pair of electrons with a line connecting the corresponding atomic
symbols. Nonbonding electrons are shown by dots. Examples for structural for-
mulas drawn according to this principle are shown in Table 1.1. As a further

3) Based on the work of A. M. Butlerov, A. Couper, and F. A. Kekulé but at variance with their original
formulas, bonds between elements are shown by lines (Kekulé formulas).
 1.1 The Covalent Bond and the Octet Rule 5

Table 1.1 Lewis and Kekulé formulas of some simple molecules.

Name Molecular Lewis formula Kekulé formula

formula

Water H2O HO H O
H H

Ammonia H3N HNH H N H

H H

H H
Methane CH4 HCH H C H
H H

H H
Methanol CH4O HCOH H C O H
H H

HH H H
Methylamine CH5N HCN H C N H
H H

H H H H
Ethene C2H4 C C C C
H H H H

H H
Formaldehyde CH2O C O C O
H H

Acetylene C2H2 HC CH H C C H

Hydrogen cyanide CHN HN C H C N

simplification of Kekulé formulas, nonbonding electrons are not shown since these
can be readily calculated following the octet rule.
As illustrated in Table 1.1 by ethene, formaldehyde, acetylene, and hydrogen
cyanide, atoms may share more than one pair of electrons forming in this way
multiple bonds. Compounds of boron, such as BH3 or BF3 , are exceptional in
a way that the valence shell of boron is not filled up with electrons as would be
required by the octet rule. Accordingly, these compounds have a high affinity to
electrons and are very reactive.
Valence is the number of those valence electrons, which must be taken up or
shed that the valence shell should attain the octet state (Table 1.2). In their covalent
compounds, the number of bonds adjoined to an atom is equal to the valence of
the given atom. Valences listed in Table 1.2 are typical of atoms common in organic
compounds.
6 1 Structure and Properties

Table 1.2 Valence states of selected elements common in organic compounds.

Atom H C N O F Cl Br I

Valence 1 4 3 2 1 1 1 1

1.2
Representation of Chemical Structures

For the representation of simpler compounds, condensed Kekulé formulas are

suitable; but this is a cumbersome way to represent more complex compounds.
Thus, cyclic compounds are best represented by further simplified, s.c. linear for-
mulas. Application of linear formulas is exemplified by formulas for cycloalkanes
(Figure 1.3).
Linear formulas are also convenient to depict open chain compounds
(Figure 1.4).

H2
H2
H2 C
H2C CH2 C
H2 C H2C CH2
C H2C CH2 H2C CH2 H2C CH2 H2C CH2
C
H2C CH2 H2C CH2 H2C CH2 H2 H2C CH2

Cyclopropane Cyclobutane Cyclopentane Cylohexane Cycloheptane

Figure 1.3 Representation of cycloalkanes by linear formulas.

OH
OH
OH
Butane 1-Butene 1-Butyne 1-Butanol 2-Butanol tert-Butanol

Cl
O O
NH2 O Cl
OH
2-Butanone Allylamine Diethyl ether 6-Chloromethyl-2,3-dimethyl- Chloroacetic
nonane acid

OH O H
N N
N O O N
Acetone oxime N,N-Dimethyl- Vinyl acetate Acetonitrile N-Ethylisopropylamine
formamide

Figure 1.4 Representation of open-chain compounds with linear formulas.

 1.2 Representation of Chemical Structures 7

H H H
Methanol CH3OH H C O H OH H
H OH

H
H C H
C C _
Pyridine C5H5N
C C
H N H N

Escitalopram _ _ _ N

Figure 1.5 Various modes of representation for methanol, pyridine, and the antidepressant
escitalopram.

When drawing linear formulas, for simplicity, symbols of carbon atoms, the
pairs of electrons, and hydrogen atoms attached to carbons are omitted. Accord-
ingly, all end points, breaking points, and points of branching represent a carbon
atom. Multiple bonds are shown by an appropriate number of parallel lines. Heavy
atoms other than carbon are shown by their atomic symbols together with the
hydrogen atoms attached.
Additional ways of representation are shown in Figure 1.5 by the example of
methanol, pyridine, and the antidepressant escitalopram. Representations include
the following:

A: Name (trivial or systematic)

B: Condensed formulas (generally suitable for printing in a single line)
C: Kekulé formulas (showing all the atoms and bonds)
D: Linear formulas (hydrogens omitted, breaking, branching, and end points
represent carbon atoms; heavy atoms are shown with the hydrogen attached)
E: Stereoformulas4) (depicting the spatial orientation of bonds)
F: Ball and stick model (often used to depict X-ray structures or computed
models)
G: Space-filling model (approaches the electron distribution).

Figure 1.5 well demonstrates that for smaller open-chain organic compounds
(e.g., methanol), it is the condensed or Kekulé formula that is the most appro-
priate for the demonstration of the two-dimensional features of the structure. In
case of smaller cyclic compounds (e.g., pyridine), the linear formulas are most
often used. To depict more complex structures (e.g., escitalopram), condensed

4) The details of the use of stereo formulas are exactly defined by IUPAC recommendations [2]. Easily
perceptible stereo formulas have only become generally used in the second half of the twentieth
century. Earlier, various other representations were used.
8 1 Structure and Properties

or Kekulé representations are practically useless, and therefore a combination of

linear and stereo representation is recommended. The complete stereostructure
of molecules can be best depicted by a simplified representation of 3D structures.
In Figure 1.5, two possible modes of representation of molecular models that is,
ball and stick and space-filling models are shown.5) As can be seen with more com-
plex molecules, space-filling models refer to their overall shape, while the details
of the structure are less apparent.

1.3
Description of Chemical Structure

Chapters of the rules of International Union of Pure and Applied Chemistry

(IUPAC) for naming compounds [3] do not give a precise definition of what
should be understood under “chemical structure.” Therefore, we define in a
general way as chemical structure as it is understood by crystallographers:
chemical structure is an accurate description of the spatial arrangement of the
constituting atoms (atomic nuclei) in space.
The exact spatial arrangement of atoms can be described, for instance, by their
Cartesian coordinates.6) From a structural point of view, however, it is not the
absolute position and orientation of the molecule that is decisive; therefore, it is
often more useful to describe the relative position of atoms by s.c. internal coor-
dinates7) (Figure 1.6). Internal coordinates for the description of molecules are
the bond lengths (r), the bond angles (𝛼), and the torsion angles (𝜔).8)
For the description of molecules containing two atoms (I), besides defining the
type of atoms (A, B), it is sufficient to give the bond length as a single internal
coordinate. In organic molecules, the value of bond lengths varies in a relatively
narrow range (Table 1.3).
The structure of a triatomic molecule (II) is characterized by the type of atoms
(A, B, and C), two bond lengths (r1 and r2 ), and one bond angle (𝛼).9) In real
triatomic molecules, bond lengths and bond angles depend on the type of consti-
tuting atoms, their hybridization state, and the order of the bonds (Figure 1.7).
It is apparent from Figure 1.7 that in triatomic molecules, bond angles vary
in a wide range. The molecules of hydrogen sulfide and water form an angular

