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.
ASJC Scopus subject areas
- Condensed Matter Physics
- Physical and Theoretical Chemistry