Correlation of rates of solvolysis of allyl chloroformate

CHED 804

Abigail Greenwood, babigal425@aim.com1, Stacey Mlynarski, stacey.mlynarski@students.wesley.edu1, Malcolm J. D'Souza, dsouzama@wesley.edu1, and Dennis N. Kevill, dkevill@niu.edu2. (1) Department of Chemistry, Wesley College, 120 N State Street, Dover, DE 19901, (2) Department of Chemistry & Biochemistry, Northern Illinois University, DeKalb, IL 60115
Allyl and vinyl chloroformates are often used in the synthesis of novel pro-drugs that are activated by the organism by means of natural biochemical processes. As a result there has been significant interest in their hydrolysis, alcoholysis, and aminolysis processes, as such reactions are useful models for enzymatic mechanisms. Hence, the effects of solvent variation of the available specific rates of solvolysis of allyl chloroformate are analyzed in terms of the extended Grunwald-Winstein equation using the NT scale of solvent nucleophilicity (based on solvolysis of S-methyldibenzothiophenium ion) combined with a YCl scale based on 1-adamantyl chloride solvolysis.
 

Undergraduate Research Poster Session: Biochemistry
2:00 PM-4:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008