SUBSTITUENT EFFECTS ON THE KINETIC SOLVENT ISOTOPE EFFECT IN SOLVOLYSES OF ARENESULFONYL CHLORIDES

Authors
KOO IS LEE I OH J YANG K BENTLEY TW
Citation
Is. Koo et al., SUBSTITUENT EFFECTS ON THE KINETIC SOLVENT ISOTOPE EFFECT IN SOLVOLYSES OF ARENESULFONYL CHLORIDES, Journal of physical organic chemistry, 6(4), 1993, pp. 223-227
Citations number
24
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Journal of physical organic chemistry → ACNP
ISSN journal
08943230
Volume
6
Issue
4
Year of publication
1993
Pages
223 - 227
Database
ISI
SICI code
0894-3230(1993)6:4<223:SEOTKS>2.0.ZU;2-1
Abstract
The Hammett type plot of kinetic solvent isotope effect (KSIE = k(SOH) /k(SOD)), log(KSIE) vs sigma, can be a useful mechanistic tool for sol volytic reactions. The slopes of such straight line plots for para-sub stituted benzenesulphonyl chlorides in methanol (0.15), water (0.05) a nd methanol-water (0-05) are interpreted in terms of different reactio n channels (general base-catalysed and S(N)2), in contrast to simple H ammett plots, log k(SOH) (or log K(SOD)) VS sigma, invariably exhibiti ng non-linear concave curves.