4-Nitropyridine-N-oxide

4-Nitropyridine-N-oxide
Names
	Preferred IUPAC name 4-Nitropyridin-1-ium-1-olate
Identifiers
CAS Number	1124-33-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	13662;
ECHA InfoCard	100.013.088
PubChem CID	14300;
UNII	ULB29Z652D ;
CompTox Dashboard (EPA)	DTXSID9041524 ;
	InChI InChI=1S/C5H4N2O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4H Key: RXKNNAKAVAHBNK-UHFFFAOYSA-N; InChI=1/C5H4N2O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4H Key: RXKNNAKAVAHBNK-UHFFFAOYAT;
	SMILES c1c[n+](ccc1[N+](=O)[O-])[O-];
Properties
Chemical formula	C5H4N2O3
Molar mass	140.098 g·mol−1
Structure
Space group	Pnma
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Nitropyridine-N-oxide is a chemical compound, crystallizing in space group Pnma.^[1]

It is highly toxic when consumed orally.^[2] It is also weakly carcinogenic, requiring a pre-existing oncovirus infection to have any effect.^[3]

E. coli bacteria struggle to sense quorum in the presence of para-nitropyridine oxide,^[4] and the compound physically prevents P. aeruginosa from adhering to surfaces.^[5]

para-Nitropyridine oxide also forms cocrystals. The cocrystal with mercuric chloride links together the molecular π systems, generating a large third harmonic response.^[6] The 1:1 cocrystal with nitrophenol also exhibits nonlinear optical effects, presumably due to strong hydrogen bonding.^[7]

References

1 2 Eichhorn, Edgar L. (1956) [16 January 1956]. "On the structure of 4-nitropyridine-N-oxide". Acta Crystallographica. 9 (10): 787–793. Bibcode:1956AcCry...9..787E. doi:10.1107/S0365110X56002151.
↑ Pyridine, 4-nitro-, 1-oxide at cameochemicals.noaa.gov
↑ Price, Paul J.; Auletta, Angela E.; King, Martin P.; Hugunin, Patricia M.; Huebner, Robert J. (1976). "The co-carcinogenic activity of 4-nitropyridine-1-oxide (4-NPO) and prevention of transformation by type-specific anti-viral antibodies". In Vitro. 12 (8): 595–597. doi:10.1007/BF02797444. PMID 186397.
↑ Rasmussen, Thomas B.; Givskov, Michael (2006). "Quorum sensing inhibitors: a bargain of effects". Microbiology. 152 (4): 895–904. doi:10.1099/mic.0.28601-0. PMID 16549654.
↑ Vanoyan, Nune; Walker, Sharon L.; Gillor, Osnat; Herzberg, Moshe (16 June 2010) [May 6, 2010]. "Reduced bacterial deposition and attachment by quorum-sensing inhibitor 4-nitro-pyridine-N-oxide". Langmuir. 26 (14). American Chemical Society: 12089–12094. doi:10.1021/la101319e. PMID 20553026.
↑ Newman, P.R., Warren, L.F., Cunningham, P. et al (1989). "Semiorganics: A New Class of NLO Materials", at the MRS Online Proceedings Library vol. 173, pp. 560–561 (1989). doi:10.1557/PROC-173-557
↑ Bueno, Willie A.; Blaz, Neide A.; Santos, Maria Julia M. (1984). "Hydrogen bonding between pyridine N-oxides and nitrophenols". Anais da ABC. 56 (1).

[Crystal-1] 1 2 Eichhorn, Edgar L. (1956) [16 January 1956]. "On the structure of 4-nitropyridine-N-oxide". Acta Crystallographica. 9 (10): 787–793. Bibcode:1956AcCry...9..787E. doi:10.1107/S0365110X56002151.

[2] Pyridine, 4-nitro-, 1-oxide at cameochemicals.noaa.gov

[3] Price, Paul J.; Auletta, Angela E.; King, Martin P.; Hugunin, Patricia M.; Huebner, Robert J. (1976). "The co-carcinogenic activity of 4-nitropyridine-1-oxide (4-NPO) and prevention of transformation by type-specific anti-viral antibodies". In Vitro. 12 (8): 595–597. doi:10.1007/BF02797444. PMID 186397.

[4] Rasmussen, Thomas B.; Givskov, Michael (2006). "Quorum sensing inhibitors: a bargain of effects". Microbiology. 152 (4): 895–904. doi:10.1099/mic.0.28601-0. PMID 16549654.

[5] Vanoyan, Nune; Walker, Sharon L.; Gillor, Osnat; Herzberg, Moshe (16 June 2010) [May 6, 2010]. "Reduced bacterial deposition and attachment by quorum-sensing inhibitor 4-nitro-pyridine-N-oxide". Langmuir. 26 (14). American Chemical Society: 12089–12094. doi:10.1021/la101319e. PMID 20553026.

[6] Newman, P.R., Warren, L.F., Cunningham, P. et al (1989). "Semiorganics: A New Class of NLO Materials", at the MRS Online Proceedings Library vol. 173, pp. 560–561 (1989). doi:10.1557/PROC-173-557

[7] Bueno, Willie A.; Blaz, Neide A.; Santos, Maria Julia M. (1984). "Hydrogen bonding between pyridine N-oxides and nitrophenols". Anais da ABC. 56 (1).

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