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

Luis E. Seijas, Asiloé J. Mora, Gerzon E. Delgado, Michela Brunelli, Andrew N. Fitch

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

13 Citas (Scopus)

Resumen

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.

Idioma originalInglés estadounidense
Páginas (desde-hasta)342-348
Número de páginas7
PublicaciónPowder Diffraction
Volumen25
N.º4
DOI
EstadoPublicada - 2010
Publicado de forma externa

Áreas temáticas de ASJC Scopus

  • Radiación
  • Ciencia de los Materiales General
  • Instrumental
  • Física de la materia condensada

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