title: NMR spectroscopic and computational study of conformational isomerism in substituted 2-aryl-3H-1-benzazepines: toward isolable atropisomeric benzazepine enantiomers.
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.
authors.affiliation: Department of Natural Sciences, Baruch College of the City University of New York, 17 Lexington Avenue, New York, New York 10010, USA. keith.ramig@baruch.cuny.edu
authors.forename: Keith
authors.initials: K
authors.lastname: Ramig
authors.forename: Edyta M
authors.initials: EM
authors.lastname: Greer
authors.forename: David J
authors.initials: DJ
authors.lastname: Szalda
authors.forename: Sasan
authors.initials: S
authors.lastname: Karimi
authors.forename: Allen
authors.initials: A
authors.lastname: Ko
authors.forename: Laura
authors.initials: L
authors.lastname: Boulos
authors.forename: Jiansan
authors.initials: J
authors.lastname: Gu
authors.forename: Nathan
authors.initials: N
authors.lastname: Dvorkin
authors.forename: Hema
authors.initials: H
authors.lastname: Bhramdat
authors.forename: Gopal
authors.initials: G
authors.lastname: Subramaniam
mesh_terms: D001552:Benzazepines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D001552:Benzazepines