ISSN:
0749-1581
Keywords:
Cyclohexanes
;
Decalins
;
Steroids
;
1H NMR substituent effects
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The proton shifts of trans-decalin and of its 9-hydroxy derivative were determined by 2D NMR methods, supported in the latter case by lanthanide-induced shifts. Based on these shifts and on literature data, substituent (X)-induced chemical shifts (SCS) were obtained for the 9-X-trans-decalins for X = OH, Cl, Br, I and Ch3. Comparisons with corresponding secondary cyclohexyl derivatives, derived from androstane measurements, usually showed good correlations; 38 SCS values out of 40 (for X = Hal, OH) deviate by 〈 ±0.08 ppm and are in line with earlier linear electric field effect calculations. Only two literature values for Br and I on the antiperiplanar tertiary H-10 exhibit unusual upfield shifts which, however, cannot be related to dihedral angle changes.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260260808
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