Intra- and intermolecular N-H⋯O hydrogen bonds in pyrrolyl derivatives of indane-1,3-dione - Experimental and theoretical study

M. Sigalov, B. Shainyan, N. Chipanina, I. Ushakov, A. Shulunova

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

2-(Pyrrol-2-ylmethylene)-1,3-indandione (4) and 2-(pyrrol-2-ylmethylene)-3- dicyanomethylidene-1-indanone (5) were synthesized. Multinuclear and 2D-NMR, IR, UV spectroscopic investigations as well as quantum chemical calculations showed the presence of strong hydrogen bonding in these molecules. For both molecules, the presence of two conformers, with and without H-bond, was experimentally detected in the basic solvents (DMSO, acetone, pyridine) and the solvate complexes were theoretically calculated. Specific behavior of the intramolecular H-bonded complexes different from that of the intermolecular H-complexes is discussed.

Original languageEnglish
Pages (from-to)1178-1187
Number of pages10
JournalJournal of Physical Organic Chemistry
Volume22
Issue number12
DOIs
StatePublished - 1 Dec 2009

Keywords

  • Density functional theory
  • Hydrogen bonds
  • IR
  • NMR spectroscopy
  • Quantum chemical calculations
  • UV

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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