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Updated: Jun 5, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
Published on: February 7, 2017
A new polymorph of N-(prop-2-yn-yl)tricyclo-[3.3.1.1]decane-1-carbox-amide
Abstract:
The alkynyl bond of the title compound, C(14)H(19)NO, has a length of 1.170 (5) Å. The amide function shows a trans conformation with respect to the carbonyl group characterized by the torsion angle O-C-N-H of -176 (2)°. There is an inter-molecular N-H⋯O hydrogen bond between the amide function and the carbonyl group. In addition, weak inter-molecular hydrogen bonds stabilize the crystal structure. A comparison with a polymorphic structure shows conformational differences with regard to the orientation of the carbonyl groups with respect to the adamantyl group [O-C-C-C = 96.2 (3)° in the title compound and 123.7 (2)° in the polymorph] and the orientations of the propargyl groups in relation to the carbonyl groups [O-C-C-C = -87.7 (3) and -58.7 (2)°, respectively].
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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.
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For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic 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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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.

