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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.0K
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,...
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
4.0K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.5K
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.
4.5K
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

5.8K
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
5.8K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.4K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.4K
Preparation of Amides01:29

Preparation of Amides

3.2K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.2K

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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Pyridine-4-carboxamidoxime N-oxide.

Clifford W Padgett1, Kirkland Sheriff1, Will E Lynch1

  • 1Georgia Southern University, 11935 Abercorn St., Department of Chemistry and Biochemistry, Savannah GA 31419, USA.

Iucrdata
|November 7, 2022
PubMed
Summary

We report the first crystal structure of pyridine-4-carboxamidoxime N-oxide, a compound synthesized during metal-organic framework research. This molecule forms layered structures through specific hydrogen bonding interactions.

Keywords:
N-oxidecrystal structurehydrogen bondingoximesupra­molecular structure

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Area of Science:

  • Materials Science
  • Crystallography
  • Organic Chemistry

Background:

  • Metal-organic frameworks (MOFs) are synthesized using organic N-oxides.
  • Pyridine-4-carboxamidoxime N-oxide is a novel compound within this research area.

Purpose of the Study:

  • To determine the crystal structure of pyridine-4-carboxamidoxime N-oxide.
  • To analyze the intermolecular interactions and crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the crystal structure.
  • Analysis of hydrogen bonding and molecular geometry was performed.

Main Results:

  • The first crystal structure of pyridine-4-carboxamidoxime N-oxide (C6H7N3O2) is reported.
  • The hydroxy-carbamimidoyl group is nearly coplanar with the pyridine ring.
  • The compound forms hydrogen-bonding layers stabilized by O-H⋯O and N-H⋯O interactions, creating R34(24) ring motifs.
  • No π-π interactions were observed in the crystal structure.

Conclusions:

  • The crystal structure reveals specific hydrogen bonding patterns essential for layer formation.
  • This study provides fundamental structural insights into pyridine-4-carboxamidoxime N-oxide relevant to MOF synthesis.