title: Heteroatom incorporation effect in σ- and π-electron systems: the sEDA(II) and pEDA(II) descriptors.
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.
authors.affiliation: National Medicines Institute, 30/34 Chełmska Street, 00-725 Warsaw, Poland.
authors.forename: Andrzej
authors.initials: A
authors.lastname: Mazurek
authors.forename: Jan Cz
authors.initials: JC
authors.lastname: Dobrowolski
mesh_terms: D055598:Chemical Phenomena; D053138:Cyclohexenes / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D004583:Electrons; D006571:Heterocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D053138:Cyclohexenes; D003517:Cyclopentanes; D006571:Heterocyclic Compounds