X-Ray crystal structure and variable temperature NMR studies on N-arylhydroxamic acids

COLL 172

Ramanathan Natarajan, rnataraj@lakeheadu.ca1, Inderjit Nirdosh, inirdosh@lakeheadu.ca1, Alexandru Balaban, balabana@tamug.tamu.edu2, and Edmund Czerwinski, edcz@xray.utmb.edu3. (1) Department of Chemical Engineering, Lakehead University, 955 Oliver Road, Thunder Bay, ON P7B 5E1, Canada, (2) Marine Sciences Department, Texas A&M University at Galveston, 5007 Avenue U, Galveston, TX 77551, (3) Department of Biochemistry and Molecular Biology, University of Texas Medical Branch, Sealy Center for Structural Biology and Molecular Biophysics, Galveston, TX 77555-0647
The X-ray structures of several substituted N-arylhydroxamic acids R1-CO-N(R2)-OH showed that some have s-cis form and some have and s-trans form in the solid state. In the case of hydroxamic acids that were found to have s-cis form in the solid state, lowering the temperature of their CDCl3 solution did not result in splitting of NMR signals. By contrast, for those hydroxamic acids found to have s-trans form in the solid state, two sets of NMR peaks were observed when the temperature was lowered. From these experiments it was inferred that those with the s-cis form in the solid state have only that form even in CDCl3 solution.