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David Collum

Betty R. Miller Professor of Chemistry and Chemical Biology, Chemistry

Department Chair

Baker Laboratory, Room 482
dbc6@cornell.edu
607/255-4879

Educational Background

PhD, Columbia University, 1980
MPhil, Columbia University, 1980
MA, Columbia University, 1978
BS, Cornell University, 1977

Website(s)

Overview

The Collum group studies how aggregation and solvation dictate the reactivity and selectivity of organolithium compounds commonly used by synthetic chemists in both academia and the pharmaceutical industry. A combination of spectroscopic, kinetic, and computational methods bridge organic, organometallic, and analytical chemistry. 

Keywords

Physical organic chemistry, organolithium chemistry, kinetics and reaction mechanism

Departments/Programs

  • Chemistry and Chemical Biology

Graduate Fields

  • Chemistry and Chemical Biology

Research

The importance of organolithium reagents in organic chemistry is indisputable. Reports of the effects of solvents, reaction temperatures, additives, internal coordinating functionalities, electrophile structures, and substituents on product distributions pervade the literature. Nevertheless, complexities resulting from aggregation and solvation render our understanding of the origins of the reactivities and selectivities limited at best. Our group investigates the structural and mechanistic basis of selectivity using a range of spectroscopic, kinetic, and computational methods. A number of projects are in collaboration with pharmaceutical process groups.

Publications

Regioselective Lithium Diisopropylamide-Mediated Ortholithiation of 1-Chloro-3-(trifluoromethyl)benzene: Role of Autocatalysis, Lithium Chloride Catalysis, and Reversibility. Hoepker, A. C.; Gupta, L.; Ma, Y.; Faggin, M. F.; Collum, D. B. J. Am. Chem. Soc. 2011, 133, 7135.

 

Azaaldol Condensation of a Lithium Enolate Solvated by N,N,N’,N’ Tetramethylethylenediamine: Dimer-Based 1,2-Addition to Imines. De Vries, T. S.; Bruneau, A. M.; Liou, L. R.; Subramanian, H.; Collum, D. B. J. Am. Chem. Soc. 2013, 135, 4214.

 

Enediolate-Dilithium Amide Mixed Aggregates in the Enantioselective

Alkylation of Arylacetic Acids: Structural Studies and a Stereochemical Model. Ma, Y.; Stivala, C. E.; Wright, A. M.; Hayton, T.; Liang, J.; Keresztes, I.; Lobkovsky, E.; Collum, D. B.; Zakarian, Z. J. Am. Chem. Soc. 2013, 135, 16853.

 

Method of Continuous Variations: Applications of Job Plots to the Study of Molecular Associations in Organometallic Chemistry. Renny, J. S.; Tomasevich, L. L.; Tallmadge, E. H.; Collum, D. B. Angew. Chem., Int. Ed. 2013, 52, 11998.

 

Solution Structures of Lithium Amino Alkoxides Used in Highly Enantioselective 1,2-Additions. Bruneau, A. M.; Collum, D. B. J. Am. Chem. Soc. 2014, 53, 2885.

Current Courses

There are no current courses listed for this faculty member.