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Study of the conversion of N-carbamoyl-L-proline to hydantoin-L-proline using powder synchrotron X-ray diffraction

Published online by Cambridge University Press:  29 February 2012

Luis E. Seijas ,
Asiloé J. Mora ,
Gerzon E. Delgado ,
Michela Brunelli  and
Andrew N. Fitch
Luis E. Seijas
Affiliation:
Laboratorio de Cristalografía, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida 5101, Venezuela
Asiloé J. Mora*
Affiliation:
Laboratorio de Cristalografía, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida 5101, Venezuela
Gerzon E. Delgado*
Affiliation:
Laboratorio de Cristalografía, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida 5101, Venezuela
Michela Brunelli
Affiliation:
Institut Laue Langevin, BP 156, F-38042 Grenoble Cedex, France
Andrew N. Fitch
Affiliation:
European Synchrotron Radiation Facility, BP 220, F-38043 Grenoble Cedex, France
*
a)Electronic mail: asiloe@ula.ve
b)Electronic mail: gerzon@ula.ve
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Abstract

The solvent-free conversion of N-carbamoyl-L-proline to hydantoin-L-proline by direct heating at 470 K is reported. A reaction mechanism is proposed based on a nucleophilic intramolecular substitution reaction involving both the lone pair of the NH2 group and the carboxylic acid group of the N-carbamoyl-L-proline. The DSC and TGA experiments show rising of the baselines of the curves prior to melting and decomposition given evidence of the onset of the thermal reaction. NMR experiments were used to identify the product of the reaction, hydantoin-L-proline, whose crystal structure was obtained from X-ray synchrotron powder diffraction data collected on the solidified melt. This compound displays a crystal packing directed by hydrogen bonds forming a layered structure pile up along the c direction.

Keywords

hydrogen bondinghydantoincrystal structureX-ray powder diffractionsynchrotron radiation
Type
Technical Articles
Information
Powder Diffraction , Volume 25 , Issue 4 , December 2010 , pp. 342 - 348
Copyright
Copyright © Cambridge University Press 2010

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