Conformational NMR study of N-substituted-1,3,4,5-tetrahydro-1H-2-benzazepines

Autor:	Novruz G. Akhmedov, Alan R. Katritzky, Ion Ghiviriga, Rexiat Maimait
Rok vydání:	2002
Předmět:	chemistry.chemical_compound Benzazepines chemistry Stereochemistry Proton NMR Carbon-13 NMR Ring (chemistry) Two-dimensional nuclear magnetic resonance spectroscopy Vicinal Spectral line Benzazepine
Zdroj:	Journal of the Chemical Society, Perkin Transactions 2. :1986-1993
ISSN:	1364-5471 1472-779X
DOI:	10.1039/b208633f
Popis:	The variable temperature (298–179 K) 1H NMR spectra of N-substituted 2-benzazepines (compounds 2–7) correspond to two puckered mirror-image (enantiomorphic) conformations, with a single chair-to-chair interconversion barrier for the benzazepine ring of ca. 11 kcal mol−1 in CD2Cl2 solution. A similar interconversion was detected for 1,3,4,5-tetrahydro-N-methylbenzazepine (compound 1), of lower symmetry. The conformations of compounds 1–7 were assigned on the basis of the magnitude of 1H-1H vicinal coupling constants. The 1H and 13C NMR spectral assignments were determined by 1H–1H COSY, 1H–13C COSY, and NOESY experiments.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e90d05db58c464dea720f820fbeb14a7 https://doi.org/10.1039/b208633f Zobrazit plný text záznamu