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Aromaticities of azines relative to benzene; a theoretical approach through the dimethyldihydropyrene probe
Author(s) -
Nisa Riffat U.,
Hanif Muhammad,
Mahmood Adeem,
Ayub Khurshid
Publication year - 2014
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.3348
Subject(s) - aromaticity , chemistry , azine , benzene , chemical shift , computational chemistry , antiaromaticity , organic chemistry , molecule
The aromaticities of azines relative to benzene have been estimated by fusion with 15,16‐dimethyldihydropyrene. Chemical shift data for the azine‐fused dihydropyrenes (calculated at GIAO HF/6‐31G*//B3LYP/6‐31 + G*) were used to estimate the reduction in the dihydropyrene nucleus aromaticity. Choice of the saturated reference model was quite crucial in reliable estimation of aromaticity. Reference models with partial unsaturation at azine (21,23,25–32) gave better estimate of aromaticity than the parent dimethyldihydropyrene. Aromaticities of azines through chemical shift data and geometric parameter analysis were found to be 90–100% to that of benzene, highly consistent with the aromaticity estimation by nucleus independent chemical shift (0)πzz calculations. Copyright © 2014 John Wiley & Sons, Ltd.