Chelidamic acid

Structural formula
	Tautomeric boundary structures
General
Surname	Chelidamic acid
other names	4-hydroxypyridine-2,6-dicarboxylic acid; 1,4-dihydro-4-oxo-2,6-pyridinedicarboxylic acid;
Molecular formula	C 7 H 5 NO 5
Brief description	white to yellowish solid
External identifiers / databases
EC number	205-335-8
ECHA InfoCard	100.004.851
PubChem	8743
ChemSpider	8413
Wikidata	Q2667856
properties
Molar mass	183.12 g mol −1 ; 201.14 g mol −1 (monohydrate);
Physical state	firmly
Melting point	267 ° C (decomposition, monohydrate)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chelidamic acid is a chemical compound from the group of heterocycles . It consists of a pyridine ring with carboxy groups in the 2- and 6-position and a hydroxyl group in the 4-position.

properties

Chelidamic acid is a white to slightly yellowish compound. It crystallizes out as a monohydrate from aqueous solution. Chelidamic acid monohydrate decomposes at 267 ° C. Chelidamic acid has two tautomeric forms, an aromatic enol form and a keto form . The monohydrate forms a zwitterionic structure in the crystal . In this one carboxylic acid group is deprotonated and the nitrogen is protonated.

Manufacturing

Chelidamic acid can be produced by reacting chelidonic acid with ammonia .

use

Chelidamic acid can be used as a starting material for the synthesis of heterocyclic compounds. The hydroxy group can easily be substituted . The carboxylic acid groups can be used to build larger structures.
Chelidamic acid forms stable complexes with many metal ions . It acts as a tridentate chelating ligand .

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet Chelidamic acid hydrate from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).
↑ AK Hall, JM Harrowfield, BW Skelton, AH White: Chelidamic acid monohydrate: the proton complex of a multidentate ligand , in Acta. Cryst. 2000 , C56 , pp. 448-450; doi: 10.1107 / S0108270199015620 .
↑ L. Haitinger, A. Lieben: Investigations on chelidonic acid , in: Monatsh. Chem. 1885 , 6 , pp. 279-328; doi: 10.1007 / BF01554631 .
↑ MK Tse, S. Bhor, M. Klawonn, G. Anilkumar, H. Jiao, C. Döbler, A. Spannenberg, W. Mägerlein, H. Hugl, M. Beller: Ruthenium-Catalyzed Asymmetric Epoxidation of Olefins Using H2O2, Part I: Synthesis of New Chiral N , N , N -Tridentate Pybox and Pyboxazine Ligands and Their Ruthenium Complexes , in: Chemistry 2006 , 12 , pp. 1855-1874; doi: 10.1002 / chem.200501261 .

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet Chelidamic acid hydrate from Sigma-Aldrich , accessed on March 16, 2011 ( PDF ).

[2] AK Hall, JM Harrowfield, BW Skelton, AH White: Chelidamic acid monohydrate: the proton complex of a multidentate ligand , in Acta. Cryst. 2000 , C56 , pp. 448-450; doi: 10.1107 / S0108270199015620 .

[3] L. Haitinger, A. Lieben: Investigations on chelidonic acid , in: Monatsh. Chem. 1885 , 6 , pp. 279-328; doi: 10.1007 / BF01554631 .

[4] MK Tse, S. Bhor, M. Klawonn, G. Anilkumar, H. Jiao, C. Döbler, A. Spannenberg, W. Mägerlein, H. Hugl, M. Beller: Ruthenium-Catalyzed Asymmetric Epoxidation of Olefins Using H2O2, Part I: Synthesis of New Chiral N , N , N -Tridentate Pybox and Pyboxazine Ligands and Their Ruthenium Complexes , in: Chemistry 2006 , 12 , pp. 1855-1874; doi: 10.1002 / chem.200501261 .