FT-IR study of two [2-oxo-pyrrolidin-4-yl]carboxylate diastereomers in different solvent systems

P. Bruni, C. Conti, R. Galeazzi, A. Giardinà, E. Giorgini, E. Maurelli, G. Tosi

Research output: Contribution to journalArticlepeer-review

Abstract

The infrared study of the solvent effect on two diasteroisomeric (3R)- and (3S)-1-[(R)-1-phenylethyl]-2-oxo-pyrrolidin-4-ylcarboxylates (A and B) acting as homo-β-proline inhibitory neurotransmitter precursors, is reported. Apart from the slight red shift of the carbonyl bands of A, the interactions of the title compounds with the solvents are comparable. In hydroxylic solvents, the solutes are hosts in intermolecularly H-bonded alcohol clusters, the percentage of specific solute-solvent interaction being higher for compound A. This result confirms theoretical findings and X-ray diffraction studies.

Original languageEnglish
Pages (from-to)379-385
Number of pages7
JournalJournal of Molecular Structure
Volume480-481
DOIs
Publication statusPublished - May 4 1999

Keywords

  • (3R)- and (3S)-1-[(R)-1-phenylethyl]-2-oxo-pyrrolidin-4-yl- carboxylate
  • Hydrogen bonding
  • Infrared spectra
  • Molecular structure
  • Solvent effect

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

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