5) Computer programs suitable to visualize chemical structures offer further possibilities (e.g., wire
models, ball and stick models, covering surfaces according to various properties and combinations
thereof ).
6) A molecule containing n atoms can have a maximum of 3n − 6 internal degrees of freedom and can
be described by 3n − 6 Cartesian coordinates. Use of Cartesian coordinates also defines its absolute
position, and therefore their use is uncomfortable.
7) A molecule containing n atoms can have a maximum of 3n − 6 internal degrees of freedom and
can be described by 3n − 6 internal coordinates. Internal coordinates reflect to local bonds and
symmetries; they can be composed by linear combinations of Cartesian coordinates.
8) Bond angles are often denoted by the symbol Θ. In polymer chemistry, it is usual to denote bond
angles as 𝜏, while the symbol Θ is for torsion angles.
9) Bond angles are sometimes called valence angles.
 1.3 Description of Chemical Structure 9

D
r3
α2 α3
B ω 2 D B ω r2
r1 r2 α r1
B B r1
r r3
A B A α C A r1 α1
r2 C A α1 r2 C A α1 C
α2
r
II α1 + α2 + α2 = 180° ω = 180° ω = 0° D
3
I
III IVa IVs

D D
r3 r3
B ω B ω
α2 α3 α2 α3 r1 α2 α2
D r1 D
B B r3 r3
A α1 r2 C A α1 r2 C
A r1 α1
r2 C A r1 α1
r2 C
α1+α2+α2 < 180° α1+α2+α2 < 180° ω = 120° ω = −120°
IIIR IIIS IV+g IV–g
D D
C B A B B A
B C
A A D D

Figure 1.6 Characterization of molecules consisting of two, three, and four atoms with inter-
nal coordinates.

Table 1.3 Characteristic values of bond lengths commonly occurring in organic

compounds.

C–C C==C C≡C C–H C–O C==O C–N C–S C–F C–Cl C–Br C–I

pm 154 133 120 109 143 122 147 182 135 176 192 212
Å 1.54 1.33 1.20 1.09 1.43 1.22 1.47 1.82 1.35 1.76 1.92 2.12

S O O C O H C N
H H H H
α = 92.1° α = 103.9° α = 180° α = 180°
Hydrogen sulfide Water Carbon dioxide Hydrogen cyanide

Figure 1.7 Bond angles in selected triatomic molecules.

