Crystal structure of cyclohexyl 4'-O-cyclohexyl-b-D-glucopyranosyl-(1→4)-b-D-glucopyranoside

CELL 183

Yuko Yoneda, yuko.yoneda@boku.ac.at1, Kurt Mereiter, Kurt.Mereiter@tuwien.ac.at2, Paul Kosma, paul.kosma@boku.ac.at1, Thomas Rosenau, thomas.rosenau@boku.ac.at1, and Alfred D. French, afrench@srrc.ars.usda.gov3. (1) Department of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A - 1190 Vienna, Austria, (2) Department of Chemistry, Vienna University of Technology, Getreidemarkt 9, A-1060 Vienna, Austria, (3) Southern Regional Research Center, New Orleans, LA 70124
The title compound was synthesized in seven steps in 16% overall yield starting from D-cellobiose, and was recrystallized from cyclohexane / methanol (v/v=1/1). There are three di-substituted cellobiose molecules and two cyclohexane molecules in the triclinic unit cell. Novel features include parallel and antiparallel packing as well as one of the O6 atoms residing in the tg orientation, seen in cellulose I but not previously in an analog. The structure is layered, with the cellobiose residues making an extensive network of intra- and intermolecular hydrogen bonds. The cyclohexyl groups and cyclohexane molecules sandwich the cellobiose residues, making a bread-meat-bread-bread-meat-bread structure. The quarter-stagger of adjacent molecules is similar to that in cellulose Ia, while the packing of the cellobiose units is somewhat similar in projection to that in cellulose III.
 

Structure and Properties of Cellulosic Polymers, Assemblies, and Nanocomposites
8:00 AM-11:45 AM, Tuesday, April 8, 2008 Morial Convention Center -- Rm. R07, Oral

Division of Cellulose & Renewable Materials

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