STRUCTURE-STABILITY RELATIONSHIPS IN UNSATURATED SULFUR-COMPOUNDS - VI - AN AB-INITIO STUDY OF THE STABLE CONFORMATIONS OF (E)-2-METHYLTHIO-2-BUTENES, (E)-2-METHYLSULFINYL-2-BUTENES, (E)2-METHYLSULFONYL-2-BUTENES, (Z)-2-METHYLTHIO-2-BUTENES, (Z)-2-METHYLSULFINYL-2-BUTENES AND (Z)-2-METHYLSULFONYL-2-BUTENES

Citation
R. Kimmelma et M. Hotokka, STRUCTURE-STABILITY RELATIONSHIPS IN UNSATURATED SULFUR-COMPOUNDS - VI - AN AB-INITIO STUDY OF THE STABLE CONFORMATIONS OF (E)-2-METHYLTHIO-2-BUTENES, (E)-2-METHYLSULFINYL-2-BUTENES, (E)2-METHYLSULFONYL-2-BUTENES, (Z)-2-METHYLTHIO-2-BUTENES, (Z)-2-METHYLSULFINYL-2-BUTENES AND (Z)-2-METHYLSULFONYL-2-BUTENES, Journal of molecular structure. Theochem, 418(2-3), 1997, pp. 189-196
Citations number
29
Language
INGLESE
art.tipo
Article
ISSN journal
0166-1280
Volume
418
Issue
2-3
Year of publication
1997
Pages
189 - 196
Database
ISI
SICI code
0166-1280(1997)418:2-3<189:SRIUS->2.0.ZU;2-L
Abstract
The potential energy curves for the C-S torsion of (E)- and (Z)-2-meth ylthio-, methylsulfinyl-and methylsulfonyl-2-butenes were calculated u sing ab initio methods (RHF/3-21G and 6-31G*). Each molecule had two energy minima symmetrically (ca. 60 degrees) of the s-trans (antiperip lanar) conformation. (E)-2-methylthio-2-butene also had a third local minimum in the s-cis (synperiplanar) conformation. In 2-methylthio-2-b utene the Z isomer had ca. 2 kJ mol(-1) lower energy than the E isomer . In the other two compounds the E isomer was the more stable one. The energy difference between the geometric isomers in 2-methylsulfinyl- and 2-methylsulfonyl-2-butene was 6-8 and 11-14 kT mol(-1), respective ly. (C) 1997 Elsevier Science B.V.