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On the incorporation effect of the ring‐junction heteroatom. The sEDA(III) and pEDA(III) Descriptors
Author(s) -
Mazurek Andrzej,
Dobrowolski Jan Cz.
Publication year - 2015
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3409
Subject(s) - heteroatom , chemistry , electronegativity , ring (chemistry) , aromaticity , conjugated system , valence (chemistry) , population , stereochemistry , computational chemistry , molecule , organic chemistry , polymer , demography , sociology
Descriptors of the heteroatom incorporation effect in the ring‐junction position, sEDA(III) and pEDA(III), are introduced for the first time. They express the change in the σ and π valence electron population produced by the heteroatom. The sEDA(III) descriptor is a good measure of electronegativity of ring‐junction incorporants. Unexpectedly, the pEDA(III) descriptor does not correlate with π‐electron characteristics because the ‘aromatic’ bond pattern in the considered fused ring systems depends on the incorporants' change within the group or period of the periodic system. We found that the HOMA aromaticity index of conjugated paths is useful to trace π‐electron flows in heteroatom‐incorporated polycyclic (aromatic) systems. Copyright © 2014 John Wiley & Sons, Ltd.