The phenylsulfenium cation: Electronic structure and gas-phase reactivity

Authors
Bortolini, O Guerrini, A Lucchini, V Modena, G Pasquato, L
Citation
O. Bortolini et al., The phenylsulfenium cation: Electronic structure and gas-phase reactivity, TETRAHEDR L, 40(33), 1999, pp. 6073-6076
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
33
Year of publication
1999
Pages
6073 - 6076
Database
ISI
SICI code
0040-4039(19990813)40:33<6073:TPCESA>2.0.ZU;2-J
Abstract
The energies and the geometries of the phenylsulfenium cation (PhS+) in the singlet and triplet states have been optimized ab initio at the MP2/6-31G* /MP2/6-31G* level. The ((1)A) PhS+ state is more stable by 63.0 kJ mol(-1) than the ((3)A) PhS+ state. The PhS+ ion reacts in the gas-phase with ethyl ene and carbon monoxide affording the addition products [PhS+CO](+) and [Ph S+CH2CH2](+) respectively. Ab initio calculations and MS/MS spectra suggest that the additions of CH2CH2 and CO occur at the sulfur center. (C) 1999 E lsevier Science Ltd. All rights reserved.