Lewis acidity of group 14 elements toward intramolecular sulfur in ortho-aryl-thioanisoles

Teresita Munguia, Ioana S. Pavel, Ramesh N. Kapoor, Francisco Cervantes-Lee, László Párkányi, Keith H. Pannell

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The series of compounds (o-CH3SC6H 4)CH2EPh3 (E = Si (1), Ge (2), Sn (3), and Pb (4)) have been synthesized and characterized by NMR spectroscopy and by single crystal X-ray diffraction. Compounds 1 and 2 are isostructural with a triclinic crystal system and P-1 space group; however, morphotropic steps occur between Ge and Sn, and Sn and Pb. While the E-S distances in 1 and 2 are 3.985 and 3. 974 Å, respectively, ∼100% of the sum of the respective van der Waals (vdW) radii, there is a notable distortion from tetrahedral geometry about E. Compound 3 is also triclinic with P-1 symmetry, but has two molecules in the unit cell that demonstrate a distorted tetrahedral geometry and intramolecular Sn-S distances of 3.699 and 3.829 Å, 88% and 91% of the sum of the vdW radii. Compound 4 has a Pb-S distance of 3.953 Å (91% of ∑ vdW radii). The structure of the Grignard coupling product [o-(SCH3)C 6H4CH2]2 is also reported.

Original languageEnglish
Pages (from-to)1388-1397
Number of pages10
JournalCanadian Journal of Chemistry
Volume81
Issue number11
DOIs
Publication statusPublished - Nov 1 2003

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Keywords

  • Germanium
  • Intramolecular self-assembly
  • Lead
  • Silicon
  • Sulfur
  • Tin

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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