Quantum chemical studies of a carbon acid catalyst in Friedel-Crafts acylation reactions

PHYS 576

Katie R. Mitchell-Koch, mitchkt@ku.edu, Mikhail V. Barybin, mbarybin@ku.edu, and Ward H. Thompson, wthompson@ku.edu. Department of Chemistry, University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, KS 66045
A computational study of the carbon acid-catalyzed selective acylation of 2-methoxynaphthalene (2-MON) to form 2-acetyl-6-methoxynaphthalene (2,6-AMN) is presented. The 2,6-AMN product, a precursor of the anti-inflammatory drug (S)-Naproxen, is difficult to obtain through Friedel-Crafts catalysis. In this work, density functional theory calculations are used to investigate the selectivity and mechanism of the Friedel-Crafts acylation of 2-MON by pentafluorophenylbis(triflyl)methane to yield 2,6-AMN. Computed free energies are compared to experimental yields to rationalize regioselectivity. Potential reaction pathways are discussed, and the effect of chemical modifications on the catalyst is explored.

Poster Session
7:30 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Physical Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006