Conformational assignments and a nitrogen inversion process in some 3-acyloxy-1,3-oxazinanes by NMR and X-ray analysis

Syed M.A. Hashmi; Mohammed I.M. Wazeer; M. Sakhawat Hussain; Joseph H. Reibenspies; Herman P. Perzanowski; Sk Asrof Ali

doi:10.1039/a807273f

Conformational assignments and a nitrogen inversion process in some 3-acyloxy-1,3-oxazinanes by NMR and X-ray analysis

Syed M.A. Hashmi
, Mohammed I.M. Wazeer
, M. Sakhawat Hussain
, Joseph H. Reibenspies
, Herman P. Perzanowski
, Sk Asrof Ali^*

^*Corresponding author for this work

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

5 Scopus citations

Abstract

The stereochemistry of the preferred conformers of several 3-acyloxy-1,3-oxazinanes has been established by NMR spectroscopy. A strong anomeric effect stabilizes the conformation having an equatorial orientation of the lone pair on nitrogen. A nitrogen inversion process was found to be the rate-limiting process in the conformational equilibria. The range of ΔG^‡ values was found to be 60-71 kJ mol^-1. Solid state structures as determined by X-ray diffraction confirm the findings of the NMR study.

Original language	English
Pages (from-to)	877-883
Number of pages	7
Journal	Journal of the Chemical Society. Perkin Transactions 2
Issue number	4
DOIs	https://doi.org/10.1039/a807273f
State	Published - Apr 1999

ASJC Scopus subject areas

General Chemistry

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title = "Conformational assignments and a nitrogen inversion process in some 3-acyloxy-1,3-oxazinanes by NMR and X-ray analysis",

abstract = "The stereochemistry of the preferred conformers of several 3-acyloxy-1,3-oxazinanes has been established by NMR spectroscopy. A strong anomeric effect stabilizes the conformation having an equatorial orientation of the lone pair on nitrogen. A nitrogen inversion process was found to be the rate-limiting process in the conformational equilibria. The range of ΔG‡ values was found to be 60-71 kJ mol-1. Solid state structures as determined by X-ray diffraction confirm the findings of the NMR study.",

author = "Hashmi, \{Syed M.A.\} and Wazeer, \{Mohammed I.M.\} and Hussain, \{M. Sakhawat\} and Reibenspies, \{Joseph H.\} and Perzanowski, \{Herman P.\} and Ali, \{Sk Asrof\}",

year = "1999",

month = apr,

doi = "10.1039/a807273f",

language = "English",

pages = "877--883",

journal = "Journal of the Chemical Society. Perkin Transactions 2",

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T1 - Conformational assignments and a nitrogen inversion process in some 3-acyloxy-1,3-oxazinanes by NMR and X-ray analysis

AU - Hashmi, Syed M.A.

AU - Wazeer, Mohammed I.M.

AU - Hussain, M. Sakhawat

AU - Reibenspies, Joseph H.

AU - Perzanowski, Herman P.

AU - Ali, Sk Asrof

PY - 1999/4

Y1 - 1999/4

N2 - The stereochemistry of the preferred conformers of several 3-acyloxy-1,3-oxazinanes has been established by NMR spectroscopy. A strong anomeric effect stabilizes the conformation having an equatorial orientation of the lone pair on nitrogen. A nitrogen inversion process was found to be the rate-limiting process in the conformational equilibria. The range of ΔG‡ values was found to be 60-71 kJ mol-1. Solid state structures as determined by X-ray diffraction confirm the findings of the NMR study.

AB - The stereochemistry of the preferred conformers of several 3-acyloxy-1,3-oxazinanes has been established by NMR spectroscopy. A strong anomeric effect stabilizes the conformation having an equatorial orientation of the lone pair on nitrogen. A nitrogen inversion process was found to be the rate-limiting process in the conformational equilibria. The range of ΔG‡ values was found to be 60-71 kJ mol-1. Solid state structures as determined by X-ray diffraction confirm the findings of the NMR study.

UR - https://www.scopus.com/pages/publications/0041626603

U2 - 10.1039/a807273f

DO - 10.1039/a807273f

M3 - Article

AN - SCOPUS:0041626603

SN - 0300-9580

SP - 877

EP - 883

JO - Journal of the Chemical Society. Perkin Transactions 2

JF - Journal of the Chemical Society. Perkin Transactions 2

IS - 4

ER -

Conformational assignments and a nitrogen inversion process in some 3-acyloxy-1,3-oxazinanes by NMR and X-ray analysis

Abstract

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