Related Experiment Video
Updated: Jun 1, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
2-(2,4-Dinitro-benz-yl)pyridinium 2-hy-droxy-3,5-dinitro-benzoate
Abstract:
In the structure of the title salt, C(12)H(10)N(3)O(4) (+)·C(7)H(3)N(2)O(7) (-), the cations and the anions are linked by a single N(+)-H⋯O(carbox-yl) hydrogen bond, the discrete cation-anion unit having no inter-molecular associations other than weak cation-anion aromatic ring π-π inter-actions [ring centroid separation = 3.7320 (14) Å] and a number of weak inter-unit aromatic C-H⋯O contacts. An intramolecular C-H⋯O hydrox-yl-carboxyl hydrogen bond occurs in the anion.
Related Concept Videos
Diazonium Group Substitution: –OH and –H
Hydrolysis of Chlorobenzene to Phenol: Dow Process
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
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...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
Electrophilic Aromatic Substitution: Nitration of Benzene

