Related Experiment Video
Updated: Jun 1, 2026

Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction
Published on: January 19, 2016
(E)-3-(3-Chloro-phen-yl)-N-(4-hy-droxy-3-meth-oxy-benz-yl)acryl-amide
Abstract:
In the title compound, C(17)H(16)ClNO(3), the 4-hy-droxy-3-meth-oxy-benzyl group is planar [maximum atomic deviation = 0.0138 (16) Å] and is nearly perpendicular to the chloro-benzene ring, making a dihedral angle of 84.67 (4)°. The chloro-benzene and amide groups are located on the opposite sides of the C=C bond, showing an E configuration. The relatively long C=O bond distance of 1.2364 (19) Å and the short C-N bond distance of 1.341 (2) Å suggest electron delocalization in the amide fragment. Inter-molecular O-H⋯O, N-H⋯O and weak C-H⋯O hydrogen bonding is present in the crystal structure.
Related Concept Videos
Nomenclature 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.
Structures 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...
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Amides to Carboxylic Acids: Hydrolysis
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
IUPAC Nomenclature of Aldehydes

