DEUTERIUM KINETIC ISOTOPE EFFECT ON QUATERNIZATION OF N,N-DIMETHYLANILINE

Authors
RUDZINSKI J TADROS N PANETH P
Citation
J. Rudzinski et al., DEUTERIUM KINETIC ISOTOPE EFFECT ON QUATERNIZATION OF N,N-DIMETHYLANILINE, Journal of molecular structure, 321(1-2), 1994, pp. 97-99
Citations number
17
Categorie Soggetti
Chemistry Physical
Journal title
Journal of molecular structure → ACNP
ISSN journal
00222860
Volume
321
Issue
1-2
Year of publication
1994
Pages
97 - 99
Database
ISI
SICI code
0022-2860(1994)321:1-2<97:DKIEOQ>2.0.ZU;2-E
Abstract
The secondary, kinetic alpha-deuterium isotope effect for the quaterni zation of N,N-dimethylaniline by methyl iodide has been determined to be 0.968 +/- 0.004 at 25-degrees-C in ethanol. The size of this isotop e effect indicates that the transition state occurs earlier than in th e case of the p-CH3 analog (toluidine). This result is opposite to wha t is expected on the basis of reactivity-selectivity rules.