Molecular and crystalline structures of three (S)-4-alkoxycarbonyl-2- azetidinones containing long alkyl side chains from synchrotron X-ray powder diffraction data

Luis E. Seijas, Asiloé J. Mora, Gerzon E. Delgado, Francisco López-Carrasquero, María E. Báez, Michela Brunelli, Andrew N. Fitch

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

5 Citas (Scopus)

Resumen

The (S)-4-alkoxo-2-azetidinecarboxylic acids are optically active Β-lactam derivatives of aspartic acid, which are used as precursors of carbapenem-type antibiotics and poly-Β-aspartates. The crystal structures of three (S)-4-alkoxo-2-azetidinecarboxylic acids with alkyl chains with 10, 12 and 16 C atoms were solved using parallel tempering and refined against the X-ray powder diffraction data using the Rietveld method. The azetidinone rings in the three compounds display a pattern of asymmetrical bond distances and an almost planar conformation; these characteristics are compared with periodic solid-state, gas-phase density-functional theory (DFT) calculations and MOGUL average bond distances and angles from the CSD. The compounds pack along [001] as corrugated sheets separated by approximately 4.40 Å and connected by hydrogen bonds of the type N - H⋯O.

Idioma originalInglés estadounidense
Páginas (desde-hasta)724-730
Número de páginas7
PublicaciónActa Crystallographica Section B: Structural Science
Volumen65
N.º6
DOI
EstadoPublicada - 2009
Publicado de forma externa

Áreas temáticas de ASJC Scopus

  • Bioquímica, Genética y Biología Molecular General

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