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Configurational and conformational study of new esters derived from 2‐methyl‐2‐azabicyclo[2.2.2]octan‐5‐ syn ( anti )‐ols by NMR spectroscopy and x‐ray crystallography—I
Author(s) -
Fernández M. J.,
Huertas R.,
Toledano M. S.,
Gálvez E.,
Server J.,
MartínezRipoll M.
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(199712)35:12<821::aid-omr181>3.0.co;2-7
Subject(s) - chemistry , octane , nuclear magnetic resonance spectroscopy , bicyclic molecule , spectroscopy , crystallography , stereochemistry , crystal structure , proton nmr , two dimensional nuclear magnetic resonance spectroscopy , carbon 13 nmr , organic chemistry , physics , quantum mechanics
A series of esters derived from syn ‐ and anti ‐2‐methyl‐2‐azabicyclo[2.2.2]octan‐5‐ols were synthesized and studied by 1 H, 13 C and 2D NMR spectroscopy. The crystal structure of 5‐ syn ‐(3,5‐dichlorobenzoyloxy)‐2‐methyl‐2‐azabicyclo[2.2.2]octane was determined by x‐ray diffraction. The unambiguous assignment of all bicyclic proton and carbon resonances was achieved by the combined analysis of the 1 H– 13 C correlation spectra and double resonance experiments. The 1 H– 1 H coupling constants are proposed as model values in order to carry out the analysis of other isoquinuclidine derivatives. In order to gain additional information, a conformational analysis using molecular modeling techniques was undertaken. © 1997 John Wiley & Sons, Ltd.