structure owing to the presence of two nonbonding pairs of electrons in an

approximately tetrahedral arrangement. (The difference in the bond angles is
caused by the different strengths of repulsion between the pairs of electrons.) On
the other hand, hydrogen cyanide and carbon dioxide are linear due to the sp
hybridization state of the central atom. In bond angles between atoms of given
types, the value of bond angles varies in a narrow range and therefore when
discussing structures, organic chemists take them as constant.
Molecules consisting of four atoms (A, B, C, and D) present a new situation
(Figure 1.6). If the fourth atom (D) is attached to the central atom (B) of the chain
formed by the other three, we are dealing with a branched structure (Figure 1.6,
III, IIIR , and IIIS ). When the four atoms (A, B, C, and D) are coplanar (the sum of
Exploring the Variety of Random
Documents with Different Content
while fighting beside the French in France, she still had troops
sufficient to attack the enemy elsewhere. Even as those gallant
Indian and British troops with the Mesopotamia Force charged down
upon the trenches at Shaiba, other British troops—men from
England, from Australia, and New Zealand—were gathering in the
neighbourhood of Egypt. Indeed, within a few days there occurred a
landing on the Peninsula of Gallipoli, a most desperate and gallant
undertaking, which launched Great Britain and France into a conflict
the difficulty of which was stupendous, and the result of which
cannot be said to have been altogether a failure, though it failed to
gain for us the capture of those forts which line the approach to
Constantinople. A conflict, in fact, abortive, as it proved, yet one
which struck the Turks an exceedingly heavy blow, and set up a
record of bravery and determination on the part of British and
French which will never be exceeded.
Was there ever such an expedition as that which set out for
Nasiriyeh?
"Queer, ain't it?" remarked Philip, on the point of embarking with his
chum Geoff on board the steam-launch which they had captured
from the enemy in the midst of the same marshes whither they were
now bound. "Did you ever see such a collection of boats and
fellows? and the navy look as though they meant to make a race of
the business."
There was a string of bellums—the shallow light craft common to
that part of Mesopotamia, and used by the natives for progress
through the marshes—towing at the tail end of the steam-launch—
bellums crammed with British soldiers and with Indians. There were
motor-boats near at hand, pushing their busy way across the Shatt-
el-Arab; there were shallow-draft steamers brought from India,
cranky, dilapidated, rusty vessels, which looked as though they had
done long service, and had arrived at a time when they were fit for
the scrap-heap only, or to be relegated to long and continuous rest.
As a matter of fact, many of these curious craft—long since
abandoned as useless by their owners—had been brought across
from India, surviving in a most extraordinary manner a voyage which
might have been expected to smash them to pieces, and to shake
their already quivering sides so severely that if they had been
swamped, if the ocean had poured through many a crevice, it would
have been a wonder to no one. And there they were, at anchor in
the river, their decks packed with men of the navy—men in duck
white or in khaki, grinning fellows, who shouted to their comrades of
the army.
"Cheer oh, navy'll be in first!" they bellowed. "We're in for the
Turkish stakes, and back ourselves to beat the army."
What a scene it was when the expedition set off at length! The
lighter craft finding their way through the marshes, and steering an
irregular course amongst the muddy islets, whilst the vessels
drawing deeper water ploughed their way along the uncertain course
of the Euphrates, and stemmed the gentle flood down which Phil
and Geoff had steamed with their Turkish prisoner. Little tails of open
boats trailed at the stern of every steamer, while not a few, manned
by natives, with soldiers aboard them, were paddled into the
marshes farther afield on the outskirts of this huge inundation.
There were other troops wading knee-deep, all with the one
objective—Nasiriyeh and the Turkish camp. Perhaps never before
had such an amazingly curious, amphibious expedition been
undertaken, and it is quite certain that never before had British and
Indian sailors and soldiers enjoyed a thing more hugely.
"A regular sort of mud lark," Phil called out as the launch ran on a
submerged bank of mud, and came to an abrupt halt, causing the
bellum towing nearest to her to collide violently with her stern and
capsize promptly. There were roars of laughter as the men fell into
the water and got to their feet again, dripping, and standing there
with the water hardly higher than their knees, grimacing and shaking
themselves like dogs.
"All overboard!" cried Geoff, who was in command of the launch.
"There's no use in trying to pole her off, for she's hard and fast.
Overboard with you!"
Pulling his long boots off and his breeches higher up his legs, he was
over the side in a twinkling, while the crew, enjoying the experience
amazingly, followed him, Phil helping to set an example.
"Now, all together, boys!" shouted Geoff. "Pull her off! Pull her back!
That's done it; she's moving!"
Not once, but half a dozen times, in the next two or three days,
were they forced to extricate themselves from a similar sort of
situation by similar methods. For, let us explain, there was no
opportunity to take careful account of the obstacles before them, to
steer a slow and cautious course, and to make a complete
reconnaissance of the route they were to follow. Under ordinary
conditions, with time at their disposal, Geoff would have steered his
launch at a placid pace, and would have avoided enclosed waters
where islands of mud abounded; but now, with this expedition, it
was a case of each man for himself, of push ahead all the time. It
was a race, in fact, a friendly race, between the army and the navy,
each service vying with the other in its efforts to push onward, and
each secretly determined to get to the goal before the other.
"If we don't look out we shall be running our heads into a hornets'
nest," Geoff cried irritably, when, for the fifth time at least, he and
his crew had had to leap into the shallow water and pull their vessel
free of a mud-bank. "This sort of headlong course will not help us to
beat the enemy, but will give them an enormous opportunity."
Whereat Phil grinned. He was one of those incautious, careless,
happy-go-lucky sort of subalterns who never think of consequences,
and who, perhaps for that very reason, so seldom come to grief.
Perhaps it was a lucky star which always watched over Phil's
progress, for, in any case, happy-go-lucky though he was, careless to
an irritating degree, he yet had so far come through many a little
adventure unscathed.
"Tremendous opportunity—yes!" he told Geoff. "But—but will they
take it? Bet you they're already thinking of bolting; for don't forget,
my boy, we've given them a pretty hard hammering. Besides, an
expedition such as this is, spread out through the marshes, ain't so
jolly easy to tackle. You could stop a portion, perhaps—say one
flank, or the portion in the centre of the ground, or rather the water.
What do you Head-quarters chaps call it? It would be called terrain if
it was a question of land operations, and I don't happen to know the
term under these conditions. But that's what might happen; one
portion of our spread-out front might get stopped, but the others
would push on like blazes! Cheer up, Geoff! It'll all come right, and
you'll earn promotion yet."
It always ended like that with such a fellow as Phil, and Geoff,
cautious and earnest young officer though he was, was forced to
laugh uproariously, and join in Phil's merriment. And, after all, if
caution had been thrown to the winds by all of them—which was far
from being the case—caution on his part would hardly remedy the
situation. Pushing on, therefore, and taking the most out of his
steam-launch, thrashing her across every open strip of water till her
bow waves washed almost aboard, and until the rope to which the
bellums were attached was drawn like a bow-string, and the
unfortunate individuals aboard those craft drenched with spray, he
wriggled his way forward with other boats of the expedition,
determined to be well in the van at the coming conflict. Then, as the
dusk fell, and the boats tied up or anchored for the night, he
selected a likely spot towards the edge of the marshes, and dropped
anchor. Entering a bellum, he went off towards one of the bigger
craft, aboard which the Staff conducting this extraordinary
expedition were quartered.
"What's up?" asked Philip on his return, the inevitable question that
young officer fired at his comrade. "Of course, everyone knows that
we're jolly near this Nasiriyeh, so to-morrow there'll be something
doing, eh?"
"Come over here," Geoff said, nodding towards the stern of the
vessel.
"Secrets, eh?" grinned Philip, yet wonderfully eager to hear what
Geoff had to say. "Now then, what's the business?"
"A forward move to-morrow, as you might expect, but before that a
reconnaissance."
"A re—con—nais—sance! Jingo! Ain't that a mouthful? Put in simpler
language, a sort of scouting expedition," smiled Philip, sucking
furiously at a cigarette.
"Just that; an expedition by a small party to discover the actual site
of the Turkish camp and to hear what they are saying."
