David Yaffee
Project Title:

Examining the Oxidative Mechanisms of Alkene Substrates Catalyzed by a Dinuclear Iron Complex.

Contact Info:

tel: (617) 358-0292

email: dyaffee@bu.edu

Current Degree:

B.A./M.A. - Honors Chemistry - Boston University

Research Project:

My research involves the study of the reactivity of the dinuclear iron complex, Fe22+(HBamb)2(NMI)(DMF)2, developed by the Caradonna Lab. This system has been shown to catalyze the oxidation of simple alkanes, alkenes, and arenes utilizing oxygen atom sources such as iodosyl benzene. More recently, reactivity studies have been performed in the lab using 2-methyl-1-phenyl-2-propyl hydroperoxide (MPPH) as a mechanistic probe and oxygen atom source, and have demonstrated that the model system catalyzes O-O bond cleavage of peroxides following a radical free pathway, consistant with biological enzymes. My research to date has been to work out the conditions necessary for reproducible oxidation reactions using cyclohexane as a positive control reaction. Oxidations have yielded product with yields of up to 1400 turnovers but the results have as yet not been consistant.

Future work will revolve around the study of the mechanisms of simple alkenes and aromatics. By observing the products of oxidation of simple alkenes, the mechanistic details of epoxide formation can be established for the system of basic substrates. Along with a series of basic alkenes, the oxidation of toluene will be studied. The NIH shift mechanism of oxidation has been shown to occur in nature by enzymes such as phenylalanine hydroxylase (PAH). Once it has been shown that our system can oxidize toluene, selective sites on the aromatic ring can be deuterated, enabling the detection of the NIH shift mechanism.


Office of Resident's Life Certificate of Achievement for Exemplary Academic Performace while Serving as a Member of the Residence Life Staff (2002-2003)

CAS Dean's List (2001-2003)

Honors Program Graduate (2002)

Undergraduate Research Opportunities Program Summer Research Award (2003)

National Society of Collegiate Scholars (NSCS)

Golden Key International Honor's Society