STERIC EFFECTS IN S(N)2 REACTIONS - PRIMARY CARBON KINETIC ISOTOPE EFFECTS IN MENSHUTKIN REACTIONS

Authors
PERSSON J BERG U MATSSON O
Citation
J. Persson et al., STERIC EFFECTS IN S(N)2 REACTIONS - PRIMARY CARBON KINETIC ISOTOPE EFFECTS IN MENSHUTKIN REACTIONS, Journal of organic chemistry, 60(16), 1995, pp. 5037-5040
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
16
Year of publication
1995
Pages
5037 - 5040
Database
ISI
SICI code
0022-3263(1995)60:16<5037:SEISR->2.0.ZU;2-3
Abstract
The C-11/C-14 kinetic isotope effect (KIE) has been used to probe ster ic hindrance in the Menshutkin reactions of different substituted amin es with labeled methyl iodide. The KIEs for the reaction of 2,6-lutidi ne and 2,4-lutidine with labeled methyl iodide in acetonitrile were de termined to 1.220 +/- 0.009 and 1.189 +/- 0.012, respectively. The C-1 1/C-14 KIEs for the reaction of triethylamine and quinuclidine, with l abeled methyl iodide in 1,2-dimethoxyethane were determined to 1.221 /- 0.006 and 1.220 +/- 0.005, respectively.