"Oh! And—but you don't mean——George! That would be ripping!"
Geoff cooled his ardour most brutally. "What would be?" he asked
curtly enough—coldly, in fact, knowing full well what would be the
result of such action.
And, indeed, in a moment the hitherto eager and impulsive Phil was
reduced to a condition almost of despair, was grumbling, was far less
elated; and then, in the dim light which still existed, he caught just a
glimpse of Geoff's bantering smile, and gripped him by the shoulder.
"So you're pulling my leg, eh? It—it——There's a job for us to do?
Something special?"
"There is for me. I have orders to make my way forward as quickly
as possible, and learn all that I can of the enemy. Of course, if you
cared——"
"Cared!" Phil almost shouted, though Geoff warned him instantly to
subdue his tone. For let us explain that if, during the first stage of
this expedition, the rush and hurry and scurry of the navy and army
had been accompanied by cheery calls, by shouts and laughter, by
whistling and singing for some hours, now, at least, silence had been
enjoined upon every man in the marshes. Orders were given by
signs, men whispered to one another, while not an unnecessary
shout came from the vessels of the expedition.
"You'll call the enemy down on us," said Geoff severely. "Of course
you'll come. Everyone knows that, I more than anyone. We'll take
Esbul with us to paddle the bellum, and with a little luck and a little
care I think we shall be able to discover something. You see, Phil,
we have, as it were, a better chance than the other fellows, for
we've been in these marshes before, and know quite a heap about
them."
Standing aboard the steam-launch, now that darkness had settled
down over the River Euphrates and the stagnant marshes stretched
out to the south of it, one would have found it difficult indeed, on
this particular night, to imagine that there were other inhabitants of
this inundated area. Broken up as the surface of the water was, by
innumerable muddy islands, by heaped-up patches of sand, and by
banks of reeds, it was difficult enough even in the daytime to catch
a full view of any other vessel, and now that the night had fallen and
hidden the ships entirely not one was to be seen, though here and
there, in fifty odd places, perhaps, the ruddy glow of pipes could be
seen as the men smoked tranquilly. A gentle hum rose, too, above
the water and the islets—the hum of voices of men of the
expedition, men who talked in undertones, who giggled and laughed
and joked only just above a whisper, and who, eager for the success
of the morrow and for the defeat of the enemy, implicitly obeyed the
orders which had been issued.
Geoff stripped off his service-coat and put his belt round his
shoulder, thus raising his revolver well above the water. Pulling off
his long boots, he donned a pair of tennis shoes—the only change
he had from the heavy pair he wore during the daytime—then,
followed by Phil, he stepped into a bellum, which had been drawn
alongside the steam-launch, and, pushing away from her, at once
felt the thrust of Esbul's paddle.
"Directly ahead!" he told the Armenian; "and don't stop unless we
are brought up by a mud-bank, or unless I snap my fingers."
It was uncannily still all round them, once they had got some two
hundred yards from the somewhat irregular position taken up by the
expeditionary vessels, and banks of reeds and columns of mist
seemed to spring up out of the darkness at them, to hover round
them, and to settle right over them in the most ghostly and
inexplicable manner. Once Geoff snapped his fingers with
unexpected suddenness, and gripped Phil by the wrist to enjoin
silence upon him.
"Eh?" asked that young officer rather breathlessly a few moments
later.
"Thought I saw something," said Geoff.
"So did I. I thought I saw somebody or something half an hour ago.
I've thought it every moment since we left the steam-launch. Bogies,
Geoff?"
"Not nerves, I hope!" came the cheerful answer. "But it's rather
uncanny work, ain't it? I could have sworn just now that a fellow
stood on the edge of an island into which we were running, and I
snapped my fingers; but the way of the boat carried us right on to
the very point where he was standing, and right over it. He had
gone though."
"Like a nasty nightmare!" said Phil. "Let's go ahead; it's cold and
chilly here, and takes the courage out of a fellow."
It was perhaps an hour later, when they had slowly crept forward
towards the Turkish position, and when they had caught sight of a
glow in the distance—the glow of camp-fires—over the position
occupied by the enemy, that the bellum suddenly came to an abrupt
halt, grinding noisily upon the edge of the desert.
"Hard ground," said Geoff. "Looks as though we'd come to the edge
of the marsh land, and—and—I've thought it for some while, the sky
over there shows the reflection from camp-fires. We're near them,
Phil."
"Then let's get nearer. But how are we to find this bellum again,
supposing we leave it?"
That set them cogitating for a few moments while they stepped
ashore, followed by Esbul, and, lifting the bellum clear of the water,
carried her into a bank of reeds which could be heard rustling beside
them.
"How to find her, that's it!" said Geoff, while the respectful Esbul
listened.
"My master," he said of a sudden, for thanks to Major Douglas's
tuition the man could speak English tolerably well. "My master,
perhaps were we to return from the Turkish camp before the dawn
breaks these reeds would aid us. There may be other banks; but, on
the other hand, there may be no more, and thus we should be
aided."
"In any case we've got to chance it," said Geoff lightly. "Now, come
along, and let's make direct for the glow of those camp-fires."
Stealing away from the place where they had hidden their boat, the
three crept cautiously but swiftly towards the enemy's position, and,
ascending slowly as they went, soon gained a ridge, from which they
were able to look right down into the camp where the Turkish
soldiers were concentrated. Lying flat on their faces, they were
busily engaged in taking full stock of what they saw, when a sudden
exclamation came from Esbul.
"Excellency, something behind us!" he whispered.
"Stop! There's someone coming up from the Turkish camp,"
muttered Philip, making a dive for his revolver.
Glancing swiftly in both directions, Geoff was on the point of leading
his comrades to one side, so as to escape the danger of discovery
which seemed to threaten them, when shouts resounded all about
them, and in a trice figures dashed up from every direction,
surrounding the three, and throwing themselves upon Geoff and his
friends with a swiftness that was dramatic.
 CHAPTER XIV
Captured by the Enemy
It was with a shout of astonishment that Geoff realized that he and
Philip and Esbul were discovered. Giving a loud shout of warning, he
flung himself against a figure bounding towards him, and, having no
time to seize his revolver, struck out wildly in the darkness, and the
blow he gave, delivered with all the force of which he was capable,
meeting with no greater resistance than the air, for it shot past the
ear of the individual at whom it was aimed, caused him to lose his
balance and to topple over.
"Ha! Infidel dog!"
The man was down upon him in a moment, and, seizing Geoff's
throat, pinned him to the ground, while, within an instant almost,
our hero felt the prick of the sharp-pointed dagger with which the
man threatened to transfix him. The sudden pain it caused sent a
sickly chill all over his body, and then stimulated him to action.
"Get off!" he roared, and, jerking himself over, swiftly had the man
beneath him. Then, holding the arm which wielded the weapon, he
dealt the man a furious blow between the eyes, and, shaking himself
free, leapt to the assistance of Philip.
"Coming!" he shouted, hearing his chum gasp and seeing his figure
indistinctly in the darkness. And then he went down again, for one
of the band of Turks who had crept so silently towards the three
figures watching their camp, leapt upon his shoulders and bore him,
nose down, to the sand.
"Infidel dog!" he heard again hissed into his ear. "Move, and I strike
life out of you. Move, utter a word, and I slit your throat from ear to
ear."
It was not very pleasant; indeed, a sharp stab of pain in the region
of his shoulder-blade sent another chill down Geoff's spine, and,
together with the increased weight which now held him so firmly to
the sand, helped to discourage further efforts. He was cornered, he
knew; common sense told him that there were many of the enemy
about, that quite half a dozen of them were already seated upon his
body, his legs, and his arms, that further resistance was useless, was
madness in fact, and could end in only one way—in sudden death
for himself and Philip and Esbul.
"Right!" he gasped, spluttering and blowing the sand out of his
mouth. "We surrender!"
"Ah! the dog speaks Turkish, eh! Pull him to his feet; let us see him."
It was another voice that spoke, the voice of a Turkish officer, and at
once those six lusty individuals who had thrown themselves on
Geoff, and who had almost squeezed the life out of him, jerked him
to his feet and held him in an erect position. Had they not done so,
indeed, he would have stumbled and fallen, for, though the contest
had been but a short one, the struggle, whilst it lasted, had been
terrific: the efforts he had made to throw off those men, his kicks
and plunges, and the blows he had endeavoured to aim had taken it
out of Geoff in the most startling manner. He was gasping for breath
