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Woodward

The document outlines Woodward-Fieser rules for estimating UV absorption of conjugated systems like dienes, benzoyl derivatives, and enones. It provides increments in nanometers to estimate λmax based on functional groups and their position. For example, an extended conjugation in a diene adds 30nm, each exo-cyclic double bond adds 5nm, and an alkyl group adds 5nm. Substituents like -OH, -OCH3 on a benzoyl derivative in the ortho or meta position adds 7nm or 25nm in the para position. α and β substitutions on an enone usually add 10-35nm depending on the specific group.

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93 views1 page

Woodward

The document outlines Woodward-Fieser rules for estimating UV absorption of conjugated systems like dienes, benzoyl derivatives, and enones. It provides increments in nanometers to estimate λmax based on functional groups and their position. For example, an extended conjugation in a diene adds 30nm, each exo-cyclic double bond adds 5nm, and an alkyl group adds 5nm. Substituents like -OH, -OCH3 on a benzoyl derivative in the ortho or meta position adds 7nm or 25nm in the para position. α and β substitutions on an enone usually add 10-35nm depending on the specific group.

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Ppa Gpat Amit
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Table 1: Woodward-Fieser Rule for Dienes

Group Increment
Extended conjugation +30
Each exo-cyclic C=C +5
Alkyl +5
-OCOCH3 +0
Homoannular diene 253 nm
-OR +6 Heteroannular diene 215 nm
-SR +30
-Cl, -Br +5
-NR2 +60
Table 2: Woodward-Fieser Rule for Benzoyl Derivatives
Group
O

C R

R= alkyl or ring residue 246 nm


R= H 250 nm
R= OH or alkoxy 230 nm
Substituent Position Increment
alkyl or ring residue O, m 3
P 10
-OH, OCH3 O,m 7
P 25
-O Ortho 11
Meta 20
Para 78
-Cl O, m 0
P 10
-Br O, m 2
P 15
-NH2 O, m 13
P 58
-NHCOCH3 O, m 20
P 45
Table 3: Woodward-Fieser Rule for Enones
Group Increment
6-membered ring or acyclic enone Base 215 nm
5-membered ring parent enone Base 202 nm
Acyclic dienone Base 245 nm
Substituent
Double bond extending conjugation 30
Alkyl group or ring residue α, β, γ and higher 10, 12, 18
-OH α, β, γ and higher 35, 30, 18
-OR α, β, γ , δ 35, 30, 17, 31
-O(C=O)R α, β, δ 6
-Cl α, β 15, 12
-Br α, β 25, 30
-NR2 Β 95
Exocyclic double bond 5
Homocyclic diene component 39

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