Methylsulfonylhydroxylamin

Abstract

Methylsulfonylhydroxylamin, CH3SO2NHOH, entsteht bei der Umsetzung von Methylsulfonylchlorid mit freiem Hydroxylamin. Diese Verbindung aus der Klasse der Alkylsulfhydroxamsäuren (pKS = 9,95) wurde IR‐, UV‐, NMR‐ und massenspektroskopisch charakterisiert. Ihre saure und alkalische Hydrolyse werden beschrieben.

Synthesis and HNO Donating Properties of the Piloty's Acid Analogue Trifluoromethanesulphonylhydroxamic Acid: Evidence for Quantitative Release of HNO at Neutral pH Conditions

“…The rate constant for decomposition of CF 3 SO 2 NHO − is larger than that observed for deprotonated MSHA ( k =8.25×10 −3 min −1[28] ) and deprotonated PA ( k =2.53×10 −2 min −1[15] ). However, the most significant advantage of CF 3 SO 2 NHOH is that, unlike MSHA (p K a 9.95) and PA (p K a 9.29), this new HNO analogue is almost entirely deprotonated at pH 7.0 (p K a =5.89±0.05). Therefore, unlike MSHA and PA, CF 3 SO 2 NHOH is an excellent HNO donor molecule for studies at neutral pH conditions.…”

“…The most widely used HNO donor is Angeli's salt (diazen‐1‐ium‐1,2,2‐triolate, Na 2 N 2 O 3 , AS) . Other well‐established HNO donors are the N ‐hydroxysulphonamides methanesulphohydroxamic acid (CH 3 SO 2 NHOH, MSHA) and benzenesulphohydroxamic acid, Piloty's acid (C 6 H 5 SO 2 NHOH, PA) . In contrast to AS which spontaneously decomposes to release HNO at neutral pH conditions, a major drawback of PA and MSHA is that alkaline conditions are required for the deprotonation and subsequent release of HNO from these molecules (Scheme , p K a (PA)=9.29; pK a (MSHA)=9.95) …”

Donors of HNO

“…8). (8) Piloty's acid is the most commonly used organic donor of HNO, but similar derivatives, such as hydroxylamine-Nsulfonic acid (HOSO 2 NHOH) [83] and N-hydroxymethanesulfonamide (methanesulfohydroxamic acid (MSHA), methylsulfonylhydroxylamine; CH 3 SO 2 NHOH) [84], have been used with increasing frequency.…”

Mesylhydroxylamine, IV [1] Silylierte N-Mesylhydroxylamine / Mesylhydroxylamines, IV [1] Silylated N-Mesylhydroxylamines

“…(2 a) a) Zur Suspension von 55,6 g (0,5 mol) feinkristallinem 1 [7] in 500 ml Ether werden 32,3 g (0,2 mol) HN[Si(CH3)3]2 getropft und so lange unter Rückfluß erhitzt, bis die NH3-Entwicklung beendet ist (ca. 7 h).…”