Study of inversion isomerism in some 4,5-cis-substituted-2-isoxazolidineethanols by NMR spectroscopy

Shaikh A. Ali; Mohamed I.M. Wazeer

doi:10.1016/j.saa.2008.02.040

Study of inversion isomerism in some 4,5-cis-substituted-2-isoxazolidineethanols by NMR spectroscopy

Shaikh A. Ali^*
, Mohamed I.M. Wazeer

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

A series of β-phenyl-2-isoxazolidineethanols having cis-disposed substituents at C(4) and C(5) has been prepared by asymmetric nitrone cycloaddition reactions and their NMR spectra recorded over a wide range of temperatures. The spectra in CDCl₃ at low temperatures indicate the presence of two interconverting invertomers for some of the tri-substituted isoxazolidines. The effect of H-bonding - intramolecular in CDCl₃ and intermolecular in CD₃OD - on the population ratio of the nitrogen invertomers has been investigated. The nitrogen inversion barriers are determined using complete line-shape analysis, and their dependence on solvent is discussed.

Original language	English
Pages (from-to)	292-295
Number of pages	4
Journal	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume	71
Issue number	1
DOIs	https://doi.org/10.1016/j.saa.2008.02.040
State	Published - Nov 2008

Keywords

Inversion barriers
Invertomers
Isoxazoldines
Nitrogen inversion

ASJC Scopus subject areas

Analytical Chemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Spectroscopy

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10.1016/j.saa.2008.02.040

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title = "Study of inversion isomerism in some 4,5-cis-substituted-2-isoxazolidineethanols by NMR spectroscopy",

abstract = "A series of β-phenyl-2-isoxazolidineethanols having cis-disposed substituents at C(4) and C(5) has been prepared by asymmetric nitrone cycloaddition reactions and their NMR spectra recorded over a wide range of temperatures. The spectra in CDCl3 at low temperatures indicate the presence of two interconverting invertomers for some of the tri-substituted isoxazolidines. The effect of H-bonding - intramolecular in CDCl3 and intermolecular in CD3OD - on the population ratio of the nitrogen invertomers has been investigated. The nitrogen inversion barriers are determined using complete line-shape analysis, and their dependence on solvent is discussed.",

keywords = "Inversion barriers, Invertomers, Isoxazoldines, Nitrogen inversion",

author = "Ali, \{Shaikh A.\} and Wazeer, \{Mohamed I.M.\}",

year = "2008",

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doi = "10.1016/j.saa.2008.02.040",

language = "English",

volume = "71",

pages = "292--295",

journal = "Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy",

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number = "1",

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TY - JOUR

T1 - Study of inversion isomerism in some 4,5-cis-substituted-2-isoxazolidineethanols by NMR spectroscopy

AU - Ali, Shaikh A.

AU - Wazeer, Mohamed I.M.

PY - 2008/11

Y1 - 2008/11

N2 - A series of β-phenyl-2-isoxazolidineethanols having cis-disposed substituents at C(4) and C(5) has been prepared by asymmetric nitrone cycloaddition reactions and their NMR spectra recorded over a wide range of temperatures. The spectra in CDCl3 at low temperatures indicate the presence of two interconverting invertomers for some of the tri-substituted isoxazolidines. The effect of H-bonding - intramolecular in CDCl3 and intermolecular in CD3OD - on the population ratio of the nitrogen invertomers has been investigated. The nitrogen inversion barriers are determined using complete line-shape analysis, and their dependence on solvent is discussed.

AB - A series of β-phenyl-2-isoxazolidineethanols having cis-disposed substituents at C(4) and C(5) has been prepared by asymmetric nitrone cycloaddition reactions and their NMR spectra recorded over a wide range of temperatures. The spectra in CDCl3 at low temperatures indicate the presence of two interconverting invertomers for some of the tri-substituted isoxazolidines. The effect of H-bonding - intramolecular in CDCl3 and intermolecular in CD3OD - on the population ratio of the nitrogen invertomers has been investigated. The nitrogen inversion barriers are determined using complete line-shape analysis, and their dependence on solvent is discussed.

KW - Inversion barriers

KW - Invertomers

KW - Isoxazoldines

KW - Nitrogen inversion

UR - https://www.scopus.com/pages/publications/49849099536

U2 - 10.1016/j.saa.2008.02.040

DO - 10.1016/j.saa.2008.02.040

M3 - Article

C2 - 18407787

AN - SCOPUS:49849099536

SN - 1386-1425

VL - 71

SP - 292

EP - 295

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

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

IS - 1

ER -

Study of inversion isomerism in some 4,5-cis-substituted-2-isoxazolidineethanols by NMR spectroscopy

Abstract

Keywords

ASJC Scopus subject areas

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