ISSN:
0899-0042
Keywords:
3-(S)-(1-phenylethyl)-2-thioxo-2,3-dihydro-1,3-thiazol-4(5H)-ones
;
3-(S)-(1-phenylethyl)-rhodanines
;
CD spectra
;
empirical force field calculations
;
theoretical calculation of CD spectra
;
chromatographic diastereomer separation
;
triacetylcellulose
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
3-(S)-(1-phenylethyl)-5-methyl- and 5-phenyl-rhodanine have been studied by single crystal X-ray crystallography. The crystals of the 5-methyl compound were shown to contain equal amounts of the 5-(R) and 5-(S) diastereomers, while the crystals of the 5-phenyl compound only contain the 5-(S) diastereomer. The UV and CD spectra of the 5-H2 compound have been analyzed on the basis of CNDO/S calculations, and the CD spectrum has been reproduced by semiempirical calculations.The 5-methyl diastereomers can be partly separated by chromatography on triacetylcellulose, and the CD spectra of the individual forms can be evaluated. The 5-phenyl compound undergoes rapid epimerization in solution, and also for this compound the CD spectra of both forms can be evaluated. The contribution of the 5-substituent follows Ripperger's sector rule for dithiocarbamates. Chirality 9:568-577, 1997. © 1997 Wiley-Liss, Inc.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
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