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(1Z,3Z)-1,4-diphenyl-1,4-bis(p-tolylmethylthio)-1,3-butadiene

F Freeman1, H Lu, J W Ziller

  • 1Department of Chemistry, University of California, Irvine 92717, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|April 15, 1995
PubMed
Summary

This study details the crystal structure of a diphenyl-bis-(p-tolylmethylthio)-butadiene compound. Its unique s-trans conformation and shorter-than-expected carbon-carbon bonds suggest significant electronic delocalization effects.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Understanding the structural nuances of conjugated systems is crucial for predicting their chemical behavior.
  • Butadiene derivatives with sulfur-containing substituents offer unique electronic properties.

Purpose of the Study:

  • To elucidate the crystal structure of (1Z,3Z)-1,4-diphenyl-1,4-bis-(p-tolylmethylthio)-1,3-butadiene.
  • To analyze the bond lengths and conformation of the butadiene core in the presence of bulky thioether substituents.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular structure.
  • Analysis of bond lengths, bond angles, and conformational parameters.

Main Results:

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  • The compound adopts an s-trans conformation.
  • The C(2)--C(2') single bond (1.432 Å) is shorter than in unsubstituted 1,3-butadiene.
  • The C(1)--C(2) double bond (1.350 Å) is comparable to that in 1,3-butadiene.

Conclusions:

  • The observed bond lengths suggest significant electronic delocalization within the butadiene unit.
  • Factors such as resonance, hybridization, and the presence of sulfur atoms likely contribute to the structural characteristics.