now, sweat was pouring from his face, whilst his knees shook and
refused to support him.
"So, infidel dog, you are one of the British who have dared to invade
our country!"
A dusky figure seemed to rise up in front of Geoff, and, approaching
quite close to him, thrust a heavily-moustached face close to his and
peered at him in the darkness. So close indeed was the man that his
breath blew on Geoff's face, and, acting as a tonic as it were, almost
stimulated him to further action. But again discretion, common
sense, told him that to renew the struggle would be futile. "Better
wait till another time," he told himself, gasping in the face of the
Turkish officer—spluttering, indeed, for still sand remained in his
mouth, whilst his nostrils were tickled with the same material.
"Better wait for a while and try our chances in a different manner.
There's Philip!"
Men were approaching from a point but a few feet away, their
figures standing out against the reflection of the camp-fires dotting
the Turkish position, and in amongst them was Geoff's chum, held
firmly by the arms, his head pushed forward by a brawny individual
who gripped the nape of his neck, and his legs already encumbered
by a rope which had been passed loosely round them.
"So, a British officer. Ah!"
"A British officer. Yes!" Geoff admitted between his gasps.
"And one who speaks Turkish, eh?" the man who accosted him
demanded.
"That is so."
"Then how?" asked the Turkish officer. "Where did you learn to
speak our tongue? You are British, you say, and few there are of that
nation who speak our language. Then how? Where? When did you
learn it?"
"One moment; let me sit down for a while," said Geoff, panting so
heavily that he could hardly make the request. "In a little while I will
answer any reasonable question that you may put before me, and in
the meantime you need have little fear; for see, there are perhaps
twenty or thirty men here to support you."
A grim, harsh chuckle came from the Turkish officer, and yet a laugh
which was not altogether disagreeable. If he had been a German
officer, no doubt he would have stormed and raved, and might even
have suggested shooting his prisoners on the spot, so as to get rid
of them; but, being a Turk—and Turkish soldiers, whether they be
officers or fighting-men, have ever proved themselves to be
possessed of gentlemanly feelings—and being moreover satisfied
that the three prisoners he had captured were completely in his
hands, this Turk was by no means ill-pleased, was, in fact, in quite a
genial humour, and, if the truth be told, rather curious as to the
prisoner who spoke his language.
"Sit down," he said. "Now give me your word that you will not
attempt to escape, and I'll tell my men to stand away and to give
you breathing-space."
Seating himself upon the sand, in fact helped in the movement by
the man who had been holding him, Geoff remained for a while
panting heavily, while his guard, at a sharp order from the Turkish
officer, stepped aside and remained at some distance. Then Philip
and Esbul were brought along by the men who had captured them,
and were allowed to seat themselves beside him.
"Now," said the Turkish officer, after a while, when he was satisfied
that his prisoners were rested, "your promise. Say that you will make
no attempt at escape, and you shall march back to camp at my side
as friends, as you will, not as prisoners; only, when you arrive there,
it will be my duty to hand you over to the guard, and you must take
the consequences of your visit here this evening."
"We promise!" Geoff told him promptly.
"Then that is sufficient. Listen, my friend! Though I command a
detachment of Turkish troops down in this part of the world—this
terrible quarter, where there is nothing but sand and marsh and
water—yet I am from Constantinople, and, unlike many other Turks,
I have travelled somewhat. Thus it happens to have been my
fortune to have met many peoples, and amongst them men of your
country. Always I have heard that an Englishman's word is his bond.
My friend, you have given your word, and that is quite sufficient."
He showed his friendly spirit within a moment, for, diving a hand into
a pocket of his tunic, the officer produced a cigarette-case, and
handed it in turn to each of his prisoners; and then, as they sat on
there, on the sandy ridge above the twinkling camp-fires dotting the
hollow below them, this Turk became quite communicative, as
friendly as one could wish, chatted with Geoff as if he were an old
friend, one with whom he was well acquainted.
"Come!" he said encouragingly. "Be not so close, be as frank and as
friendly as I am, for let me tell you that I am more than interested in
you, for, as I said before, how many of your nation are there who
can speak our language? And you, you speak it as a native almost—
fluently, glibly, with the tone and accent of an educated gentleman.
That you are an officer I know, indeed I knew it from the moment of
your capture. Now tell me how it came about that you learnt our
tongue."
There was no doubt about his earnestness, nor about the fact that
his curiosity was purely friendly; quite frankly, therefore, withholding
nothing, Geoff told him how he had once, not so very long ago,
visited Mesopotamia, and how his travels had taken him as far as
Constantinople.
"I have a guardian," he told the Turkish officer, "a British officer, one
who for many years has taken the place of my dead father. He it was
who brought me to this country, who led me by the Tigris to
Bagdad, and with whom I sat in many an Arab camp making friends
with the natives."
"Wait! A British officer who led you to Bagdad! Who lived as a friend
with Arabs! But surely," said the Turk, "there is but one British officer
who could have done that, one with whom I am well acquainted.
Had it been a German now, there would be a host of them, though it
is little friends they are of the Arabs inhabiting these deserts; but
this man, listen my friend, I will give you his name—Douglas Pasha,
eh?"
"The same," Geoff admitted.
There was a long pause after that while the Turk slowly puffed at his
cigarette, the glowing end showing his features for a few brief
seconds, and then dying down between the puffs till it was only
possible to make out the dull outline of his figure. No doubt he was
thinking hard, thinking furiously, for a Turk, while he puffed clouds of
smoke into the dusk around him.
"So," he said at last, giving vent to a low-pitched whistle, "you are
Douglas Pasha's ward—and Douglas Pasha is an old friend of mine,
one to whom I am much beholden. Well, it is the fortune of war, my
friend. The fortune, or shall we say for a moment, while there are
none to overhear us, yes, the misfortune? For see the dilemma in
which I am placed. As a loyal Turk I have taken steps to make you a
captive, you, who were discovered in the act of watching our camp
and making a reconnaissance. As a loyal Turk I have made captive
the ward of one whom I admit my friend, one whom I would go far
to help, and whose esteem is of value to me. Yet, see the dilemma
in which I am placed. This I have done as a loyal man, and one who
does his utmost for his country; though all the while I know that it is
not my country for which I fight, but that Young Turk Party which,
alas! controls its destiny. Listen! There are none to hear us, and
therefore I can speak the words. Had the Sultan been able to control
the affairs of our nation, there would have been no war with Russia,
no war with our ancient friends the British, no alliance with these
hated Germans. There! I have said enough. Let us walk as friends as
far as our Head-quarters, and after that, well after that you pass out
of my hands, though Tewfic Pasha will think of you kindly, and
maybe might help you on some occasion."
Truly the adventure which had befallen Geoff and Philip and Esbul
was turning out to be as strange as it had been sudden and
unexpected; for here, captives in the hands of the enemy, they were
yet friends already with at least one of them, while Geoff had
discovered in this Turkish officer one who in other times would have
gone out of his way to be helpful, considerate, and friendly. But
Turkey was at war with Britain, and whatever Tewfic Pasha's private
feelings may have been towards our country he had a duty to
perform, like every other loyal man; and Geoff, realizing that fact,
honoured him the more when at length he gave a sharp order and
called his men about them.
"You'll fall in round the prisoners, allowing them to march freely," he
said. "When we reach the centre of the camp two of you will attach
yourselves to each of these three men, and will escort them to
Head-quarters. But listen, ye dogs! No violence, no brutal treatment,
for these young men have behaved most gallantly, have fought for
their freedom, and now, having lost to us, who are the more
numerous, are content with their lot, are cheerful, and are facing the
future with courage."
"After all, things might have been worse," chirped Philip, as the trio
marched along in the centre of their escort, the officer now at the
head of his men. "Quarter of an hour ago I thought my last moment
had come, particularly when one of these fellows round us indicated
to me in the most unpleasant manner that he was armed with a
knife, and was longing to push it through me. Ugh!"
He gave vent to an exaggerated grunt of horror, which set Geoff
giggling, for it reminded him of his own feelings, of that cold shiver
which had gone down his spine, of the extraordinary indescribable
