A study of the stereochemistry and electronic transitions of cyclic and acyclic thioamides by crystallography, spectroscopy and computational methods

University dissertation from Organic Chemistry 1, Kemicentrum, Lund University

Author: Knut Rang; Lunds Universitet.; Lund University.; [1998]

Keywords: NATURVETENSKAP; NATURAL SCIENCES; rotational barriers UV and CD spectroscopy DNMR X-ray N -bis[ S -1-phenylethyl]-thiourea N attractive steric effect chiral phenyl or H- rhodanines 3- alkyl or aralkyl -5- methyl Conformations electronic transitions molecular mechanics enantiom Organic chemistry Organisk kemi;

Abstract: Analysis of conformations and electron transitions of 3-(alkyl or aralkyl)-5-(methyl or phenyl)rhodanines with analogues and N,N'-bis[(S)-1-phenylethyl]-thiourea have been performed by X-ray crystallography, 1H NMR, molecular mechanics, ultraviolet spectroscopy and for the chiral rhodanines, enantiomer chromatography and circular dichroism spectroscopy. The magnitude of rotational barriers has been determined. Attractive steric effect is determined in the syn form of 3-neopentyl-5-phenylrhodanine. Absolute configurations are determined for the anti and syn forms of 3-(S)-(1-phenylethyl)-5-methylrhodanine. A special study is made with the N-[(S)-(1-phenylethyl)]-dithiocarbamate anion and the equilibrium of its ammonium salt.

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