isonicotinic acid
{{chembox
|Watchedfields = changed
|verifiedrevid = 443884866
|Reference =[http://chemicalland21.com/lifescience/phar/ISONICOTINIC%20ACID.htm Isonicotinic acid] at chemicalland21.com
|Name = Isonicotinic acid
|ImageFileL1 = Isonicotinic acid.png
|ImageNameL1 = Skeletal formula
|ImageFileR1 = Isonicotinic-acid-3D-balls.png
|ImageNameR1 = Ball-and-stick model
|PIN = Pyridine-4-carboxylic acid
|OtherNames = Isonicotinic acid
4-Pyridinecarboxylic acid
p-Pyridinecarboxylic acid
4-Picolinic acid
|Section1={{Chembox Identifiers
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 6032
|SMILES = c1cnccc1C(=O)O
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 5709
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = Y8SYN761TQ
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C07446
|InChI = 1/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)
|InChIKey = TWBYWOBDOCUKOW-UHFFFAOYAV
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 1203
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = TWBYWOBDOCUKOW-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 55-22-1
|PubChem = 5922
}}
|Section2={{Chembox Properties
|C=6|H=5|N=1|O=2
|Appearance = White to off-white crystalline solid
|Density = Solid
|MeltingPtC = 310
|MeltingPt_notes = (sublimes)
}}
|Section7={{Chembox Hazards
|ExternalSDS =http://datasheets.scbt.com/sc-250188.pdf
|NFPA-F = 1
|NFPA-H = 3
|NFPA-R = 0
}}
|Section8={{Chembox Related
| OtherCompounds = nicotinic acid, pyridine isoniazid
}}
}}
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:
:{{chem2|NC5H4CH3 + 1.5 O2 + NH3 -> NC5H4C\tN + 3 H2O}}
:{{chem2|NC5H4C\tN + 2 H2O -> NC5H4CO2H + NH3}}
It is also produced by oxidation of 4-picoline with nitric acid.{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}
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{{cite journal |doi=10.1016/j.ccr.2005.07.008 |title=Self-assembly directed by dinuclear zinc(II) macrocyclic species |date=2006 |last1=Huang |first1=Wei |last2=Zhu |first2=Hai-Bin |last3=Gou |first3=Shao-Hua |journal=Coordination Chemistry Reviews |volume=250 |issue=3–4 |pages=414–423 }} and MOFs{{cite journal |doi=10.1021/jacs.8b07563 |title=Boosting Ethane/Ethylene Separation within Isoreticular Ultramicroporous Metal–Organic Frameworks |date=2018 |last1=Lin |first1=Rui-Biao |last2=Wu |first2=Hui |last3=Li |first3=Libo |last4=Tang |first4=Xiao-Liang |last5=Li |first5=Zhiqiang |last6=Gao |first6=Junkuo |last7=Cui |first7=Hui |last8=Zhou |first8=Wei |last9=Chen |first9=Banglin |journal=Journal of the American Chemical Society |volume=140 |issue=40 |pages=12940–12946 |pmid=30216725 }} by binding metal ions through both the N and carboxylate.
See also
References
{{reflist}}