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

doi:10.1016/S0022-2860(98)00711-X

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

Istituto Nazionale di Riposo e Cura per Anziani V.E. II

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	379-385
Number of pages	7
Journal	Journal of Molecular Structure
Volume	480-481
DOIs	https://doi.org/10.1016/S0022-2860(98)00711-X
Publication status	Published - 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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title = "FT-IR study of two [2-oxo-pyrrolidin-4-yl]carboxylate diastereomers in different solvent systems",

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.",

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

author = "P. Bruni and C. Conti and R. Galeazzi and A. Giardin{\`a} and E. Giorgini and E. Maurelli and G. Tosi",

year = "1999",

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T1 - FT-IR study of two [2-oxo-pyrrolidin-4-yl]carboxylate diastereomers in different solvent systems

AU - Bruni, P.

AU - Conti, C.

AU - Galeazzi, R.

AU - Giardinà, A.

AU - Giorgini, E.

AU - Maurelli, E.

AU - Tosi, G.

PY - 1999/5/4

Y1 - 1999/5/4

N2 - 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.

AB - 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.

KW - (3R)- and (3S)-1-[(R)-1-phenylethyl]-2-oxo-pyrrolidin-4-yl- carboxylate

KW - Hydrogen bonding

KW - Infrared spectra

KW - Molecular structure

KW - Solvent effect

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