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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.
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.
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.

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3,5-Dicarboxyanilinium nitrate dihydrate.

Wen-Xian Liang1, Yun-Ti Zhu

  • 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 study details the crystal structure of 5-ammonio-isophthalic acid nitrate dihydrate. Hydrogen bonds and π-π stacking interactions form a stable three-dimensional network in the crystal lattice.

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Area of Science:

  • Crystallography
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Understanding the crystal structure of organic salts is crucial for predicting their physical and chemical properties.
  • 5-ammonio-isophthalic acid is a key component in various chemical applications.
  • Nitrate salts often exhibit interesting structural and energetic characteristics.

Purpose of the Study:

  • To elucidate the crystal structure of 5-ammonio-isophthalic acid nitrate dihydrate.
  • To identify and analyze the intermolecular interactions governing the crystal packing.
  • To characterize the supramolecular architecture formed by the compound.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
  • Analysis of hydrogen bonding (N-H⋯O, O-H⋯O, C-H⋯O) was performed.
  • π-π stacking interactions were investigated using centroid-centroid distances.

Main Results:

  • The crystal structure consists of 5-ammonio-isophthalic acid cations, nitrate anions, and water molecules.
  • A robust three-dimensional network is formed through extensive hydrogen bonding.
  • Aromatic π-π stacking interactions, with centroid-centroid separations of 3.827(2) Å, further stabilize the structure.

Conclusions:

  • The crystal structure is characterized by a well-defined 3D network stabilized by both hydrogen bonds and π-π stacking.
  • The identified interactions provide insights into the solid-state behavior and potential applications of this compound.
  • This structural characterization contributes to the broader understanding of organic-inorganic hybrid materials.