Related Experiment Video
Updated: Jun 1, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-2-Cyano-3-[4-(dimethyl-amino)phen-yl]-N-phenyl-prop-2-enamide
Abstract:
In the title compound, C(18)H(17)N(3)O, the dihedral angle between the phenyl and benzene rings is 11.22 (14)°. Apart from the methyl H atoms, the mol-ecule is close to planar, with a maximum deviation of 0.145 (3) Å. Intra-molecular C-H⋯O and C-H⋯N inter-actions occur. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds occur, resulting in an R(2) (2)(12) ring motif. Further C-H⋯N and C-H⋯O bonds generate R(1) (2)(7) and R(2) (2)(22) motifs and a C-H⋯π inter-action also occurs.
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.
Nomenclature of Primary Amines
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
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...
Aldehydes and Ketones with Amines: Enamine Formation Mechanism

