2-Amino-5-chloro-pyridinium (Z)-3-carb-oxy-prop-2-enoate 0.25-hydrate
Madhukar Hemamalini1, Hoong-Kun Fun
1X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Abstract:
In the title hydrated salt, C(5)H(6)ClN(2) (+)·C(4)H(3)O(4) (-)·0.25H(2)O, the water O atom lies on a twofold axis with 0.25 occupancy. The 2-amino-5-chloro-pyridinium cation is almost planar, with a maximum deviation of 0.015 (3) Å. In the hydrogen malate anion, an intra-molecular O-H⋯O hydrogen bond generates an S(7) ring and results in a folded conformation. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl-ate O atoms of the anion via a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. The ion pairs are further connected via O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, forming layers parallel to the ab plane which stack down the c axis.
More Related Videos
Related Concept Videos
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...
Diazonium Group Substitution: –OH and –H
Aldehydes and Ketones with Water: Hydrate Formation
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Acid-Catalyzed Hydration of Alkenes


