Geometrical consequences of resonance-assisted intramolecular hydrogen-bond formation from Ab initio MO calculations on 2-nitroresorcinol

Charles W. Bock, István Hargittai

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

Ab initio orbital calculations on phenol, nitrobenzene, and 2-nitroresorcinol have been performed with the GAUSSIAN 92 series of programs. Initial RHF/6-31G* and RHF/6-31G** optimizations were followed by second-order MØller-Plesset MP2(FC)/6-31G* optimizations. The general geometrical features of these molecules, and, in particular, the characteristic changes as going from phenol to 2-nitroresorcinol and from nitrobenzene to 2-nitroresorcinol are in good agreement with recent gas-phase electron diffraction studies and with the notion of resonance-assisted intramolecular hydrogen-bond formation in 2-nitroresorcinol.

Original languageEnglish
Pages (from-to)307-312
Number of pages6
JournalStructural Chemistry
Volume5
Issue number5
DOIs
Publication statusPublished - Oct 1 1994

Keywords

  • 2-Nitroresorcinol
  • ab initio calculations
  • intramolecular hydrogen bond
  • molecular geometry

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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