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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

A New Index for the Estimation of the Aromatic Character - VIII

Author(s):

Volume 12, Issue 8, 2015

Page: [549 - 559] Pages: 11

DOI: 10.2174/157017861208150826115559

Price: $65

Abstract

A new aromaticity index is proposed based on the energy of π orbitals D={[π1n21n)]0 /[π1 + Σn21n)]} x a, where n are the number of occupied π orbitals and a is the number of cycles in the molecule. Calculations have been performed on aromatic and heteroaromatic compounds by using DFT method at B3LYP/6-311G+(d,p) level. This new index has been tested on a large number of 6π electron compounds, on bicyclic and polycyclic aromatic compounds and compared with HOMA and the aromatic stabilization energy (ASE). In all the cases, a good correlation has been found. In the case of HOMA, for monocyclic pentaatomic compounds different correlations was found depending on the nature, the number, and the position of the heteroatoms.

Keywords: Aromaticity, DFT, HOMA, ASE, quantification of the aromatic character.

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