Related Experiment Video
Updated: May 24, 2026

Synthesis of Strong Adhesive Hydrogel, Gelatin O-Nitrosobenzaldehyde
Published on: November 11, 2022
(E)-N-Butyl-3-(3,4-dihy-droxy-phen-yl)acryl-amide hemihydrate
1College of Chemistry and Chemical Engineering, Xinxiang University, Xinxiang, Henan 453003, People's Republic of China.
Abstract:
In the title compound, C(13)H(17)NO(3)·0.5H(2)O, a new caffeic acid amide derivative, the solvent water mol-ecule lies on a twofold axis and the terminal ethyl group appears disordered with occupancy factors of 0.525 (6) and 0.475 (6). The benzene ring makes an angle of 17.3 (2)° with the C=C-C-O linker. The presence of an ethyl-enic spacer in the caffeic acid amide mol-ecule allows the formation of a conjugated system, strongly stabilized through π-electron delocalization. The C=C double bond in the linker is trans, similar to those previously reported in caffeic esters. The crystal is stabilized by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds. The mol-ecules of the caffeic acid amide form a supermolecular planar structure through O-H⋯O hydrogen bonds between a hy-droxy group of one caffeic acid mol-ecule and a carbonyl O atom of another. These planes inter-act via C-H⋯O, O-H⋯O and N-H⋯O hydrogen bonds to form a three-dimensional network.
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 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.
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...
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
Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.

