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Quantum chemical study of several monocyclic complex β‐lactam C‐3, C‐4, and N‐derivatives, and β‐ring model molecules
Author(s) -
Palafox Mauricio Alcolea,
Iza Nerea,
Gil Manuel,
Núñez José Luís
Publication year - 2002
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.10204
Subject(s) - chemistry , lactam , ring (chemistry) , amide , molecule , quantum chemical , stereochemistry , cyclobutane , planarity testing , computational chemistry , azetidine , resonance (particle physics) , crystallography , organic chemistry , physics , particle physics
A quantum chemical study of several complex monocyclic 4‐benzoyl‐4‐phenyl‐β‐lactam derivatives was carried out using cyclobutane, azetidine, 2‐azetidinone, 1‐methyl‐2‐azetidinone, and 3‐methyl‐2‐azetidinone as model compounds. The optimum geometry was obtained for the different conformations. The planarity of the ring was discussed in terms of the influence of the substituents on the amide resonance. To better analyze the amide resonance and the activity of the β‐lactam ring, a vibrational study was also carried out. To examine the influence of solvent polarity on the carbonyl bands, the Fourier transform–infrared (FT‐IR) spectra of the β‐lactam monocyclic derivatives were recorded in CCl 4 , C 6 H 6 , and CHCl 3 solutions. The normal vibrations of the β‐lactam ring in the model compounds were characterized and used in the analysis of the β‐ring of more complex derivatives. © 2002 Wiley Periodicals, Inc. Int J Quantum Chem, 2002