Related Experiment Video
Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2-Chloro-5-(2-iodo-benzene-sulfonamido)-benzoic acid
Abstract:
In the mol-ecule of the title compound, C(13)H(9)ClINO(4)S, the coordination around the S atom is distorted tetra-hedral. The aromatic rings are oriented at a dihedral angle of 74.46 (9)°. Intra-molecular C-H⋯O hydrogen bonds result in the formation of two five- and one six-membered rings, which adopt planar, envelope and twisted conformations, respectively. In the crystal structure, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules to form R(2) (2)(8) ring motifs, which are further linked by C-H⋯O hydrogen bonds. π-π contacts between the benzene rings [centroid-centroid distances = 3.709 (3) and 3.772 (3) Å] may further stabilize the structure. The I atom is disordered over two positions, refined with occupancies of ca 0.75 and 0.25.
Related Concept Videos
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Reactions at the Benzylic Position: Halogenation
Nomenclature of Aromatic Compounds with Multiple Substituents
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Diazonium Group Substitution: –OH and –H

