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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 12, Number 1
BKCSDE 12(1)
January 20, 1991 

Kinetic Isotope Effects Involving Deuterated Benzylamine Nucleophiles
Ikchoon Lee*, Han Joong Koh, Dong Sook Sohn, Byung Choon Lee
The kinetic isotope effects (KIE) are determined for the reactions of benzyl benzenesulfonates (BBS), ethyl benzenesulfonates (EBS) and phenacyl benzensulfonates (PAB) with deuterated benzylamine nucleophiles. The inverse secondary α-deuterium KIE observed were somewhat smaller than those for the corresponding reactions with aniline nucleophiles. The primary KIEs obtained with PAB were slightly greater than those for the corresponding reactions with anilines, which suggested that the inverse secondary KIE is decreased due to a relatively earlier transition state for bond-making with little change in the hydrogen bonding strength to the carbonyl oxygen.
101 - 103
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