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Secondary solvent effects on the CD bands of thioamides

Authors
Journal
Spectrochimica Acta Part A Molecular Spectroscopy
0584-8539
Publisher
Elsevier
Publication Date
Volume
48
Issue
1
Identifiers
DOI: 10.1016/0584-8539(92)80201-7
Disciplines
  • Mathematics

Abstract

Abstract The CD spectra of simple thiolactams with fixed geometry, ( R)-3-methyl- and ( R)-5-methyl-2-pyrrolidinethione, reveal a pronounced solvent dependence. The changes in the spectral position of the n→π* CD band have been shown to arise from dimerization of the solute or from H-bond donor or acceptor interactions of the solvent. The spectral data due to secondary solvent effects can be fitted into Taft's solvatochromic equation and are explained by stabilization or destabilization brought about by H-bonding of the HOMO and LUMO of the thioamide chromophore.

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