Nitrogen inversion and N-O bond rotation processes in di- and tri-substituted hydroxylamines. A dynamic NMR study

Sk Asrof Ali; Azfar Hassan; Mohammed I.M. Wazeer

doi:10.1039/P29960001479

Nitrogen inversion and N-O bond rotation processes in di- and tri-substituted hydroxylamines. A dynamic NMR study

Sk Asrof Ali^*
, Azfar Hassan
, Mohammed I.M. Wazeer

^*Corresponding author for this work

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

13 Scopus citations

Abstract

The barriers to inversion in several acyclic di- and tri-substituted hydroxylamines are determined by ¹H NMR band shape analysis. The barriers range from 49.1 to 66.8 kJ mol^-1 and are discussed in terms of a conformational process which involves nitrogen inversion and rotation around the N-O bond. The N-benzyl group with an ortho hydroxy substituent increases the nitrogen inversion barrier by 10 kJ mol^-1, which indicates the requirement of breaking of the intramolecular hydrogen bond prior to inversion.

Original language	English
Pages (from-to)	1479-1483
Number of pages	5
Journal	Journal of the Chemical Society. Perkin Transactions 2
Volume	7
DOIs	https://doi.org/10.1039/P29960001479
State	Published - 1996

ASJC Scopus subject areas

General Chemistry

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title = "Nitrogen inversion and N-O bond rotation processes in di- and tri-substituted hydroxylamines. A dynamic NMR study",

abstract = "The barriers to inversion in several acyclic di- and tri-substituted hydroxylamines are determined by 1H NMR band shape analysis. The barriers range from 49.1 to 66.8 kJ mol-1 and are discussed in terms of a conformational process which involves nitrogen inversion and rotation around the N-O bond. The N-benzyl group with an ortho hydroxy substituent increases the nitrogen inversion barrier by 10 kJ mol-1, which indicates the requirement of breaking of the intramolecular hydrogen bond prior to inversion.",

author = "Ali, \{Sk Asrof\} and Azfar Hassan and Wazeer, \{Mohammed I.M.\}",

year = "1996",

doi = "10.1039/P29960001479",

language = "English",

volume = "7",

pages = "1479--1483",

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

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T1 - Nitrogen inversion and N-O bond rotation processes in di- and tri-substituted hydroxylamines. A dynamic NMR study

AU - Ali, Sk Asrof

AU - Hassan, Azfar

AU - Wazeer, Mohammed I.M.

PY - 1996

Y1 - 1996

N2 - The barriers to inversion in several acyclic di- and tri-substituted hydroxylamines are determined by 1H NMR band shape analysis. The barriers range from 49.1 to 66.8 kJ mol-1 and are discussed in terms of a conformational process which involves nitrogen inversion and rotation around the N-O bond. The N-benzyl group with an ortho hydroxy substituent increases the nitrogen inversion barrier by 10 kJ mol-1, which indicates the requirement of breaking of the intramolecular hydrogen bond prior to inversion.

AB - The barriers to inversion in several acyclic di- and tri-substituted hydroxylamines are determined by 1H NMR band shape analysis. The barriers range from 49.1 to 66.8 kJ mol-1 and are discussed in terms of a conformational process which involves nitrogen inversion and rotation around the N-O bond. The N-benzyl group with an ortho hydroxy substituent increases the nitrogen inversion barrier by 10 kJ mol-1, which indicates the requirement of breaking of the intramolecular hydrogen bond prior to inversion.

UR - https://www.scopus.com/pages/publications/36949034428

U2 - 10.1039/P29960001479

DO - 10.1039/P29960001479

M3 - Article

AN - SCOPUS:36949034428

SN - 0300-9580

VL - 7

SP - 1479

EP - 1483

JO - Journal of the Chemical Society. Perkin Transactions 2

JF - Journal of the Chemical Society. Perkin Transactions 2

ER -

Nitrogen inversion and N-O bond rotation processes in di- and tri-substituted hydroxylamines. A dynamic NMR study

Abstract

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