2012 Student Research Conference:
25th Annual Student Research Conference

Substituent Effects on C-H pKa and Bond Length in the Para Position of Benzene and the Potential of a Bipyridine Palladium Ligand System
Joshua B. Wilson
Dr. Eric V. Patterson, Faculty Mentor

The study of C-H bond reactivity is important in furthering our knowledge of organic materials, especially those rich in carbon-hydrogen bonds, such as petroleum and natural gas. The ability to cleave C-H bonds and replace hydrogen with a heteroatom under moderate conditions has yet to be refined. Aromatic C-H bonds are a particular challenge due to their high bond dissociation energies. In this study, the pKa and C-H bond lengths of the position para to varying substituent groups in benzene are determined via quantum mechanical calculations. Linear free energy relationships will help rationalize the effect of each substituent. The results from this study will be extrapolated to a bipyridine palladium ligand system, which further weakens the C-H bond and could form the basis for a practical catalytic system. Currently, transition state calculations are being performed to elucidate the mechanism in which the palladium ligand system will catalyze new carbon bonds.

Keywords: palladium, ligand, carbon, transition state, substituent groups, benzene, computational chemisty


Presentation Type: Oral Paper

Session: 310-3
Location: MG 2090
Time: 1:30

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