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Diastereomers of 3-(S)-(1-phenylethyl)-5-methyl- and -5-phenylrhodanine: Crystal structures, conformations, and circular dichroism spectra

✍ Scribed by Knut Rang; Fen-Ling Liao; Jan Sandström; Sue-Lein Wang

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
156 KB
Volume
9
Category
Article
ISSN
0899-0042

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✦ Synopsis

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-H 2 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.

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