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Nitroxyl
Ball and stick model of nitroxyl
Names
IUPAC name
Azanone
Systematic IUPAC name
Oxidanimine[citation needed]
Other names
Hydrogen oxonitrate(I)

Nitronous oxide

Nitrosyl hydride
Identifiers
14332-28-6
ChEMBL ChEMBL1200689 YesY
ChemSpider 920 YesY
Jmol-3D images Image
MeSH Nitroxyl
PubChem 945
Properties
HNO
Molar mass 31.01 g·mol−1
log P 0.74
Structure
Digonal
Molecular shape Dihedral
Thermochemistry
33.88 J K−1 mol−1
220.91 J K−1 mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Nitroxyl is the common chemical name for HNO, azanone being its IUPAC name.[1] It is well known in the gas phase.[2] In aqueous solution it acts as an acid with the conjugate base NO, (pKa = 11.4).[3] NO is the reduced form of nitric oxide (NO) and is isoelectronic with dioxygen. Nitroxyl can be formed as a reaction intermediate.
Nitroxyl is very reactive towards nucleophiles (especially thiols) and quickly dimerizes to hyponitrous acid, H2N2O2, which is then dehydrated to nitrous oxide N2O. Therefore, HNO is generally prepared in situ for example with the compounds such as Angeli’s salt (Na2N2O3) and Piloty’s acid (PhSO2NHOH) when it is needed.

Nitroxyl shows potential in the treatment of heart failure and ongoing research is focused on finding new nitroxyl donors. In one study [4] such donor is prepared by organic oxidation of cyclohexanone oxime with lead tetraacetate to 1-nitrosocyclohexyl acetate:

Nitrosocyclohexyl acetate

This compound can be hydrolyzed under basic conditions in a phosphate buffer to nitroxyl HNO, acetic acid and cyclohexanone.

Other studies that have been conducted on HNO precursors include those from Nagasawa et al.[5] in which Piloty's acid is derivatized and produces HNO upon thermal decomposition. Other notable studies on the production of HNO come from Toscano et al.[6] in which cycloadducts of acyl nitroso species (which are known to decompose via hydrolysis to HNO and acyl acid) are synthesized. Upon photolysis these compounds release the acyl nitroso species which then further decomposes.

References[edit]

  1. ^ Nitroxyl (azanone) trapping by metalloporphyrinsDoctorovich, F., Bikiel, D., Pellegrino, J., Suárez, S.A., Larsen, A., Martí, M.A.2011Coordination Chemistry Reviews255(23-24), pp. 2764-2784
  2. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 0080379419. 
  3. ^ Egon Wiberg, Arnold Frederick Holleman (2001) Inorganic Chemistry, Elsevier ISBN 0-12-352651-5
  4. ^ Hydrolysis of Acyloxy Nitroso Compounds Yields Nitroxyl (HNO) Xin Sha, T. Scott Isbell, Rakesh P. Patel, Cynthia S. Day, and S. Bruce King J. Am. Chem. Soc.; 2006; 128(30) pp 9687 - 9692; (Article) doi: 10.1021/ja062365a
  5. ^ Prodrugs of Nitroxyl as Potential Aldehyde Dehydrogenase Inhibitors vis-a-vis Vascular Smooth Muscle Relaxants Nagasawa, H. T.; Kawle, S. P.; Elberling, J. A.; DeMaster, E. G.; Fukuto, J. M. J. Med. Chem., 38, 1865-1871. doi:10.1021/jm00011a005
  6. ^ Cohen, A. D.; Zeng, B.-B.; King, S. B.; Toscano, J. P. J. Am. Chem. Soc. 2003, 125, 1444-1445.doi:10.1021/ja028978e

Original courtesy of Wikipedia: http://en.wikipedia.org/wiki/Nitroxyl — Please support Wikipedia.
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51 news items

Phys.Org

Phys.Org
Thu, 19 Mar 2015 06:20:07 -0700

Wang and Groves began by oxidizing APO using mCPBA, and then determined that the reduction of APO-I using a nitroxyl radical would provide APO-II. They tested their nitroxyl radical candidates using a model system, ensuring that they would get complete ...

DocCheck News

DocCheck News
Wed, 16 Jul 2014 06:18:45 -0700

Bessere Durchblutung, ein niedriger Blutdruck und ein kräftiges Herz – diese Effekte wiesen Wissenschaftler nun bei der Erforschung des bisher wenig beachteten Wirkstoffes Nitroxyl nach. Gleichzeitig zeigten sie dessen Grenzen auf: Nitroxyl kann auch ...
 
PR Newswire (press release)
Wed, 18 Sep 2013 11:43:26 -0700

18, 2013 /PRNewswire-iReach/ -- Nitro Solution, a website that offers high quality and all-natural nitric oxide supplements, has just launched its brand new and user-friendly site. In addition to featuring the safe and innovative supplement called ...
 
Window on Wake Forest
Sun, 05 Jul 2009 23:00:00 -0700

Wake Forest University scientists have developed a new research tool in the pursuit of heart medications based on the compound nitroxyl by identifying unique chemical markers for its presence in biological systems. Nitroxyl, a cousin to the blood ...

Jewish Business News

Jewish Business News
Sun, 15 Mar 2015 09:52:30 -0700

Technion scientists have developed the alpha hydrogen nitroxyl radical – a new stable class of chemical that encourages other chemicals to react together without being affected itself. This has major implications for chemical and medical industries ...
 
PR Newswire (press release)
Thu, 20 Nov 2014 06:15:00 -0800

Nitroxyl, the chemical name for HNO, has been studied for its potential as a treatment for heart failure; it acts to dilate blood vessels and works directly on the heart through a unique mechanism to enhance both systolic and diastolic cardiac function.
 
MarketWatch
Mon, 28 Jul 2014 05:22:30 -0700

About CXL-1427CXL-1427 is a novel, improved second-generation prodrug that breaks down chemically to produce nitroxyl (HNO) and an inactive byproduct following intravenous administration. In extensive pre-clinical testing and in a Phase IIa human ...

הידען

הידען
Sun, 08 Feb 2015 08:07:30 -0800

המולקולה החדשה שפיתח פרופסור-משנה שפילמן – stable α-hydrogen nitroxyl radical – עשויה לחולל שינוי דרמטי בתחום זה. זהו רדיקל יציב בעל מבנה מרחבי 'שמיש' יותר. בסיום המאמר מציין פרופסור-משנה שפילמן כי מולקולה זו אטרקטיבית במיוחד בהקשר של יישומים עתידיים בקטליזה ובהקשר ...
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