Woodward-Fieser’s Rules: Determining

Wavelength Max For Organic Compounds

Pada postingan kali ini saya akan membahas tentang Woodward-Fieser’s Rules. Woodward-
Fieser merupakan aturan yang dipergunakan dalam memprediksi penentuan panjang
gelombang suatu senyawa kimia. Dengan aturan ini kita bisa mengetahui berapa kira-kira
wavelength suatu senyawa kimia untuk berbagai keperluan. Untuk lebih jelasnya mari simak
penjelasan dibawah ini.

1. Diena

Heteroannular (transoid):base Homoannular (cisoid):base λmax

acyclic butadiene = 217 nm
λmax = 214 = 253
Group Increment
Extended conjugation +30
Additional homoannular +39
Each exo-cyclic C=C +5
Alkyl +5
-OCOCH3 +0
-OR +6
-SR +30
-Cl, -Br +5
-NR2 +60

2. Enone

Group Increment
6-membered ring or acyclic Base 215 nm
enone
5-membered ring parent enone Base 202 nm
Acyclic dienone Base 245 nm
X = H (aldehyde) Base 208 nm
X = OH, OR (aced, ester) Base 195 nm
Alkyl group or ring residue a, b, g and higher 10, 12, 18
-OH a, b, g and higher 35, 30, 18
-OR a, b, g, d 35, 30, 17, 31
-O(C=O)R a, b, d 6
-Cl a, b 15, 12
-Br a, b 25, 30
-NR2 b 95
Exocyclic double bond 5
Homocyclic diene component 39
Double bond extending 30
conjugation
Endocyclic double bond in a 5- 5
or 7-membered ring for X =
OH, OR
Solvent correction Increment
Water +8
Ethanol, methanol 0
Chloroform -1
Dioxane -5
Ether -7
Hydrocarbon -11

3. Aromatic Compounds

Parent Chromophore λ max

R = alkyl or ring residue 246
R=H 250
R = OH or O-Alkyl 230
G o m p
Alkyl or ring residue 3 3 10
-O-Alkyl, -OH, -O-Ring 7 7 25
-O– 11 20 78
-Cl 0 0 10
-Br 2 2 15
-NH2 13 13 58
-NHC(O)CH3 20 20 45
-NHCH3 73
-N(CH3)2 20 20 85