The electron density of delocalized bonds (EDDB) applied for quantifying aromaticity

Abstract

In this study the recently developed electron density of delocalized bonds (EDDB) is used to define a new measure of aromaticity in molecular rings. The relationships between bond-length alternation, electron delocalization and diatropicity of the induced ring current are investigated for a test set of representative molecular rings by means of correlation and principal component analyses involving the most popular aromaticity descriptors based on structural, electronic, and magnetic criteria. Additionally, a qualitative comparison is made between EDDB and the magnetically induced ring-current density maps from the ipsocentric approach for a series of linear acenes. Special emphasis is given to the comparative study of the description of cyclic delocalization of electrons in a wide range of organic aromatics in terms of the kekulean multicenter index KMCI and the newly proposed EDDBk indexThe research was supported in part by the Faculty of Chemistry at Jagiellonian University (grant K/DSC/001469, DS), Foundation for Polish Science (FNP START 2015, stipend 103.2015, DS), National Science Centre, Poland (NCN SONATA, grant 2015/17/ D/ST4/00558, DS) as well as the PL-Grid Infrastructure of the Academic Computer Centre CYFRONET with the calculations performed on the cluster platform ‘‘Prometheus’’. MS thanks for the support of the Ministerio de Economa y Competitividad of Spain (Project CTQ2014-54306-P), Generalitat de Catalunya (project number 2014SGR931, Xarxa de Refere`ncia en Qumica Teo`rica i Computacional, and ICREA Academia prize), and European Fund for Regional Development (FEDER grant UNGI10-4E-801

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