ISSN:
0749-1581
Keywords:
1H NMR
;
Hindered rotation
;
Phenyl, formylmethylamino and formyl groups
;
3-Formylmethylamino-1,2,3-triphenylpropyl chlorides
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Unusually high free energies of activation for the rotation of phenyl groups, 12.1 and 11.1 kcal mol-1, are observed in the (1R*, 2S*, 3S*) and (1R*, 2R*, 3S*) isomers of 3-(formylmethylamino)-1,2,3-triphenylpropyl chloride, and for the rotation of the formylmethylamino group (11.7 kcal mol-1) in the Z rotamer of the former isomer. These high barriers can be related to the interdependence of the rotation of such large planar groups in the strongly biased preferred conformations. The barriers for rotation of the formyl group are in the usual range (22.5 and 20.6 kcal mol-1) for (1R*, 2S*, 3S*) and (1R*, 2R*, 3S*) isomers, respectively.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260260707
Permalink