Reaction of nitric oxide with alkaline hydroxylamine

Cooper, John Neale; Chilton, J.E.; Powell, Richard E.

doi:10.1021/ic50092a020

Cited by 19 publications

(4 citation statements)

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“…Concerning NH 2 OH, it is important to note that in our experimental conditions we were working at pH 7, where the predominant species is by far 1 HNO. Cooper et al showed that hydroxylamine reacts with azanone to yield equimolar quantities of N 2 and H 2 O, but this occurs at a basic pH, where the reacting species is most probably 3 NO¯. Thus, under the present conditions, hydroxylamine is not expected to act as an azanone consuming agent.…”

Section: Resultsmentioning

confidence: 71%

Time-Resolved Electrochemical Quantification of Azanone (HNO) at Low Nanomolar Level

et al. 2013

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Azanone (HNO, nitroxyl) is a highly reactive and short-lived compound with intriguing and highly relevant properties. It has been proposed to be a reaction intermediate in several chemical reactions and an in vivo, endogenously produced key metabolite and/or signaling molecule. In addition, its donors have important pharmacological properties. Therefore, given its relevance and elusive nature (it reacts with itself very quickly), the development of reliable analytical methods for quantitative HNO detection is in high demand for the advancement of future research in this area. During the past few years, several methods were developed that rely on chemical reactions followed by mass spectrometry, high-performance liquid chromatography, UV-vis, or fluorescence-trapping-based methodologies. In this work, our recently developed HNO-sensing electrode, based on the covalent attachment of cobalt(II) 5,10,15,20-tetrakis[3-(p-acetylthiopropoxy)phenyl] porphyrin [Co(P)] to a gold electrode, has been thoroughly characterized in terms of sensibility, accuracy, time-resolved detection, and compatibility with complex biologically compatible media. Our results show that the Co(P) electrode: (i) allows time-resolved detection and kinetic analysis of the electrode response (the underlying HNO-producing reactions can be characterized) (ii) is able to selectively detect and reliably quantify HNO in the 1-1000 nM range, and (iii) has good biological media compatibility (including cell culture), displaying a lack of spurious signals due to the presence of O2, NO, and other reactive nitrogen and oxygen species. In summary, the Co(P) electrode is to our knowledge the best prospect for use in studies investigating HNO-related chemical and biological reactions.

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Section: Resultsmentioning

confidence: 71%

Time-Resolved Electrochemical Quantification of Azanone (HNO) at Low Nanomolar Level

et al. 2013

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“…Indeed, a radical mechanism has been described for the reaction of free NO with HA, forming N 2 O, Eqs. (6) and (7) [8,40]. Reactions (4)- (6), and (7) support the production of N 2 O and N 2 as unique oxidized nitrogen containing species.…”

Section: Formation Of An Initialmentioning

confidence: 84%

Disproportionation of hydroxylamine by water-soluble iron(III) porphyrinate compounds

Bari

Amorebieta

Gutiérrez

et al. 2010

Journal of Inorganic Biochemistry

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“…The products of disproportionation are NH3, N2, and N20. Hieber On the basis of this evidence, Nast and Foppl20 proposed that the primary disproportionative process is the reaction 2NH2OH = NH3 + HNO + HzO (9) and that the distribution of final gaseous products is dependent upon pH, i.e., that reduction of HNO to N2 predominates in alkaline solution but dimerization to N20 predominates at acidic pH. Kinetic measurements have been carried out in strong base by Holzapfel,21 who claimed an approximately first-order reaction in NH2OH but observed a shift in stoichiometry occurring with increasing depletion of NH2OH.…”

Section: Resultsmentioning

confidence: 99%

Properties of nitroxyl as intermediate in the nitric oxide-hydroxylamine reaction and in trioxodinitrate decomposition

Bonner¹,

Dzelzkalns²,

Bonucci³

1978

Inorg. Chem.

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The rate of decomposition of trioxodinitrate monobasic anion (HN2O3-) in aqueous solution is unaffected by the presence of hydroxylamine, but the primary product nitroxyl ("0) experiences a competition between dimerization to N 2 0 and reduction to N2. The proportion of N2 increases with pH and with NHzOH concentration; at pH 8, with N H 2 0 H in 10-fold excess over HN203-, the reaction product is more than 97% N2. The reaction between NO and N H 2 0 H produces equimolar amounts of N2 and N 2 0 at pH >13, but the ratio N Z / N 2 0 decreases with pH; at pH 8 the product is almost entirely N20.The rate of reaction declines sharply with decreasing pH. Observations of reaction product ratios are complicated by simultaneous contributions of ",OH disproportionation, which produces N2 and NzO in pH-dependent proportions. Tracer experiments employing 15N180 reactant confirm a previously proposed mechanistic interpretation of the NO-NHzOH reaction in detail: an N-bound H atom is abstracted by NO to form H N O and the radical NHOH. The radical combines with a second N O molecule to form nitrosohydroxylamine, which in turn produces two kinds of N20: I, predominantly 14N15N180, and 11, predominantly I5Nl4Ni6O. The asymmetry of the intermediate is reflected in a higher proportion of I than I1 in the product at high pH, but these proportions become equalized at pH 8, probably because of tautomerism in the intermediate. Nitroxyl is entirely reduced by NHzOH to N2 at high pH but undergoes dimerization to produce a third kind of N 2 0 , predominantly 15N1SNis0, to an extent that increases with decreasing pH. The tracer experiments also provide support for the hypothesis that nitroxyl is a primary product of hydroxylamine disproportionation. Since the nitroxyl produced in "203-decomposition is preferentially reduced to Nz at pH 8 in the presence of ",OH, while the nitroxyl produced in the NO-NH20H reaction is almost entirely consumed by self-reaction at the same pH, different intermediate species are produced in these two reactions. Possible explanations for this difference are discussed.

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Reaction of nitric oxide with alkaline hydroxylamine

Cited by 19 publications

References 0 publications

Time-Resolved Electrochemical Quantification of Azanone (HNO) at Low Nanomolar Level

Time-Resolved Electrochemical Quantification of Azanone (HNO) at Low Nanomolar Level

Disproportionation of hydroxylamine by water-soluble iron(III) porphyrinate compounds

Properties of nitroxyl as intermediate in the nitric oxide-hydroxylamine reaction and in trioxodinitrate decomposition

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