Conformational analysis of mesocyclic polythioethers. Crystal and molecular structures of 1,4-dithiacycloheptane, 1,5-dithiacyclononane and 1,6-dithiacyclodecane

William N. Setzer, George S. Wilson, Richard S. Glass

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

The crystal and molecular structures of 1,4-dithiacycloheptane (1,4-DTCH), 1,5-dithiacyclononane (1,5-DTCN), and 1,6-dithiacyclodecane (1,6-DTCD) have been determined by single crystal X-ray studies. These compounds crystallize in the space groups P212121 (No. 19), P21/c (No. 14), and P21/n, respectively with a = 5.409(1), b = 10.883(2), c = 11.390(2) Å, Z = 4; a = 9.600(4), b = 12.378(8), c = 7.904(3) Å, /gb = 113.31(3)°, Z = 4; and a = 5.290(1), b = 12.853(3), c = 6.850(2) Å, β = 93.39(2)°, Z = 2, respectively. The nonhydrogen atoms were located using direct methods and the hydrogen atoms were found by Fourier difference maps. Full-matrix least-squares refinement led to conventional R factors of 0.0459, 0.0558 and 0.0314, respectively. The conformations adopted by 1,4-DTCH, 1,5-DTCN and 1,6-DTCD, in the crystalline slate, are twist chair (C2 symmetry), twist boat chair (C2 symmetry), and boat chair boat (C2k symmetry), respectively. The transannular S-S distances are 3.583, 4.108 and 4.864 Å, respectively.

Original languageEnglish (US)
Pages (from-to)2735-2742
Number of pages8
JournalTetrahedron
Volume37
Issue number16
DOIs
StatePublished - 1981

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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