Standard Article

Hydroxylamine, Oximate and Hydroxamate as α-Nucleophiles in Dephosphorylation

Hydroxylamines, Oximes and Hydroxamic Acids (2008)

  1. Erwin Buncel1,
  2. Ik Hwan Um2,
  3. François Terrier3

Published Online: 15 APR 2010

DOI: 10.1002/9780470682531.pat0469

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Buncel, E., Um, I. H. and Terrier, F. 2010. Hydroxylamine, Oximate and Hydroxamate as α-Nucleophiles in Dephosphorylation. Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    Queen's University, Department of Chemistry, Kingston, Ontario, Canada

  2. 2

    Ewha Womans University, Division of Nano Sciences and Department of Chemistry, Seoul, Korea

  3. 3

    Université de Versailles, Institut Lavoisier, Versailles Cedex, France

Publication History

  1. Published Online: 15 APR 2010

Abstract

  • 1
    Introduction
  • 2
    The α-Effect of Hydroxylamines, Oximes and Hydroxamic Acids
  • 3
    Ambident Nature of Hydroxylamines and Hydroxamates
  • 4
    Leveling Effect of α-Nucleophilicity: Brønsted-Type Plots
  • 5
    Solvent Effect on α-Nucleophilicity
  • 6
    Acetonitrile–Water Versus DMSO–Water Binary Mixtures
  • 7
    Imbalanced Transition State
  • 8
    Hydroxylamines, Hydroxamates and Oximates as Antidotes for Intoxication by Organophosphorus Toxins (Chemical Warfare Agents) and Organophosphorus Insecticides
  • 9
    Reactions of Oximate and Hydroxamate Nucleophiles in Surfactant Systems
  • 10
    Acknowledgment

Keywords:

  • hydroxylamine, oximate and hydroxamate as α-nucleophiles in dephosphorylation;
  • the α-effect of hydroxylamines, oximes and hydroxamic acids;
  • ambident nature of hydroxylamines and hydroxamates;
  • solvent effect on α-nucleophilicity;
  • acetonitrile–water versus DMSO–water binary mixtures;
  • imbalanced transition state;
  • mechanistic insight on oximate reactivity-provided by nature of Brønsted-type plots;
  • reactions of oximate and hydroxamate nucleophiles in surfactant systems

Featured Compounds

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  1. 1 - 31
Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:101.1039
Molecular Formula:C4H7NO2
InChIKey:FSEUPUDHEBLWJY-HWKANZROSA-N
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Compound 6
Molecular Weight:288.3007
Molecular Formula:C14H16N4O3
InChIKey:FJZDLOMCEPUCII-UHFFFAOYSA-P
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Compound 7
Molecular Weight:346.3799
Molecular Formula:C17H22N4O4
InChIKey:IBOONGYVIFFCDR-UHFFFAOYSA-P
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Compound 8
Molecular Weight:288.3007
Molecular Formula:C14H16N4O3
InChIKey:HIGRLDNHDGYWQJ-UHFFFAOYSA-P
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Compound 9
Molecular Weight:286.3279
Molecular Formula:C15H18N4O2
InChIKey:LJYGXPCCGGSATE-UHFFFAOYSA-P
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Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 4a
Molecular Weight:148.203
Molecular Formula:C5H10NO2S
InChIKey:IYJUCJGNFCSGMH-UHFFFAOYSA-O
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Compound 4b
Molecular Weight:149.168
Molecular Formula:C4H7NO3S
InChIKey:MQOUBTPCZPPIHX-GORDUTHDSA-N
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Compound 4c
Molecular Weight:133.169
Molecular Formula:C4H7NO2S
InChIKey:UJQBJDWFMFBDLF-GORDUTHDSA-N
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Compound 4d
Molecular Weight:87.0773
Molecular Formula:C3H5NO2
InChIKey:OVGLVOLWBBGQHS-DUXPYHPUSA-N
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Compound 4e
Molecular Weight:165.168
Molecular Formula:C4H7NO4S
InChIKey:GEKXLPLGSHHLAY-GORDUTHDSA-N
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Compound 5
Molecular Weight:287.3331
Molecular Formula:C16H19N2O3
InChIKey:CCBROZYLJDXSKJ-UHFFFAOYSA-O
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Compound 10
Molecular Weight:137.1592
Molecular Formula:C7H9N2O
InChIKey:JBKPUQTUERUYQE-UHFFFAOYSA-O
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Compound 11
Molecular Weight:246.3071
Molecular Formula:C13H18N4O
InChIKey:NRSXXHXAHVXZCY-UHFFFAOYSA-O
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Compound 12
Molecular Weight:137.1586
Molecular Formula:C7H9N2O
InChIKey:RYQHXWDFNMMYSD-UHFFFAOYSA-O
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Compound 13
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:ORIHZIZPTZTNCU-VMPITWQZSA-N
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Compound 15
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:OFYLBLSSPQTTHT-YVMONPNESA-N
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Compound 16
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:MTFJSAGADRTKCI-YVMONPNESA-N
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Compound 17
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:YBKOPFQCLSPTPV-YVMONPNESA-N
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Compound 18
Molecular Weight:113.0386
Molecular Formula:C2H2F3NO
InChIKey:AGXIAHLLNDREAE-BHQIHCQQSA-N
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Compound 19
Molecular Weight:189.1345
Molecular Formula:C8H6F3NO
InChIKey:TUKWYJVGKNCDJJ-GHXNOFRVSA-N
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Compound 20
Molecular Weight:181.0366
Molecular Formula:C3HF6NO
InChIKey:YVQTYCGUGOVSCD-UHFFFAOYSA-N
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Compound 21
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:JHNRZXQVBKRYKN-VQHVLOKHSA-N
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Compound 22
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 23
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 25
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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  1. 1 - 31