shudder which had shaken him from head to foot, and which,
courageous though he hoped he had been, had set his limbs
trembling.
"Jolly nasty!" he said, sympathizing with his chum immediately. "I
had the same sort of experience, and it isn't nice, particularly on a
dark night, and when it comes so unexpectedly. But we've been
wonderfully lucky when you come to think of it—though it's awfully
unfortunate that we should have been captured—for this officer in
charge of the party actually knows Major Douglas, and if it weren't
war-time I believe he would himself see us to a place of safety."
"And might even now look the other way if there was a chance of
our escaping," suggested Phil.
"No, decidedly no!" Geoff answered. "He's loyal to the core, this
Turkish officer, unlike so many of them."
"Then what's to be done?" asked Phil. "You don't mean to tell me
that you are going to allow yourself to be taken as a prisoner, say,
into the interior of the country, and give up all hope of joining the
other fellows?"
Geoff laughed, a gruff, determined sort of laugh, which sounded
rather impressive in the darkness. There was a note of satire in it
too, a note seldom indulged in by our hero.
"Sorry that's the impression you've got of me after all these
months," he told Philip curtly. "Sorry you think I'm so soft, so lacking
in spirit, as to give up just because I am captured. What about that
trip we proposed which was to carry us to Bagdad, and was to allow
us to make a search for Major Douglas?"
A sudden exclamation escaped from Philip's lips, and, diving at
Geoff's arm, he gripped the wrist with a suddenness which was
almost disconcerting:
"And—and, why not?" he said in a hoarse whisper, "why not? Aren't
we now away from the expedition, aren't we more in the heart of
Mesopotamia than ever we were before? Just think for a moment,
and suppose you had gone off on that expedition that you've been
planning, that you've been dreaming about every day and night
since that letter came from your guardian. Supposing you'd slipped
away from the British camp and had got behind the enemy's lines:
where's the difference?"
Geoff brought his eloquence and enthusiasm to a somewhat sudden
end by giving him a disagreeable reminder.
"Difference! Difference!" he remarked caustically. "Only this, that
whereas, in that case, we should be behind their lines, but free; in
this, we are in the midst of their lines, not free, but captives."
But you could not damp Phil's ardour or his spirits however much
cold water you threw upon them. He gurgled for a while, gasped
rather loudly, and took to whistling. Then, when they had covered
perhaps a hundred yards, he again opened the subject; indeed, he
proceeded with the discussion as though it had never been broken
off, as if there had been no such thing as an interruption.
"Well," he said testily. "Well, who wants to be told that sort of thing?
Don't I know just as well as you do that the case ain't quite the
same, that we are prisoners and in the enemy's lines, instead of
being free and behind them? But it's near enough, surely. A chap
has only got to escape from these fellows who have bagged us, and
—and—and there you are!"
"And—and—there you are!" laughed Geoff, catching his enthusiasm
instantly; indeed, our hero had already been thinking furiously as to
how he and his friends were to circumvent this difficult position in
which they found themselves, and to shake off the hold which the
Turks had cast upon them. And why, as Philip said, if only they could
make their escape, seeing that they would then presumably be
behind the lines of the enemy, why should they not turn their faces
towards Bagdad, and go on with the rescue of Douglas Pasha.
"Jingo! We'll do it," he told his friend.
"You—you—you consent? You think it's possible?" asked Phil, his
voice eager, his face lit up—though, to be sure, it could not be seen
because of the darkness.
"Hush! We're in the centre of the camp, and the guard is closing in
on us," Geoff warned him. "But, just a last word in case we are
separated, I am going to do my best to escape, and if I succeed,
and can get you and Esbul free also, I am off for Bagdad."
"Done, with you! Shake hands on it!" cried Phil, gripping his chum's
palm and shaking it warmly. "Ripping! The thought of such an
expedition makes up for this ghastly business; perhaps to-night we'll
do it, perhaps to-morrow, and—and—well, you can rely on me
standing by you, old fellow. If they separate us, and the chance
comes to me to slip my cable, you know, don't you, Geoff, that I'll
stand by until I get you and Esbul out, so as to complete the party?"
There was no time for Geoff to make a reply, no time to thank his
chum for an expression of loyalty which was just like him, for the
guard had already closed in, men were gripping their arms on either
side, while, despite the caution of Tewfic Pasha, one at least of the
men showed little love for the captives.
"Dog," he whispered in Geoff's ear, "you infidel who speak our
language, be silent, or I will screw the head from your body."
"Unpleasant fellow," muttered Geoff, yet smiling serenely, for he
knew well enough that a call to Tewfic Pasha would relieve him of
this threatening fellow's attentions. "Ah! That appears to be the
Turkish Head-quarters."
It was lighter now that they had arrived at what appeared to be the
centre of the Turkish concentration; for numerous camp-fires were
dotted about the place, lighting up the surroundings with their
reflection, and indeed making the outer darkness even denser, even
more impenetrable. There loomed up now in front of them a row of
tents, one larger than the others, over which a flag could be heard
fluttering in the breeze, though its folds could not be seen so easily.
There were lamps burning in the tent, and towards it the guard
escorted their prisoners.
"Halt!" commanded Tewfic Pasha, and then entered the tent.
"Master," whispered Esbul at that moment, taking advantage of the
fact that the guard had released their grip of their prisoners, and
were now standing at attention dressed in two lines, one in front
and one behind their captives. "Master, let me say a word in your ear
while there is time. Listen! I am an Armenian."
It was a fact of which Geoff was thoroughly well aware, and yet a
fact the seriousness of which had not struck him till that moment.
"An Armenian! An Armenian, yes!" he said, speaking his thoughts in
a whisper; "and the Turks have no love for that nation."
"Love, Excellency!" exclaimed Esbul, with a bitterness which was
strange to him. "Love, my master! Of a truth, where the Armenian
race is concerned, the Turk has nothing but bitterness and hatred to
show. You have heard maybe of their doings in past years?"
"I have," Geoff said consolingly.
"How these Turkish fiends massacred our people, how they hate us
perhaps because we are Christians, and how they have done their
utmost to exterminate us, to grind us under their heel, to rid this
land of Turkey of us."
"I have heard the tale," Geoff told him sadly enough, for for many
years the massacre of unfortunate and helpless Armenians in Turkey
had been carried out by the Sultan's people, and had more than
once roused the bitter anger of peoples in Europe. Yet who could
control the Turk in the centre of his own country? What nation could
prevent the Sultan from wreaking his fiendish hate upon these
people? And now that this gigantic war had broken out, and Turkey
had declared herself in favour of the Germans, who could prevent
the agents of the Kaiser, those sinister individuals, from persuading
the Young Turk Party once more to commence their hideous work in
the neighbourhood of Erzerum and the Caucasus Mountains?
Already, urged on by those satellites of the Kaiser—those ruthless
individuals, possessed of as little mercy as their fellows in Europe—
massacres of the Armenians had once again begun, and ere they
were finished were to account for almost a million of these
miserable, unfortunate individuals. No wonder Esbul was trembling—
Esbul, the Armenian, the faithful servant who had followed Douglas
Pasha into the heart of Mesopotamia, and who had borne that
message to our hero.
"Master," he said again, making violent efforts to control his words,
"for you, who are a prisoner, and for your comrade, things may be
well enough, for at heart the Turk is kindly disposed, and thinks well
of the British, but for me, an Armenian, what is there to hope for?"
"What indeed?" Geoff sighed, when he grasped the full import of
what Esbul had been saying. For he knew well enough the hardships
of the Armenian race, and was well acquainted with the fact that the
Turks hated, despised, and tortured them. Were, then, these captors
of theirs likely to treat Esbul leniently once they discovered that one
of the trio they had laid their hands on was an Armenian? Would
they treat him as an honoured captive?—as Geoff hoped would be
the case with Philip and himself. Or would they drag him aside,
stand him out in the open, and shoot him like a dog?—the treatment
they were meting out to his brothers.
"Listen!" he told him. "Listen, Esbul; you must go, you must go now;
you must slip away; you must never let them see you! Wait! I will
fall to the ground and feign illness, which will create a disturbance.
Go then, take advantage of the opportunity; and, later, when you are
free, and perhaps have reached Bagdad, look out for me and my
comrade, and search for the whereabouts of Douglas Pasha."
He pressed the hand of the faithful fellow, and then, coughing
violently, suddenly fell to the ground and writhed there, rolling from
