Nitroxyl is the common chemical name for HNO, azanone being its IUPAC name. It is well known in the gas phase. In aqueous solution it acts as an acid with the conjugate base NO−, (pKa = 11.4). 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  such donor is prepared by organic oxidation of cyclohexanone oxime with lead tetraacetate to 1-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. 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. 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.
- ^ 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
- ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 0080379419.
- ^ Egon Wiberg, Arnold Frederick Holleman (2001) Inorganic Chemistry, Elsevier ISBN 0-12-352651-5
- ^ 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
- ^ 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
- ^ Cohen, A. D.; Zeng, B.-B.; King, S. B.; Toscano, J. P. J. Am. Chem. Soc. 2003, 125, 1444-1445.doi:10.1021/ja028978e
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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 ...
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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 ...
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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 ...
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The online retailer specializes in an all-natural supplement that is designed to enhance the body's ability to produce nitric oxide. Called Nitroxyl, it is an original formula that is made up of a variety of phytonutrients and other natural ingredients ...
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