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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

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 water loss...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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.
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 Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.

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Related Experiment Video

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

3-Cyano-anilinium nitrate.

Bo Wang1

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

This study investigates the crystal structure of a nitrogen-containing compound. The findings reveal a planar arrangement of the nitrile and benzene groups, linked by hydrogen bonds into a 2D network.

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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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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Molecular structure

Background:

  • Understanding the packing of organic cations and anions in crystalline solids is crucial for predicting material properties.
  • Nitrogen-containing organic compounds exhibit diverse structural motifs and intermolecular interactions.
  • Benzene rings and nitrile groups are common functional groups in organic chemistry with distinct electronic and steric properties.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(7)H(7)N(2) (+)·NO(3) (-).
  • To analyze the molecular geometry and intermolecular interactions within the crystal lattice.
  • To characterize the hydrogen bonding network and its influence on the overall structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional arrangement of atoms.
  • Crystallographic data were analyzed to assess bond lengths, bond angles, and deviations from planarity.
  • Intermolecular interactions, specifically hydrogen bonding, were identified and characterized.

Main Results:

  • The cation, C(7)H(7)N(2) (+), and the nitrate anion, NO(3) (-), form an ionic compound.
  • The nitrile group and the benzene ring within the cation exhibit near-coplanarity, with a root-mean-square deviation of 0.006 Å.
  • Bifurcated N-H⋯(O,O) hydrogen bonds connect the ions, leading to the formation of a two-dimensional network parallel to the (001) crystallographic plane.

Conclusions:

  • The crystal structure is characterized by a well-defined two-dimensional hydrogen-bonded network.
  • The near-planarity of the cation's functional groups influences the packing and interactions in the solid state.
  • The study provides insights into the supramolecular assembly of organic salts driven by hydrogen bonding.