side to side, groaning and creating as much noise and fuss as was
possible. At once Philip leapt to his side, kneeling on the ground and
bending over him.
"What's the matter?" he asked distractedly, for he was thoroughly
startled by this strange occurrence.
"Shut up!" Geoff told him. "I'm shamming. I'll tell you why later."
"What ails the dog? Come, what has happened to him?"
Turks in the rear rank, drawn up behind the captives and nearest to
them, had darted forward almost at once as Geoff fell to the ground,
and now one of them bent over him and gripped him by the
shoulder, while he bawled into his ear. A second later a figure darted
from the tent—the figure of Tewfic Pasha—and, pushing men of the
front rank aside unceremoniously, came upon the scene.
"Hold your tongue!" he commanded the man shouting at Geoff.
"What has happened? Ah! This officer is ill. Carry him into the tent,
two of you idle fellows."
Picking their burden up, the men bore him into the tent, illuminated
by swinging oil-lamps, while Philip followed unbidden.
"And the third?" asked Tewfic Pasha, casting his eyes upon Geoff
and Philip, and seeing them clearly for the first time since he and his
men had laid hold of them. "The third, that other fellow; where is
he?"
Yes, where? There was a hue and cry outside: men were rushing to
and fro, shouting and bellowing at one another, while a couple of the
guard were speeding across the camp calling a warning to the
sentries. For Esbul had disappeared. He had been at Geoff's side just
a second before he tumbled, and those men in the rear rank of the
Turkish guard could have sworn that he had knelt beside his
comrade and had bent over him; and yet—and yet the darkness had
swallowed him up; he had gone, slipped away like a will-o'-the-wisp,
and no one had caught sight of him. Meanwhile Geoff had made a
reasonably rapid recovery, and stood now beside Philip, swaying just
a little—for he had to act the part—his face flushed just a trifle after
his exertions, his breath coming in panting grunts.
"I'm sorry," he told Tewfic Pasha; "but the thing is over now; merely
a spasm, a sudden dizziness, perhaps produced by those lusty
fellows of yours who sat so heavily on me."
"And the promise you made has been kept," Tewfic smiled back at
him, indeed his eyes twinkled—twinkled knowingly. "You gave me
your word that you and your comrades would march towards this
spot without attempting an escape, and when my guards laid their
hands on you, within sight of this tent, and marched you forward,
you were absolved of your promise. Listen!" he whispered in Geoff's
ear a moment or so later, when he had an opportunity. "It is as well,
my friend; it is just as well, for that other man was not of your
country. Maybe he was of ours, maybe he was an Armenian."
The bright friendly eyes of the Turkish officer twinkled again, and a
smile lit up his face, then, turning away, he accosted a Turk who
approached at that moment from an ante-room erected behind this
tent, which served as the Head-quarters of the Turkish
Concentration.
"Prisoners, Excellency!" he said. "We captured three of them on the
ridge, and doubtless they are scouts of an enemy party coming in
this direction. They are British officers, Excellency, and once they
were captured have behaved well and quietly. I have given them
your word—the word of a man of honour—that they shall be well
and kindly treated."
As a matter of fact, Geoff and Phil had no cause to complain of the
treatment meted out to them, for, as we have said before, the Turks
had already given many an illustration of the fact that they were
both good and stanch soldiers and most excellent fellows. Once the
fighting was done, once they had made captives or been captured,
they forgot their enmity, and in the case of those they had made
prisoners, treated them like human beings.
"You are to be sent up the Kut-el-Hai to the Tigris," said Tewfic
Pasha, when the General in Command of the Turkish Concentration
had inspected the prisoners and had cross-examined them. "I am
commanded to see that quarters are found for you, and that you are
given food and clothing. You will start on your journey to-morrow."
The following morning, in fact, at an early hour, found the two
young officers aboard a small steam-launch, which at once set out
for Kut-el-Amara. Arriving at that place on the River Tigris some
three days later, they transhipped to a larger vessel, a paddle-
steamer—as rusty and dilapidated as any of those which had come
to the Shatt-el-Arab from India for service with the British. Then they
were carried up the winding Tigris, and in due course, after days of
twisting and turning along the numerous bends of the river, after
running aground on sand-banks on many occasions, they reached at
last the city of Bagdad—the Mecca of the Turks of Eastern Turkey
and of the Arabs of Mesopotamia—and there, having been
interrogated again by a Turkish officer, they were sent to a prison—a
fort outside the city—the clanging gates of which shut on them with
a force and a jar which, in spite of their buoyant spirits, sent a chill
of despair through them.
"Nasty strong sort of a place," Philip whispered to his chum, as they
passed under a low flat roof and along a stone passage. "No picking
a hole through these walls with a penknife, my boy. It will have to
be a case of strategy."
Geoff looked round him, for the bright sunlight outside sent slanting
rays into the passage and lit up their surroundings.
"Beastly strong place," he agreed with Philip; "built of stone, and
every piece set close to the other. But we'll see, Phil; the cage that's
to hold the two of us will have to be a pretty strong one, for I'll tell
you this, I've made up my mind that I'll break out of this place, and
carry on that little business."
"Douglas Pasha, eh?" asked Phil.
"Of course. Ah! The fellow's opening a door, and in we go! A cell big
enough for the two of us! My word! Breaking out will take a lot of
doing."
 CHAPTER XV
Von Hildemaller's Intervention
A silence settled down upon the prison and the cell in which Geoff
and Philip had been thrust, once the clanging of the iron door which
closed it had subsided—a silence which told rather on their nerves,
and helped to rob them of their spirits. They sat just within the door,
staring about them, noticing with concern, almost with dismay, the
solid masonry built up above them, the two narrow windows which
gave air and light, and the absence of any sort of opening which
might give them a means of making their escape. Then Philip sat
down on the edge of a low platform built against one of the walls
and burst into loud whistling.
"No use being down-hearted! No use crying before we're hurt! In
other words, it ain't no use giving up before we've tried, eh?" he
blurted out when he had accomplished a few shrill bars of an air
popular amongst his fellows.
"In fact, keep on hoping!" said Geoff, laughing now, though he had
felt singularly depressed but a few moments earlier. "And, besides,
Philip, I've an idea!"
"Let's hear it; something new, eh? An idea! Well, you astonish me!"
The incorrigible subaltern began whistling again, a shrill, exultant,
happy whistle, and continued it though a moment later steps were
heard in the corridor outside. There was a bang on the door, and the
heavy iron concern was burst open. A smooth-faced, bald-headed,
and raggedly dressed Turk thrust his head and shoulders in and
grimaced at them. Then he opened his mouth, or rather let his lips
fall apart, showing a set of gleaming white teeth which perhaps
might have frightened younger people.
"Silence, dogs!" he shouted at them, and at the order Philip ceased
whistling.
"Tell the old boy that we want food and water," he said to Geoff.
"And, by the way, about that idea of yours, I suppose one can take it
that this rascal can't speak English."
Geoff gave him a quick look, and, turning, to the jailer, demanded
food and drink from him.
"As to calling us dogs," he said severely, realizing that to cringe to
this ruffian would be to invite harsh treatment, and that sternness
and unconcern on his part would be more likely to impress him—"as
to calling us dogs, you rascal, bear in mind that we are not without
friends in this country. Listen! You may know of one Tewfic Pasha?
Ah! You know the man then! That is enough—bring food and water."
It was clear in a moment that if this jailer were inclined to be a
somewhat rough and rude, if not a bullying, sort of individual, he yet
had a certain fund of discretion, and, moreover, that even if he were
the guardian of this cell, interned as it were, far away from active
operations, he yet had knowledge of others outside the prison. He
had heard of Tewfic Pasha, that was certain, for on the mention of
the name his face had fallen, the grimace, the snarl, which he had
turned upon the prisoners, was changed at once to a sly, fawning
smile, while he even bowed in Geoff's direction.
"I was mistaken then, Excellency," he said at last, after some
seconds had passed, during which he racked his brains for
something to say. "Food and water? You shall have it, for I have
orders to treat you with indulgence."
"Wait!" demanded Geoff, determined not to lose his hold over this
fellow, and arresting him in the act of closing the door, "wait, my
good fellow! Doubtless you will be caring for our comfort for some
while to come, so that it may be as well at this moment to come to
an understanding. Doubtless, too, money is of some value to you,
and if that be so, and you treat my comrade and myself to favours,
