π-π Interaction in heterocyclic molecules

ORGN 825

Abhijit Mitra, abhijit.mitra@manhattan.edu1, Joseph F. Capitani1, Prantik Kundu, prantik@earthlink.net2, Christina Bergonzo, cbergonzo@gmail.com3, Libero Bartolotti, BARTOLOTTIL@ecu.edu4, and Pamela J. Seaton, seatonp@uncw.edu5. (1) Department of Chemistry and Biochemistry, Manhattan College/College of Mount St. Vincent, Riverdale, NY 10471, (2) Department of Chemistry and Biochemistry, Manhattan College/College of Mount St.Vincent, Riverdale, NY 10471, (3) Department of Chemistry and Biochemistry, Manhattan College/College of Mount Saint Vincent, Riverdale, NY 10471, (4) Department of Chemistry, East Carolina University, Greeneville, NC, (5) Department of Chemistry and Biochemistry, University of North Carolina, Wilmington, NC 28403
Non-covalent interactions play an important role in determining the properties and behaviors of biomolecules and their interaction with drugs and proteins. π-π Interaction is particularly prevalent in heterocyclic molecules such as quinoline. While many studies have involved dimers of benzene, fewer have involved dimers of heterocyclic molecules. Quinoline dimers have not been explored in spite of their prevalence in nature and pharmaceuticals. Benzene is the classic example, where it has been shown both experimentally and by ab initio calculations that the optimal geometry of such an interaction is T-shaped, in contrast to naphthalene where it is parallel. In this paper, we communicate the results of our studies on quinoline dimers by various methods including MP2 and DFT, with various basis sets and counterpoise corrections. Dimer geometries studied included "sandwich", "T-shaped," and "parallel displaced." The strategy utilized geometry optimizations and concomitant calculations of single point energies.
 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

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

Division of Organic Chemistry

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