Related Experiment Video
Updated: May 15, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
N,N-Diethyl-2-(4-methyl-benzene-sulfonamido)-benzamide
Maria Altamura1, Valentina Fedi, Rossano Nannicini
1Chemistry Department, Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy.
Abstract:
The asymmetric unit of the title compound, C(18)H(22)N(2)O(3)S, contains two mol-ecules, exhibiting similar conformations [C-S-N-C torsion angles of -82.2 (2) and -70.4 (2)°, and dihedral angles between the mean planes of the aromatic rings of 56.6 (6) and 51.6 (6)° in mol-ecules I and II, respectively]. However, the two independent mol-ecules show distinctly different hydrogen-bonding patterns. In the crystal, molecules I form inversion dimers via pairs of N-H⋯O hydrogen bonds, whereas for molecules II the N-H⋯O hydrogen bond is intramolecular. The hydrogen-bonded dimers of I further propagate along the b-axis direction through π-π inter-actions [the distance between ring centroids is 3.8424 (8) Å].
Related Concept Videos
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Diazonium Group Substitution: –OH and –H
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...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Electrophilic Aromatic Substitution: Nitration of Benzene

