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Updated: May 31, 2026

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Published on: November 23, 2016
3-Diazo-N-[(2S)-1-hy-droxy-propan-2-yl]-2-oxopropanamide
Abstract:
In the title compound, C(6)H(9)N(3)O(3), the 3-diazo-2-oxopropan-amide section of the mol-ecule is nearly planar, with a maximum deviation of 0.025 (1) Å from the mean plane of its constituent atoms. The diazo C=N=N angle is 178.0 (3)°. In the crystal, pairs of inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into infinite double chains along the [100] direction. The double chains are additionally stabilized by weak C-H⋯O contacts with C⋯O distances of 3.039 (3) Å. Neighboring double chains in turn inter-act with each other through π-π stacking inter-actions [centroid-centroid distance of the 3-diazo-2-oxopropanamide units = 3.66 (6) Å] to form infinite stacks along the b axis. Mol-ecules from neighboring stacks inter-digitate with each other in the c-axis direction, thus leading to an inter-woven three-dimensional network held together by O-H⋯O, N-H⋯O and C-H⋯O inter-actions and π-π stacking.
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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.
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...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

