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Related Concept Videos

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.
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.
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...
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.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

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Related Experiment Video

Updated: Jun 1, 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,N-Bis(cyano-meth-yl)nitrous amide.

Yuan Zhang1, Meng Ting Han

  • 1Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China.

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

The study reveals how hydrogen bonds in a specific organic compound (C4H4N4O) create unique molecular structures. These interactions lead to the formation of dimers and chains, influencing the crystal packing.

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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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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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Hydrogen bonding is a crucial non-covalent interaction that dictates the assembly of molecules in the solid state.
  • Understanding crystal packing is essential for predicting and controlling the physical properties of organic compounds.

Purpose of the Study:

  • To investigate the role of hydrogen bonding in the self-assembly of the title compound, C4H4N4O.
  • To characterize the resulting supramolecular structures formed through intermolecular interactions.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the molecular structure and crystal packing.
  • Analysis of intermolecular interactions, specifically C-H⋯N hydrogen bonds, was performed.

Main Results:

  • Both hydrogen atoms of the methylene group in C4H4N4O participate in C-H⋯N hydrogen bonding.
  • These interactions lead to the formation of dimers arranged in R(2)(2)(12) motifs around inversion centers.
  • Further hydrogen bonding results in the formation of molecular chains extending along the c-axis.

Conclusions:

  • The specific arrangement of C-H⋯N hydrogen bonds in C4H4N4O governs its crystal structure.
  • The observed dimerization and chain formation highlight the directional nature of these interactions in directing supramolecular assembly.