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Related Concept Videos

Nitrosation of Enols01:19

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems01:15

Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems

Oxidative reactions are pivotal in metabolizing numerous compounds, including pharmaceutical drugs. These reactions often occur in carbon-heteroatom systems, such as carbon-nitrogen, carbon-sulfur, and carbon-oxygen.
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems01:19

Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems

Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...

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Related Experiment Video

Updated: May 27, 2026

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
07:38

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

Published on: September 25, 2017

N-(2-Nitro-oxyeth-yl)picolinamide.

Drielly A Paixão, Silvana Guilardi, Angelo de Fátima

    Acta Crystallographica. Section E, Structure Reports Online
    |November 9, 2011
    PubMed
    Summary

    This study reveals intramolecular hydrogen bonding within the C(8)H(9)N(3)O(4) molecule. The crystal structure shows these molecules forming chains through intermolecular interactions.

    Area of Science:

    • Crystallography
    • Molecular Chemistry

    Background:

    • Understanding molecular interactions is key in chemical research.
    • Intramolecular and intermolecular forces dictate crystal packing and properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the molecule C(8)H(9)N(3)O(4).
    • To identify and characterize hydrogen bonding interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular structure.
    • Analysis of intermolecular contacts was performed to understand crystal packing.

    Main Results:

    • The amide group participates in an intramolecular N-H⋯N hydrogen bond.
    • Molecules are arranged in chains along the a axis through weak intermolecular C-H⋯O interactions.

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    A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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    A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

    Published on: November 23, 2016

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    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
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    A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

    Published on: September 25, 2017

    A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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    A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

    Published on: January 21, 2020

    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
    11:01

    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

    Published on: November 23, 2016

    Conclusions:

    • The crystal structure of C(8)H(9)N(3)O(4) is characterized by specific hydrogen bonding patterns.
    • These interactions influence the overall supramolecular architecture in the solid state.