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1 H and 13 C NMR study of a series of C‐9‐substituted 19‐norsteroids
Author(s) -
Dallery Laurence,
Bertigny JeanPierre,
Doussot Joel,
Garreau Robert,
Guy Alain,
Platzer Nicole
Publication year - 2002
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.428
Subject(s) - chemistry , heteronuclear molecule , chemical shift , multiplet , nmr spectra database , coupling constant , carbon 13 nmr , two dimensional nuclear magnetic resonance spectroscopy , nuclear magnetic resonance spectroscopy , computational chemistry , spectral line , stereochemistry , crystallography , physics , particle physics , astronomy
The 1 H and 13 C NMR spectra of a series of 9‐substituted 19‐norsteroids were completely assigned using a series of 2D NMR experiments, which included 1 H– 1 H COSY, NOESY and 1 H– 13 C heteronuclear HETCOR and HMQC. For second‐order spin systems, chemical shifts and coupling constants were obtained by simulation of the experimental spectrum. Criteria were deduced to characterize the stereochemistry of these different compounds (multiplet pattern of H‐8β and variation of chemical shifts). The results allow the easy determination of the configuration at C‐9. Conformational changes resulting from the substitution were studied by NMR and molecular modeling calculations (AM1). Copyright © 2001 John Wiley & Sons, Ltd.