Presentation of a new index for estimation of aromaticity in halo- and cyanobenzenes: The role of potential energy in aromaticity

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Abstract

A linear correlation has been obtained between average values of Hamiltonian kinetic energy ( math formula) and potential energy ( math formula) calculated at the bond critical points using atoms in molecules method. This relation was used to introduce a new index ( math formula) for estimation of aromaticity in halo- and cyanobenzenes. Potential energy has different terms such as attraction between nuclei and electrons, also repulsion of electrons which affect the inertia and mobility of electrons, respectively. Therefore, contribution of potential energy in this relation must be controlled. Contribution of potential energy in aromaticity has been managed using a fitting parameter. This parameter was obtained by fitting the aromaticity stabilization energy data with values of aromaticity calculated by math formula index for halo- and cyanobenzenes. The contribution of potential energy in math formula index is complete when molecule is nonaromatic and is negligible when molecule is antiaromatic. Indeed, molecule is aromatic when contribution of potential energy in math formula index lies between above limits. © 2013 Wiley Periodicals, Inc.

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