Study of the substituent-influenced anomeric effect in the ring-chain tautomerism of 1-alkyl-3-aryl-naphth[1,2-e][1,3]oxazines

István Szatmári, Diána Tóth, Andreas Koch, Matthias Heydenreich, Erich Kleinpeter, Ferenc Fülöp

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Abstract

The stabilities of the trans (B) and cis (C) tautomeric ring forms that are experimentally observed in the ring-chain tautomeric interconversion of 1-alkyl-3-aryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines has been investigated. Stability differences are explained by the analysis of the natural bond orbital results for the lone pairs of electrons that are on the heteroatoms in the oxazine ring system and by regression analysis of the calculated 13C NMR chemical shift values.

Original languageEnglish
Pages (from-to)4670-4675
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number20
DOIs
Publication statusPublished - Oct 13 2006

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Keywords

  • Ab initio calculations
  • Anomeric effect
  • Conformational analysis
  • NBO analysis
  • Naphthoxazines
  • Ring-chain tautomerism

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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