Aromaticities of azines relative to benzene; a theoretical approach through the dimethyldihydropyrene probe

Journal Article

Ayub, Maria1, Riffat U. Nisa1, Muhammad Hanif, Adeem Mahmood andKhurshid . 2014

• Publication Work Type: Research
• Publication Online URL: J. Phys. Org. Chem
• Volume Number: 27
• Pages: 860–866

Publication Abstract

The aromaticities of azines relative to benzene have been estimated by fusion with 15,16-dimethyldihydropyrene. Chemicalshift data for the azine-fused dihydropyrenes (calculated at GIAO HF/6-31G*//B3LYP/6-31 + G*) were used to estimate thereduction 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 aroma-ticity than the parent dimethyldihydropyrene. Aromaticities of azines through chemical shift data and geometric parameteranalysis were found to be 90–100% to that of benzene, highly consistent with the aromaticity estimation by nucleus indepen-dent chemical shift