Molecular and electronic structure of zwitterionic diamino-meta-quinonoid molecules

H. Thanh Le, P. C. Nam, V. L. Dao, T. VeszprÉMi, M. T. Nguyen

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Abstract

Quantum chemical calculations using molecular orbital (HF, CASSCF) and density functional theory (B3LYP) methods, in conjunction with the 6–311 + + G(d, p) basis set, have been applied to investigate the molecular and electronic structure of two diamino-meta-quinonoid molecules 1a and 2a, 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-CH3). It is confirmed that these substituted meta-quinone systems exhibit a zwitterionic structure in which the positively charged N-C-C(H)-C-N subunit, containing the two amino-groups, forms two chemical bonds with the negatively charged O-C-C(H)-C-O subunit. The negative charge amounts to about half of an electron. The charge separation has been approached in terms of geometries, vibrational frequencies, and electronic distribution. The ionization energy for molecule 1a is about 7.8±0.3eV. The quinonoid systems are essentially non-aromatic characterized by the NICS(+1) values of around 1.2 ppm.

Original languageEnglish
Pages (from-to)2347-2355
Number of pages9
JournalMolecular Physics
Volume101
Issue number15
DOIs
Publication statusPublished - Aug 2003

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ASJC Scopus subject areas

  • Biophysics
  • Molecular Biology
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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