TY - JOUR
T1 - Theoretical studies on transannular S-S interactions in geometrically constrained 1,5-dithiocane derivatives
AU - Glass, Richard S.
AU - Adamowicz, Ludwik
AU - Broeker, Jeffrey L.
N1 - Funding Information:
knowledge support of this work by the U.S. Public Health Service National Institutes of Health (Grant No. HL 15104).
PY - 1989/4
Y1 - 1989/4
N2 - 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.
AB - 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.
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U2 - 10.1016/0166-1280(89)87051-4
DO - 10.1016/0166-1280(89)87051-4
M3 - Article
AN - SCOPUS:45149144485
SN - 0166-1280
VL - 186
SP - 273
EP - 291
JO - Journal of Molecular Structure: THEOCHEM
JF - Journal of Molecular Structure: THEOCHEM
IS - C
ER -