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Updated: May 21, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
N-[4-(4-Chloro-benzene-sulfonamido)-phenyl-sulfon-yl]acetamide
Abstract:
In the title compound, C(14)H(13)ClN(2)O(5)S(2), the dihedral angles between the central benzene ring and the pendant chloro-benzene ring and the N-acetyl group are 82.35 (5) and 79.71 (6)°, respectively, and the overall conformation of the mol-ecule approximates to a U shape. Both the C-S-N-C conformations are gauche, but with opposite senses [torsion angles = -59.29 (15) and 63.68 (16)°]. An intra-molecular C-H⋯O inter-action generates an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(20) loops. A second N-H⋯O hydrogen bond links the dimers into (101) layers.
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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.
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Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
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