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Determining the excited‐state substituent constants σ CC ex of meta‐substituent from 3,4'‐disubstituted stilbenes
Author(s) -
Cao Chenzhong,
Sheng Bin,
Chen Guanfan
Publication year - 2012
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.3026
Subject(s) - substituent , chemistry , excited state , wavenumber , absorption (acoustics) , computational chemistry , photochemistry , medicinal chemistry , atomic physics , physics , acoustics , optics
In this paper, 61 samples of 3,4'‐disubstituted stilbenes and 18 samples of 3,3'‐disubstituted stilbenes were synthesized, and their UV data were measured in anhydrous ethanol. Based on the UV absorption energy (wavenumber) of 3,4'‐disubstituted stilbenes, the excited‐state substituent constants σ C C m ex of meta‐substituent were determined by means of curve‐fitting. The availability of σ C C m ex was confirmed by the good correlation with the UV absorption energy of 3,4'‐disubstituted stilbenes and 4,4'‐disubstituted stilbenes. Further, using the obtained constants σ C C m ex and the correlation equation, we calculated the UV wavenumbers of 3,3'‐disubstituted stilbenes, and the calculated wavenumbers are in good agreement with the experimental values. These results verified that the excited‐state substituent constants σ C C m ex of meta‐substituent are reliable parameter to scale the effect of meta‐substituent on the UV absorption energy. Copyright © 2012 John Wiley & Sons, Ltd.