Strong intramolecular hydrogen bonding within the dimedone-aldehyde adducts

Mark Sigalov, Radion Vainer, Vladimir Khodorkovsky

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Ionization of the well-known 2:1 dimedone-aldehyde adducts in polar solvents leads to the respective monoanions involving the intramolecular ionic hydrogen bond. These anions feature the short O⋯Ha⋯O distance (2.403 Å for 4, R=p-ClC6H4) and the strong downfield shift of the corresponding signal (δHa = 17.0 ppm, in dichloromethane-d2). The negative charge is delocalized over the two dimedone moieties. This phenomenon is also reproduced by quantum mechanical calculations. The dynamic NMR spectra provide an estimate of the hydrogen bond energy as high as 16 kcal/mol.

Original languageEnglish
Pages (from-to)230-236
Number of pages7
JournalJournal of Molecular Structure
Volume977
Issue number1-3
DOIs
StatePublished - 10 Aug 2010

Keywords

  • Dynamic NMR
  • Ionic hydrogen bonds
  • Theoretical calculations

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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