Heteroatom incorporation effect in σ- and π-electron systems: the sEDA(II) and pEDA(II) descriptors

The Journal of Organic Chemistry
Andrzej Mazurek, Jan Cz Dobrowolski

Abstract

The effect of heteroatom or heteroatomic group incorporation into unsaturated five- and six-membered cyclic systems was studied by means of DFT/B3LYP/aug-cc-pVDZ calculations. Two descriptors of the incorporation effect, sEDA(II) and pEDA(II), reflecting the influence of the incorporated atom or group on the population of the σ and π valence electrons, were constructed on the basis of natural bond orbital analysis. The sEDA(II) and pEDA(II) descriptors were shown to be linearly independent; the former correlated very well with electronegativity scales, whereas the latter correlated with NICS(1)(ZZ) and HOMA(CC) aromaticity indices. The two descriptors seem to be universal tools for analyzing different chemical and physicochemical effects occurring in unsaturated heterocyclic systems.

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Citations

Mar 5, 2014·The Journal of Chemical Physics·Michał F Rode, Andrzej L Sobolewski
Jun 18, 2017·The Journal of Physical Chemistry. a·Halina SzatylowiczTadeusz M Krygowski
Mar 28, 2013·Organic & Biomolecular Chemistry·Andrzej Mazurek, Jan Cz Dobrowolski
Apr 27, 2018·The Journal of Physical Chemistry. a·Jan Cz DobrowolskiGrażyna Karpińska
Jul 22, 2014·The Journal of Organic Chemistry·Tomasz SiodłaTadeusz M Krygowski
May 5, 2020·ACS Omega·Jan Cz Dobrowolski, Grażyna Karpińska
Aug 14, 2020·The Journal of Physical Chemistry. a·Takanori NagamiMasayoshi Nakano

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