X-ray study of N-triphenylmethylformamide and computational study of triphenylmethylcyclohexane

ORGN 128

Eric A. Noe, ean12001@yahoo.com1, Frank R. Fronczek, ffroncz@lsu.edu2, Diwakar M Pawar, ean12001@yahoo.com1, and Dalephine Cain, ean12001@yahoo.com1. (1) Department of Chemistry, Jackson State University, 1400 J. R. Lynch Street, Jackson, MS 39217-0510, (2) Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804
An X-ray diffraction study of N-triphenylmethylformamide found the conformation to be E. Our earlier NMR study showed that the major conformation in solution is also E, in contrast to most acyclic secondary amides, which have a larger population of the Z. The preference for the E conformation is a consequence of the large size of the triphenylmethyl group. MM4 calculations for triphenylmethylcyclohexane indicate that the group is larger than tert-butyl, but not by as much as might be suggested by the A values of methyl and phenyl.
 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008