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

Research output: Contribution to journalResearch Articlepeer-review

13 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)342-348
Number of pages7
JournalPowder Diffraction
Volume25
Issue number4
DOIs
StatePublished - 2010
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Radiation
  • General Materials Science
  • Instrumentation
  • Condensed Matter Physics

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