39091-90-2Relevant academic research and scientific papers
New 4-aryl-1,3,2-oxathiazolylium-5-olates: Chemical synthesis and photochemical stability of a novel series of S-nitrosothiols
Eilertsen, Monica,Allin, Steve M.,Pearson, Russell J.
, p. 1106 - 1110 (2018/02/28)
S-nitrosothiols (RSNOs) remain one of the most popular classes of NO-donating compounds due to their ability to release nitric oxide (NO) under non-enzymatic means whilst producing an inert disulphide by-product. However, alligning these compounds to the different biological fields of NO research has proved to be problematic due to the inherent instability of such compounds under a variety of conditions including heat, light and the presence of copper ions. 1,3,2-Oxathiazolylium-5-olates (OZOs) represent an interesting subclass of S-nitrosothiols that lock the –SNO moiety into a five membered heterocyclic ring in an attempt to improve the compound's overall stability. The synthesis of a novel series of halogen-containing OZOs was comprehensively studied resulting in a seven-step route and overall yields ranging between 21 and 37%. The photochemical stability of these compounds was assessed to determine if S-nitrosothiols locked within these mesoionic ring systems can offer greater stability and thereby release NO in a more controllable fashion than their non-cyclic counterparts.
Viscosity-dependent Fluorescence and Low-temperature Photochemistry of Mesionic 4-Phenyl-1,3,2-oxathiazolylium-5-olate
Harrit, Niels,Holm, Arne,Dunkin, Ian R.,Poliakoff, Martin,Turner, James J.
, p. 1227 - 1238 (2007/10/02)
Irradiation of 4-phenyl-1,3,2-oxathiazolylium-5-olate (1) at cryogenic temperatures leads to formation of benzonitrile sulphide (4) and phenyl(nitrosothio)ketene (6) as primary products.They have been characterized by u.v. and i.r. spectroscopy.The relative yields of (4) and (6) depend strongly on the local viscosity of the medium.For example, poly(vinyl chloride) favours the formation of (4), whereas solid nitrogen favours (6).The observation of a strong fluorescence is also conditioned by a rigid environment.A vibrational fine structure extending half way through the main absorption band of (1) indicates the existence of a dissociative pathway in the excited singlet-state potential energy surface.This pathway is identified with the formation of (6).Isotopic labelling has been used to characterize (6) and the i.r. absorptions of its cis-trans-isomers have been located.The cis-isomer of (6) can regenerate (1) upon irradiation; similar treatment of the trans-isomer leads to the resonance-stabilized radical phenyl(oxomethylene)thiyl (7).
