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Conformational Analysis of Substituted N ‐Nitroso‐ trans ‐decahydroquinolin‐4‐ones
Author(s) -
Natarajan D.,
Bhavani N.,
Manimekalai A.
Publication year - 1997
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199709)35:9<597::aid-omr125>3.0.co;2-o
Subject(s) - chemistry , moiety , piperidine , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , proton nmr , substituent , nitroso compounds , nitroso , carbon 13 nmr , organic chemistry
1 H and 13 C NMR resonance assignments and conformational assignments were carried out for four N ‐nitroso‐2‐phenyl‐ trans ‐decahydroquinolin‐4‐ones. In addition to conventional 1D NMR methods, 2D shift‐correlated NMR techniques ( 1 H– 1 H COSY, 1 H– 1 H NOESY and 1 H– 13 C HETCOR) were used for the signal assignments. At room temperature the title compounds exist in two isomeric forms. The preferred conformations of both the isomers of nitrosamines were determined by a comparison of the spectral data with those for the parent amines, and with the aid of substituent parameters. Molecular strain in nitrosamines is minimized by partial escape of the piperidine moiety into non‐chair conformation. © 1997 by John Wiley & Sons, Ltd.