2011 Student Research Conference:
24th Annual Student Research Conference

Substituent Effects on C-H pKa and Bond Length in the Para Position of Benzene
Josh B. Wilson
Dr. Eric V. Patterson, Faculty Mentor

The study of C-H bond reactivity is important in furthering our knowledge of all organic materials, especially those rich in carbon-hydrogen bonds, such as petroleum and natural gas. The ability to cleave a C-H bond and replace the 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.

Keywords: pKa, bond length, benzene, para, substituent, bipyridine palladium ligand system

Topic(s):Chemistry

Presentation Type: Oral Paper

Session: 43-6
Location: MG 1000
Time: 4:00

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