A Semiempirical Transition State Structure for the First Step in the Alkaline Hydrolysis of Cocaine. Comparison between the Transition State Structure, the Phosphonate Monoester Transition State Analog, and a Newly Designed Thiophosphonate Transition State Analog

Authors

George C. Shields, Bucknell UniversityFollow
Edward C. Sherer
Gordon M. Turner
Tricia N. Lively
Donald W. Landry

Publication Date

1996

Description

Semiempirical molecular orbital calculations have been performed for the first step in the alkaline hydrolysis of the neutral benzoylester of cocaine. Successes, failures, and limitations of these calculations are reviewed. A PM3 calculated transition state structure is compared with the PM3 calculated structure for the hapten used to induce catalytic antibodies for the hydrolysis of cocaine. Implications of these calculations for the computer–aided design of transition state analogs for the induction of catalytic antibodies are discussed.

Journal

Journal of Molecular Modeling

Volume

2

First Page

62

Last Page

69

Department

Chemistry

Link to Published Version

http://www.springerlink.com/content/dpvbf7bh4rh5p7u6/

Recommended Citation

Shields, George C.; Sherer, Edward C.; Turner, Gordon M.; Lively, Tricia N.; and Landry, Donald W.. "A Semiempirical Transition State Structure for the First Step in the Alkaline Hydrolysis of Cocaine. Comparison between the Transition State Structure, the Phosphonate Monoester Transition State Analog, and a Newly Designed Thiophosphonate Transition State Analog." Journal of Molecular Modeling (1996) : 62-69.