Monte Carlo MM3(96) conformational analysis and X-ray crystal analysis of N,N'-dimethylxylaramide as a mimic for xylaric acid derived polyhydroxypolyamides (PHPAs)

CARB 84

Michael R. Hinton, Michael.Hinton@umontana.edu1, Michael K. Dowd, mkdowd@nola.srrc.usda.gov2, Brian Nicholson, b.nicholson@waikato.ac.nz3, and Donald E. Kiely, donkiely@selway.umt.edu1. (1) Shafizadeh Rocky Mountain Center for Wood and Carbohydrate Chemistry, Department of Chemistry, University of Montana, Missoula, MT 59801, (2) Southern Regional Research Center, U. S. Department of Agriculture, 1100 Robt. E. Lee Blvd, New Orleans, LA 70124, (3) Department of Chemistry, University of Waikato, Hamilton, New Zealand
Efforts to understand the conformational characteristics of the aldaryl monomer units of polyhydroxypolyamides (PHPAs) stems from our interest in correlating the conformations of these polymers with their properties and potential applications. To this end Monte Carlo MM3(96) conformational analyses of N,N'-dimethylxylaramide as a PHPA mimic were employed at several dielectric constants. Modeling results allowed comparison of calculated theoretical 1H vicinal coupling constants with experimental values obtained in different NMR solvents. Dominant low energy sickle conformations were in agreement with predicted steric relief from 1,3-dihydroxyl interactions, and a low energy extended conformation was in concert with the x-ray crystal structure.

 

General Posters
6:00 PM-8:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Carbohydrate Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007