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Substituent effects on the stretching vibration of C═N in multi‐substituted benzylideneanilines
Author(s) -
Wang Linyan,
Cao Chaotun,
Cao Chenzhong
Publication year - 2019
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.3969
Subject(s) - substituent , chemistry , excited state , analytical chemistry (journal) , computational chemistry , stereochemistry , organic chemistry , quantum mechanics , physics
Forty‐nine samples of 3,4′/4,3′/3,3′‐disubstituted benzylideneanilines (XBAYs) and 52 samples of multi‐substituted XBAYs were synthesized, and their infrared absorption spectra were recorded in this paper. On the basis of the stretching vibration frequencies ν C═N of C═N bridging bond of 158 samples of substituted XBAYs (including 57 samples of 4,4′‐disubstituted XBAYs from reference and 101 samples of substituted XBAYs synthesized in this paper), an extensional research of substituent effects on the ν C═N values from 4,4′‐disubstituted XBAYs to multi‐substituted XBAYs was made. A modified equation for quantifying the ν C═N values of multi‐substituted XBAYs was obtained (shown as Equation (3)). Equation (3) indicates that the excited‐state substituent constant of Y and the substituent specific cross‐interaction effect between X and X cannot be ignored for the quantitative regression analysis of the ν C═N values of multi‐substituted XBAYs. Compared with Equation (1), Equation (3) has a wider application and more accuracy in quantifying the ν C═N values of substituted XBAYs.