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3-Benzyl-5-phenyl-2-p-tolylthiophene

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

The crystal structure of a substituted thiophene derivative was determined. Its planar thiophene ring and bond angles are similar to unsubstituted thiophene, with phenyl rings showing steric rotations.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Materials Science

Background:

  • Thiophene derivatives are important heterocyclic compounds with diverse applications.
  • Understanding the crystal structure of substituted thiophenes provides insights into their chemical properties and potential uses.
  • Previous studies have characterized various thiophene structures, establishing a baseline for comparison.

Purpose of the Study:

  • To elucidate the crystal structure of 3-benzyl-5-phenyl-2-p-tolylthiophene.
  • To analyze the planarity of the thiophene ring and compare its structural parameters with unsubstituted thiophene.
  • To investigate the steric interactions and rotational angles of the substituent groups (benzyl, phenyl, and p-tolyl) relative to the thiophene core.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional atomic arrangement.
  • Crystallographic data were collected and analyzed to obtain bond lengths, bond angles, and torsion angles.
  • Structural parameters were compared with those of known thiophene compounds.

Main Results:

  • The crystal structure of 3-benzyl-5-phenyl-2-p-tolylthiophene (C24H20S) was successfully determined.
  • The thiophene ring was found to be planar, with C-S bond distances of approximately 1.73 Å and a C-S-C bond angle of 92.3°.
  • Steric repulsion between the p-tolyl and benzyl groups caused a rotation of 56.1° for the p-tolyl group out of the thiophene plane, while the phenyl group at C(5) was rotated by 36.9°.

Conclusions:

  • The determined crystal structure confirms the planarity of the thiophene core in this substituted derivative.
  • The observed rotational angles of the phenyl and p-tolyl groups are significant and influenced by steric factors.
  • The structural similarity to unsubstituted thiophene suggests conserved electronic properties, while steric effects may influence intermolecular interactions and material properties.

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