Isonicotinic acid or pyridine-4-carboxylic acid is an organic compound with the formula C5H4N(CO2H). It is a derivative of pyridine with a carboxylic acid substituent at the 4-position. It is an isomer of picolinic acid and nicotinic acid, which have the carboxyl group at the 2- and 3-position respectively compared to the 4-position for isonicotinic acid.
Production
On a commercial scale, isonicotinic acid, like other pyridine carboxylic acid is produced by ammoxidation of 4-picoline (4-methylpyridine) followed by hydrolysis of the resulting nitrile:
- NC5H4CH3 + 1.5 O2 + NH3 → NC5H4C≡N + 3 H2O
- NC5H4C≡N + 2 H2O → NC5H4CO2H + NH3
It is also produced by oxidation of 4-picoline with nitric acid.[2]
Derivatives
Isonicotinic acids is a term loosely used for derivatives of isonicotinic acid. Hydrazide derivatives include isoniazid, iproniazid, and nialamide. Amide and ester derivatives include ethionamide and dexamethasone isonicotinate.
Its conjugate base forms coordination polymers[3] and MOFs[4] by binding metal ions through both the N and carboxylate.
See also
References
- ^ Isonicotinic acid at chemicalland21.com
- ^ Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3-527-30673-2.
- ^ Huang, Wei; Zhu, Hai-Bin; Gou, Shao-Hua (2006). "Self-assembly directed by dinuclear zinc(II) macrocyclic species". Coordination Chemistry Reviews. 250 (3–4): 414–423. doi:10.1016/j.ccr.2005.07.008.
- ^ Lin, Rui-Biao; Wu, Hui; Li, Libo; Tang, Xiao-Liang; Li, Zhiqiang; Gao, Junkuo; Cui, Hui; Zhou, Wei; Chen, Banglin (2018). "Boosting Ethane/Ethylene Separation within Isoreticular Ultramicroporous Metal–Organic Frameworks". Journal of the American Chemical Society. 140 (40): 12940–12946. doi:10.1021/jacs.8b07563. PMID 30216725.
External links
- Isonicotinic+Acids at the U.S. National Library of Medicine Medical Subject Headings (MeSH)