Chemical bonding in zwitterionic diamino-meta-quinonoids and their isomers

Tibor Höltzl, Tamás Veszprémi, Minh Tho Nguyen

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Quantum chemical calculations using molecular orbital (HF) and density functional (B3LYP) methods, in conjunction with the 6-311++G(d,p) basis set, have been applied to investigate the electronic structure of a series of diamino-meta-quinonoid molecules, each containing a six-membered ring coupled with two exocyclic C=O bonds situated in a meta position, along with two amino substituents (NH2 and NH - R). The chemical bonding phenomena in these zwitterions and isomers where one or two hydrogens are transferred from N- to O- are analyzed with the aid of the atoms-in-molecules (AIM) approach. The relative energies between zwitterionic and quinonoid isomers in both neutral and ionized states also have been evaluated. Substituents exert a strong effect that in many cases changes the energy ordering.

Original languageEnglish
Pages (from-to)1123-1131
Number of pages9
JournalJournal of Physical Organic Chemistry
Volume18
Issue number11
DOIs
Publication statusPublished - Nov 1 2005

Keywords

  • Ab initio calculations
  • Atoms-in-molecules analysis
  • Density functional theory
  • Diamino-meta-quinonoid structures
  • Substituent effects
  • Zwitterion structures

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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