Conformations of the thiathiophthenes and related molecules - Ab initio SCF-MO calculations

Stanley C. Nyburg, Giannoula Theodorakopoulos, Imre G. Csizmadia

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A conformational ab initio MO study has been carried out for the thiathiophthene molecule (TTP) and two related model compounds, thiomalonaldehyde (TMA) and its conjugate base (TMA(-)). The conformational energy surfaces for TMA, TMA(-) and TTP were generated using a least squares fit to the calculated data and plotted on a CALCOMP plotter. The results of the calculations showed that the cis-cis planar conformation of TTP is the most stable in agreement with experimental findings. For TMA and TMA(-) the cis-cis planar conformation is not the most stable. Contour plots of the five occupied π-MO's of TTP show great similarity to those of naphthalene. Less detailed calculations were carried out for 3-hydroxy-prop-2-en-1-thione (HPT) and 3-mercapto-prop-2-en-1-thione (MPT). HPT was shown to be most stable in the cis planar hydrogen bonded conformation in agreement with the experimentally obtained results. For MPT the non-hydrogen bonded planar structure was found to be the most stable.

Original languageEnglish
Pages (from-to)21-32
Number of pages12
JournalTheoretica chimica acta
Issue number1
Publication statusPublished - Mar 1 1977


  • Thiathiophthenes, conformations of ∼

ASJC Scopus subject areas

  • Chiropractics

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