Related Experiment Video
Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
4-tert-Butyl-amino-3-nitro-benzoic acid
Abstract:
In the title compound, C(11)H(14)N(2)O(4), all non-H atoms lie in a mirror plane except for one of the methyl groups which deviates from the mirror plane by 0.919 (3) Å and is twisted by a torsion angle of 62.9 (2)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal packing, the mol-ecules are linked together by O-H⋯O hydrogen bonds, forming dimers with graph-set motif R(2) (2)(8) which propagate along the a-axis direction. C-H⋯O contacts link adjacent dimers with a graph-set motif C(2) (2)(7), forming chains along b, and further consolidate the structure into a three-dimensional network. The crystal packing is further strengthened by short inter-molecular O⋯O=C [2.655 (4) Å] contacts.
Related Concept Videos
Electrophilic Aromatic Substitution: Nitration of Benzene
2° Amines to N-Nitrosamines: Reaction with NaNO2
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...
NMR Spectroscopy of Benzene Derivatives
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Diazonium Group Substitution: –OH and –H

