Conformational polymorphism in meta-substituted diphenyl ureas

ANYL 50

Shoaleh Dehghan, sd268@georgetown.edu, Christina A. Capacci, cac66@georgetown.edu, Rupa Hiremath, rh7@georgetown.edu, and Jennifer A. Swift, jas2@georgetown.edu. Department of Chemistry, Georgetown University, 37th and O Streets NW, Washington, DC 20057
Crystal polymorphism, the formation of different crystal structures from the same molecules, is a major unsolved problem in solid-state chemistry and pharmaceutical manufacturing. Meta-substituted diphenyl ureas (MXPU) with X=Cl, Br, I, CN, NO2, CH3, and OH can adopt different conformations in different solid state packing arrangements, a phenomena called conformational polymorphism. We have recently determined the single crystal growth conditions and X-ray structure solutions of many of these meta-substituted compounds. Ab initio calculations were also performed for a series of symmetrical and unsymmetrical MXPUs. Potential energy scans for the rotation of either one or both phenyl rings show some regions of low conformational energy which correspond to anti-anti < anti-syn < syn-syn in all of the compounds except when X= CH3 or OH. In these cases syn isomers are more stable. Comparisons are made between the calculated torsion angles and those observed in the crystalline solid state.
 

General Papers
7:00 PM-9:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Analytical Chemistry

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