Theoretical studies on transannular S-S interactions in geometrically constrained 1,5-dithiocane derivatives

Richard S. Glass, Ludwik Adamowicz, Jeffrey L. Broeker

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Vibronic analysis on naphtho[1,8-b,c]-1,5-dithiocin (10) and naphtho[1,8-b,c]-1,5-dithiocin-1-oxide (11) using the Hartree-Fock method with the STO-3G basis set shows no evidence for covalent-bond formation in 11 compared with 10. Thus the transannular interaction in 11 is due to electrostatic interaction and not incipient sulfurane formation. Examination of proposed intermediates in the reaction of 11 to form dication 12 using models and ab initio Hartree-Fock calculations using a 6-31G* basis set provides insight into this reaction. The calculations gave no indication of sulfurane formation.

Original languageEnglish (US)
Pages (from-to)273-291
Number of pages19
JournalJournal of Molecular Structure: THEOCHEM
Volume186
Issue numberC
DOIs
StatePublished - Apr 1989

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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