Spectroscopic characterization of the 1-substituted 3,3-diphenyl-4-(2′-hydroxyphenyl)azetidin-2-ones

Application of 13C NMR, 1H-13C COSY NMR and mass spectroscopy

Girija S. Singh, Tshepo Pheko

Research output: Contribution to journalArticle

8 Citations (Scopus)

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 13C 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 1H NMR spectroscopy in unambiguous assignment of the structure. The application of 13C NMR, 2D NMR (1H-13C 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.

Original languageEnglish
Pages (from-to)595-600
Number of pages6
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume70
Issue number3
DOIs
Publication statusPublished - Aug 1 2008

Fingerprint

mass spectroscopy
Nuclear magnetic resonance
Spectroscopy
nuclear magnetic resonance
Chromans
spectroscopy
Sodium Hydroxide
Hydroxyl Radical
Nuclear magnetic resonance spectroscopy
Protons
sodium hydroxides
rings
ring structures
Esters
Sodium
esters
Molecules
protons
diphenyl
room temperature

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

Cite this

@article{39fd375d5f0d41d5a01bf0e7e423779e,
title = "Spectroscopic characterization of the 1-substituted 3,3-diphenyl-4-(2′-hydroxyphenyl)azetidin-2-ones: Application of 13C NMR, 1H-13C COSY NMR and mass spectroscopy",
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 13C 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 1H NMR spectroscopy in unambiguous assignment of the structure. The application of 13C NMR, 2D NMR (1H-13C 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.",
author = "Singh, {Girija S.} and Tshepo Pheko",
year = "2008",
month = "8",
day = "1",
doi = "10.1016/j.saa.2007.08.003",
language = "English",
volume = "70",
pages = "595--600",
journal = "Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy",
issn = "1386-1425",
publisher = "Elsevier",
number = "3",

}

TY - JOUR

T1 - Spectroscopic characterization of the 1-substituted 3,3-diphenyl-4-(2′-hydroxyphenyl)azetidin-2-ones

T2 - Application of 13C NMR, 1H-13C COSY NMR and mass spectroscopy

AU - Singh, Girija S.

AU - Pheko, Tshepo

PY - 2008/8/1

Y1 - 2008/8/1

N2 - 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 13C 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 1H NMR spectroscopy in unambiguous assignment of the structure. The application of 13C NMR, 2D NMR (1H-13C 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.

AB - 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 13C 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 1H NMR spectroscopy in unambiguous assignment of the structure. The application of 13C NMR, 2D NMR (1H-13C 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.

UR - http://www.scopus.com/inward/record.url?scp=44649196424&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=44649196424&partnerID=8YFLogxK

U2 - 10.1016/j.saa.2007.08.003

DO - 10.1016/j.saa.2007.08.003

M3 - Article

VL - 70

SP - 595

EP - 600

JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

SN - 1386-1425

IS - 3

ER -