Organic chemistry, Biochemistry, Green chemistry, Pre-pharmacy advisor, American Chemical Society student chapter advisor
The Queen’s University of Belfast, Belfast, United Kingdom
Davidson College, Davidson, North Carolina, USA
CHEM 112 General Chemistry II
CHEM 211 Organic Chemistry I
CHEM 212 Organic Chemistry II
CHEM 240 Introduction to Biochemistry
CHEM 433 Advanced Organic Chemistry
CHEM 450 Senior Seminar
My research interests include the synthesis and characterization of novel ionic liquids (a.k.a. “molten salts”), catalysis, and biocatalysis. Current projects with students include:
Synthesis of long-chain (C12-C18) imidazolium ionic liquids (ILs) with an alkyne moiety incorporated mid-chain length. Prior research shows that incorporation of some functional groups into a long alkyl side chain, such as a cis double bond or a cyclopropane ring, can have large effects on the resulting IL’s physical and chemical properties–for example, dramatically lowering the melting point. The effect of an alkyne functional group has not previously been studied. We are synthesizing a group of related side chains with varying total chain length and position of the alkyne in the chain. The methods employed involve air-free synthesis techniques, so students gain experience in using a dual vacuum-inert gas manifold (a.k.a. Schlenk line, see below). After the ILs are synthesized, their physical (density, viscosity, thermal phase behavior, etc.) and chemical (reactivity in classic alkyne reactions) properties will be investigated.
A related project involves developing methods for biocatalytic synthesis of cyclopropanated long-chain fatty acid derivatives. Cyclopropane moieties, like cis double bonds, dramatically lower the melting point of a long-chain IL when incorporated into the side chain. However, they are resistant to oxidative degradation. Whereas the chemical synthesis of these structures involves somewhat hazardous chemical reagents, a greener synthesis may be possible using a tool from nature. Cyclopropane fatty acid synthase (CFA synthase) is a membrane-associated bacterial enzyme which performs the conversion of cis double bonds to cyclopropyl groups in the fatty acid side chains of phospholipid membranes in response to heat or oxidative stress. We are working in collaboration with Professor Felicia Etzkorn at Virginia Tech to develop an efficient way to harness the biocatalytic potential of CFA synthase to produce our desired structures. Since CFA synthase is only found to be active and stable in the presence of liposomes, we also work to develop direct and efficient syntheses of liposomes.
University of Ottawa, Ottawa, Ontario, Canada