N-(4-Chloro-phenyl-sulfon-yl)-2,2,2-tri-methyl-acetamide
Abstract:
In the crystal structure of the title compound (N4CPSTMAA), C(11)H(14)ClNO(3)S, the conformations of the N-H and C=O bonds in the amide group are anti to each other, similar to those observed in N-phenyl-sulfonyl-2,2,2-trimethyl-acetamide (NPSTMAA) and 2,2,2-trimethyl-N-(4-methyl-phenyl-sulfon-yl)acetamide (N4MPSTMAA). The bond parameters in N4CPSTMAA are similar to those in NPSTMAA, N4MPSTMAA, N-aryl-2,2,2-trimethyl-acetamides and 4-chloro-benzene-sulfonamide. The -SNHCOC- unit including the amide group is essentially planar and makes a dihedral angle of 82.2 (1)° with the benzene ring, comparable to the values of 79.1 (1) and 71.2 (1)° in NPSTMAA and N4MPSTMAA, respectively. The mol-ecules in N4CPSTMAA are linked into a chain by inter-molecular N-H⋯O hydrogen bonds.
Related Concept Videos
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
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.
01:28Structures of Carboxylic Acid Derivatives
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...
01:15Carboxylic Acid Derivatives: Overview
01:16Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
01:19Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
02:30Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...