Reaction of hydroxylamine with benzenesulfonyl chloride. X-ray crystal structure of piloty's acid and other benzenesulfonylhydroxylamines

Scholz, John N.; Engel, Paul S.; Glidewell, Christopher; Whitmire, Kenton H.

doi:10.1016/s0040-4020(01)85786-0

Cited by 22 publications

(15 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The analysis agreed with the previously reported ones [35][36][37]. The amount of solvent present in the molecular formula was determined by 1 H NMR spectra and microanalysis.…”

Section: Instrumental Proceduressupporting

confidence: 89%

The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: azanone donors at biological pH

Sirsalmath

Suárez

Bikiel

et al. 2013

Journal of Inorganic Biochemistry

View full text Add to dashboard Cite

“…The analysis agreed with the previously reported ones [35][36][37]. The amount of solvent present in the molecular formula was determined by 1 H NMR spectra and microanalysis.…”

Section: Instrumental Proceduressupporting

confidence: 89%

The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: azanone donors at biological pH

Sirsalmath

Suárez

Bikiel

et al. 2013

Journal of Inorganic Biochemistry

View full text Add to dashboard Cite

“…First reported in 1896, Piloty's acid (N-hydroxybenzenesulfonamide, C 6 H 5 SO 2 NHOH, CAS 599-71-3) is available commercially and can also be synthesized by condensation of hydroxylamine with benzenesulfonyl chloride to give a solid product in 45%-55% yield after column chromatographic purification ( Fig. 7) (12,71). A similar procedure yields 15 N-labeled Piloty's acid (12).…”

Section: Structure/synthesismentioning

confidence: 99%

The Chemistry of Nitroxyl-Releasing Compounds

DuMond

King

2011

Antioxidants & Redox Signaling

View full text Add to dashboard Cite

Nitroxyl (HNO) demonstrates a diverse and unique biological profile compared to nitric oxide, a redox-related compound. Although numerous studies support the use of HNO as a therapeutic agent, the inherent chemical reactivity of HNO requires the use of donor molecules. Two general chemical strategies currently exist for HNO generation from nitrogen-containing molecules: (i) the disproportionation of hydroxylamine derivatives containing good leaving groups attached to the nitrogen atom and (ii) the decomposition of nitroso compounds (X-N=O, where X represents a good leaving group). This review summarizes the synthesis and structure, the HNO-releasing mechanisms, kinetics and by-product formation, and alternative reactions of six major groups of HNO donors: Angeli's salt, Piloty's acid and its derivatives, cyanamide, diazenium diolate-derived compounds, acyl nitroso compounds, and acyloxy nitroso compounds. A large body of work exists defining these six groups of HNO donors and the overall chemistry of each donor requires consideration in light of its ability to produce HNO. The increasing interest in HNO biology and the potential of HNO-based therapeutics presents exciting opportunities to further develop HNO donors as both research tools and potential treatments.

show abstract

“…The bond lengths within the SO 2 NOC fragments are typical of those observed in sulfonylhydroxylamines, such as PhSO 2 -NHOH and PhSO 2 NHOSO 2 Ph (Scholz et al, 1989). In the aryl rings, the Cn1ÐCn2 and Cn1ÐCn6 bonds (n = 1 or 2), adjacent to the sulfonyl substituents, have distances in the range 1.410 (2)±1.414 (2) A Ê , signi®cantly longer than the other bonds in these rings, for which the distances lie in the range 1.382 (3)±1.399 (2) A Ê (mean 1.389 A Ê ; Table 1).…”

Section: Commentmentioning

confidence: 80%

N,N′-Propylenedioxybis(2,4,6-trimethylbenzenesulfonamide): molecules of unexpected conformation form a molecular ladder built from two independent N—H...O=S hydrogen bonds

et al. 2004

Self Cite

View full text Add to dashboard Cite

show abstract

Reaction of hydroxylamine with benzenesulfonyl chloride. X-ray crystal structure of piloty's acid and other benzenesulfonylhydroxylamines

Cited by 22 publications

References 22 publications

The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: azanone donors at biological pH

The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: azanone donors at biological pH

The Chemistry of Nitroxyl-Releasing Compounds

N,N′-Propylenedioxybis(2,4,6-trimethylbenzenesulfonamide): molecules of unexpected conformation form a molecular ladder built from two independent N—H...O=S hydrogen bonds

Contact Info

Product

Resources

About