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Updated: Jun 1, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
(±)-3-Carb-oxy-2-(imidazol-3-ium-1-yl)-propanoate
Sarah A Reeb1, Marlesa C Shields, Kraig A Wheeler
1Eastern Illinois University, Department of Chemistry, 600 Lincoln Avenue, Charleston, IL 61920-3099, USA.
Abstract:
The title compound, C(7)H(8)N(2)O(4), crystallizes as a zwitterion, with mol-ecules organized into mol-ecular sheets via carbox-yl-carboxyl-ate and N(+)-H⋯carboxyl-ate contacts. These sheets are constructed from translationally related mol-ecules that further link to neighboring motifs via π-stacking [centroid-centroid distance 3.504 (3) Å] and weak C-H⋯O contacts.
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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.
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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 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.
IUPAC Nomenclature of Carboxylic Acids
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