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Effect of substituent on the UV–Vis spectra: an extension from disubstituted to multi‐substituted benzylideneanilines
Author(s) -
Wang Linyan,
Cao Chaotun,
Cao Chenzhong
Publication year - 2016
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3533
Subject(s) - substituent , chemistry , context (archaeology) , computational chemistry , medicinal chemistry , paleontology , biology
For studying the substituent effects on the ν max of substituted benzylideneanilines (XBAYs) systematically, 12 samples of 3,3′‐disubstituted XBAYs and 52 samples of multi‐substituted XBAYs were synthesized, and the substituent effects on their ν max were investigated in this paper. A modified regression equation quantifying the ν max of 4,4′/4,3′/3,4′/3,3′‐disubstituted and multi‐substituted XBAYs (shown as Eq. [Disp. Item 3. νmax=32032.64−666.51σXp+633.01∑σYm+1262.32σYp−808.82∑σCCexm+1629.15∑σCCexp−931.08Δ∑σ2−194.83Δ∑σCCex2 ...]) was obtained. The results showed that the substituent effects on the ν max of 3,3′‐substituted and multi‐substituted XBAYs became more complicated. In Eq. [Disp. Item 3. νmax=32032.64−666.51σXp+633.01∑σYm+1262.32σYp−808.82∑σCCexm+1629.15∑σCCexp−931.08Δ∑σ2−194.83Δ∑σCCex2 ...], the contributions of the meta‐parameters to the ν max of XBAYs were different from those of the corresponding para‐parameters. For the substituent cross‐interaction effects, there is no difference whatever the substituents are at meta‐position or para‐position. Compared with Eq. [Disp. Item 1. νmax=32119.79−718.51σX+1197.18σY−1017.23Δσ2+1632.49∑σCCex−229.53ΔσCCex2 ...], Eq. [Disp. Item 3. νmax=32032.64−666.51σXp+633.01∑σYm+1262.32σYp−808.82∑σCCexm+1629.15∑σCCexp−931.08Δ∑σ2−194.83Δ∑σCCex2 ...] obtained in this paper has a wider application and more accuracy in quantifying the ν max of substituted XBAYs. Copyright © 2016 John Wiley & Sons, Ltd.