NMR spectroscopic and computational study of conformational isomerism in substituted 2-aryl-3 H -1-benzazepines: Toward isolable atropisomeric benzazepine enantiomers Academic Article uri icon

Overview

MeSH Major

  • Benzazepines
  • Quantum Theory

abstract

  • Certain 2-aryl-3H-1-benzazepines are conformationally mobile on the NMR time scale. Variable-temperature NMR experiments bolstered by calculations indicate that alkylation of the azepine ring will slow the interconversion of conformational enantiomers markedly. DFT studies show that, while the substitution patterns of the aryl groups at C2 and C4 do not exert large effects on the rate of enantiomerization, alkylation at C5 slows it appreciably. Alkylation at C3 slows enantiomerization even more, possibly to the extent that isolation of atropisomers might be attempted.

publication date

  • August 16, 2013

Research

keywords

  • Academic Article

Identity

Language

  • eng

Digital Object Identifier (DOI)

  • 10.1021/jo4013089

PubMed ID

  • 23848431

Additional Document Info

start page

  • 8028

end page

  • 36

volume

  • 78

number

  • 16