Pyridine-3-sulfonic acid

Structural formula
General
Surname	Pyridine-3-sulfonic acid
other names	3-pyridinesulfonic acid; β-pyridinesulfonic acid;
Molecular formula	C 5 H 5 NO 3 S
Brief description	white solid
External identifiers / databases
EC number	211-265-9
ECHA InfoCard	100.010.242
PubChem	69468
ChemSpider	62675
Wikidata	Q1682463
properties
Molar mass	159.17 g mol −1
Physical state	firmly
density	1.72 g cm −3
Melting point	357 ° C
solubility	soluble in water
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 314
	P: 280-305 + 351 + 338-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pyridine-3-sulfonic acid is an organic compound which consists of a pyridine ring with a sulfonic acid group in the 3-position .

presentation

The compound can be prepared by sulfonating pyridine. However, electrophilic aromatic substitutions take place only with difficulty on pyridine and the reaction of pyridine with sulfuric acid does not give any appreciable amounts of pyridine-3-sulfonic acid even under severe conditions. However, it is accessible in acceptable yield by boiling in an excess of fuming sulfuric acid at 320 ° C. The reason for the poor yields is the preferred addition of the electrophile sulfur trioxide to the pyridine nitrogen, as a result of which the heteroaromatic is additionally deactivated for electrophilic attack. However, the sulfonation with oleum proceeds smoothly in the presence of catalytic amounts of mercury (II) sulfate . The underlying mechanism has not yet been clarified.

properties

Pyridine-3-sulfonic acid is a white solid that melts at 357 ° C. It crystallizes in prismatic rods in the orthorhombic crystal system with the lattice parameters a = 11.41 Å , b = 15.08 Å and c = 7.20 Å with 8 formula units per unit cell .

Individual evidence

↑ ^a ^b ^c ^d Data sheet pyridine-3-sulfonic acid (PDF) from Merck , accessed on June 4, 2010.
↑ ^a ^b Beta-Pyridinesulfonic Acid , in: Anal. Chem. 1948 , 20 , 879; doi : 10.1021 / ac60021a602 .
↑ ^a ^b Data sheet 3-Pyridinesulfonic acid from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).
↑ O. Fischer : Note on nicotinic acid from pyridine , in: Chem. Ber. , 1882 , 15 , pp. 62-64; doi : 10.1002 / cber.188201501180 .
↑ ^a ^b J. A. Joule, K. Mills: Heterocyclic Chemistry 3rd Edition, 2004 , Blackwell Science, Oxford, ISBN 0-632-05453-0 .
^ EF Möller, L. Birkofer: Constitutional specificity of nicotinic acid as a growth substance in Proteus vulgaris and Streptobacterium plantarum , in: Chem. Ber. , 1942 , 75 , pp. 1108-1118; doi : 10.1002 / cber.19420750912 .

[merck-1] Data sheet pyridine-3-sulfonic acid (PDF) from Merck , accessed on June 4, 2010.

[ac-2] Beta-Pyridinesulfonic Acid , in: Anal. Chem. 1948 , 20 , 879; doi : 10.1021 / ac60021a602 .

[Sigma-3] Data sheet 3-Pyridinesulfonic acid from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

[4] O. Fischer : Note on nicotinic acid from pyridine , in: Chem. Ber. , 1882 , 15 , pp. 62-64; doi : 10.1002 / cber.188201501180 .

[jou-5] J. A. Joule, K. Mills: Heterocyclic Chemistry 3rd Edition, 2004 , Blackwell Science, Oxford, ISBN 0-632-05453-0 .

[6] EF Möller, L. Birkofer: Constitutional specificity of nicotinic acid as a growth substance in Proteus vulgaris and Streptobacterium plantarum , in: Chem. Ber. , 1942 , 75 , pp. 1108-1118; doi : 10.1002 / cber.19420750912 .