then, when we are released, you shall be rewarded. Say now, is that
a bargain?"
The man's face lit up immediately, while he even smiled quite a
pleasant smile upon them. Sour dispositioned, ill-grained, and surly
—perhaps because of the work allotted to him—this man, at the
bottom of his heart, was really not without his virtues. Cunning like
many a Turk, avaricious, and apt to trade upon those at his mercy,
he had—in spite of the order which he had just admitted he had
received—namely, that he was to treat his prisoners with indulgence
—in spite of that, he had looked upon them as helpless, as
penniless, as likely to be only a nuisance and an encumbrance. But
now Geoff's tones, the peremptory words he had uttered, and, more
than all, that suggestion of a reward quite altered his intentions.
"A reward, Excellency! Then indeed I am fortunate," he told Geoff.
"Let your Excellency declare what is wanted, and that which I am
able to bring shall surely reach you."
"And a question," said Geoff, determined to make the most of his
opportunity. "This prison, where is it situated? How far from
Bagdad?"
"A day's march—not more, not less, Excellency!"
"And there are other prisoners? Others from Britain or Russia?"
The man shook his head and raised his eyes as if Geoff were
encroaching upon a subject which was forbidden. Then, backing out
of the door, he pulled it to after him with a clang, and went off along
the passage in a different frame of mind from that in which he had
entered it. As for Phil, he gave vent once more to a shrill whistle,
which ended in a blast of air which came through his parted lips
soundless.
"And that's the idea?" he asked slyly, pointing at the door, and
jerking his thumb over his shoulder in the direction of the passage.
"If you put a bird in a cage, and the doors are so strong that
breaking through 'em is out of the question, that bird ain't
necessarily deprived of a chance of getting his freedom. There's the
door left, an iron affair on this occasion, and as strong as a rock
from the look of it, and then there's the jailer!"
"But there's something more than the jailer no doubt!" Geoff warned
him; "there'll be sentries perhaps, officials in charge of the prison,
other doors, with doors beyond them."
"Which don't say that even then we shouldn't be successful," said
Philip airily. "It's a chance, of course. What would they do if they
caught us?"
"Depends. Perhaps shoot us, though I hardly think it's likely—your
Turk doesn't indulge in frightfulness, like his German ally. It's worth
the chance, Philip, and we'll risk it; but, like sensible individuals, we'll
first of all find out as much as we can about local conditions. We'll
rest content here for a while and plumb this jailer fellow as far as
possible."
"And then we'll scrag him. Not that one wants to be violent with
him," said Philip; "I'd like to treat the fellow as gently as possible.
But where a man stands between you and a chance of getting
freedom, well, it ain't your fault, is it? It's his, if he gets hammered."
The two were still discussing the matter earnestly, almost eagerly,
when steps were heard again in the corridor outside, and the door
was pushed open by the jailer, now smiling widely, and bearing a
Turkish tray upon which were set coffee and food in abundance.
A week passed, during which Geoff and his chum did their best to
while away the weary hours, and to ascertain something of the
outside of their cell and the conditions existing in other parts of the
prison. By dint of carefully probing the jailer, by flattering him and
raising his hopes of a reward, they ascertained that the Governor
was lying ill, and that his subordinate was often enough away from
the building. There were troops there, they gathered, but how many,
and where quartered, no amount of questioning would extract from
the jailer; nor was it wise to ask him about the plan of the building,
the position of the cell, the corridor outside, and the road which led
to the gates giving access.
As to the cell itself, the first complete day had imprinted every
feature of it upon their minds, till they knew every crevice, every
flaw in the stone, every little hole and excrescence. They knew the
exact height of those two windows which admitted air and light to
their prison, and, by standing upon one another's shoulders, had
contrived to look outside—only to find that both windows looked out
upon a courtyard, surrounded by a wall the top of which would
undoubtedly be well beyond their reach. As to the windows
themselves, they were barred so heavily that to attempt to get
through them was out of the question, and even were they provided
with a saw or a chisel the job would still be beyond them.
"So it's got to be the jailer," grinned Philip, when the week had
passed, "and, 'pon my word, I'm awfully sorry about it. Of course we
must do the square thing by him; we've promised him a reward, and
he must have it. Let's form our plans for gagging and tying him up
safely."
There was more discussion after that, eager enough to be sure,
while plans were made and unmade, every eventuality likely to occur
foreseen and overcome as far as possible.
"Naturally enough, we shall not make the attempt until nightfall,"
said Geoff, "and, seeing that this fellow gives us a last call just about
dusk, that will be the most convenient hour to nab him. Let's go over
the scene for a moment. If we happen to be fairly close to the door
when he enters, he won't be suspicious, for he's found us in every
sort of position during the last week. A chap would get soft and out
of condition if he stayed in one place in a cell like this, and it's only
by walking up and down and running round that we have been able
to get exercise. Exercise, by Jove! Why didn't we think of that
before? We might have sent a message to the Governor of the
prison asking him to allow us out of our cell for certain hours of the
day, and that would have given us an idea of our surroundings."
It was strange indeed that they had not thought of that before, and,
acting on the impulse of the moment, they called loudly for the jailer,
and having attracted his attention sent him on a mission to the
Governor.
"But no, Excellency!" he told Geoff on his return; "it is not permitted
—not for the moment at any rate. You must wait. The Governor is in
ill-health and out of temper, and he bade me return with a
peremptory refusal. Have patience. Perhaps in a little while you will
be liberated and allowed to walk on the roof, where you may enjoy
the sunlight."
"Prophetic!" said Philip when the door had closed again. "In a little
while we may be liberated—this evening, if possible, I think. What
do you say, Geoff?"
"I'm with you," answered our hero; "let's get the gag ready for him,
and arrange about his money. Funny, isn't it, that we've been able to
keep what we had in our pockets? I imagine that if Germans had
captured us they'd have rifled us of every coin, and we should have
been paupers."
Yet, as it happened, despite their anxiety to break loose from the
prison and find their way into the open, the evening passed without
event, and was followed by days of waiting. Days which stretched
into weeks—miserable, lonely weeks, the hours of which dragged by
on leaden wheels, while the days themselves were often like a
nightmare, so long did the minutes take in passing, so long were
they drawn out, so utterly unending did they seem.
"But it's no use being despondent," said Geoff; "and just because
the jailer seems to be on the qui vive all the time, and has not yet
given us an opportunity, and, indeed, has been accompanied by
another man on many occasions, we mustn't think that the plan is
'off', or even dream of giving up the undertaking. We're going to
break out of this place, Philip."
"You've said that time and again," grinned the irrepressible and ever-
jovial Philip, "and so have I; and, by Jingo! we will—only when? This
waiting is getting a bit trying. I declare my joints are getting stiff,
and if I had to run a hundred yards I'd lose the race."
Lack of exercise and of fresh air was indeed telling upon the two
very greatly; for, be it remembered, they were young, enthusiastic,
and open-air creatures, who, in months past, had spent the better
part of their waking hours out in the free open air, under the blue
sky of Mesopotamia; and when in India or in England, outside
buildings whenever possible, enjoying the sunlight and the fresh
breezes which played about them. And now, to be cooped up
between four stone walls of this unpleasant prison, this stone vault,
was depressing, to say the least of it; it was enervating, taking the
colour out of their cheeks, and, in spite of their courage and their
youthful enthusiasm, was tending rather to take the heart out of
them.
"We shall rot if we go on like this," said Geoff desperately, when a
few days had passed. "I quite believe you, Philip, for my joints, too,
feel stiff and useless almost. Supposing we were to beguile the time
by a little active exercise—sort of Swedish gymnastics. Eh? Why
not?"
"Why not?" Philip said eagerly, grasping at the suggestion with the
energy almost of a drowning man grasping at a straw. "You've taken
squads in that before. Fire away, Geoff! Let's see what we make of
it."
Thereafter the astonished jailer peeped in more than once on these
curious white prisoners of his, to find them perhaps stretched on
their backs on the stone floor of the cell, their hands clasped under
their heads, and their legs, stretched stiffly in front of them, being
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