Spectroscopic characterization of the 1-substituted 3,3-diphenyl-4-(2'-hydroxyphenyl)azetidin-2-ones: Application of C-13 NMR, H-1-C-13 COSYNMR and mass spectroscopy
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Publication Details
Author list: Singh GS, Pheko T
Publisher: Elsevier
Place: OXFORD
Publication year: 2008
Journal: Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (1386-1425)
Journal acronym: SPECTROCHIM ACTA A
Volume number: 70
Issue number: 3
Start page: 595
End page: 600
Number of pages: 6
ISSN: 1386-1425
Languages: English-Great Britain (EN-GB)
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Abstract
The article deals with spectroscopic characterization of azetidin-2-ones. The presence of substituents like hydroxyl, fluoro, methoxy and benzhydryl, etc., on the azetidin-2-one ring significantly affects the IR absorption and C-13 NMR frequencies of the carbonyl group present in these compounds. The presence of an ester carbonyl group or too many methine protons in the molecule has been observed to limit the scope of IR and H-1 NMR spectroscopy in unambiguous assignment of the structure. The application of C-13 NMR, 2D NMR (H-1-C-13 COSY) and mass spectroscopy in characterization of complex azetidin-2-ones is discussed. An application of the latter two techniques is described in deciding unequivocally between an azetidin-2-one ring and chroman-2-one ring structure for the product obtained by treatment of the 1-substituted 3,3-diphenyl-4-[2'-(O-diphenylacyl)hydroxyphenyl]-2-azetidinones with ethanolic sodium hydroxide at room temperature. (C) 2007 Elsevier B.V. All rights reserved.
Keywords
2D NMR, azetidin-2-ones, C-13 NMR, chroman-2-ones, H-1 NMR, IR, mass spectroscopy
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