Organic & Biomolecular Chemistry
Controlling S-nitrosothiols decomposition, with the consequent release of nitric oxide, is a topic of great research effort. Nitrosomercaptopyridine (SNO+) incorporation into cucurbituril cavity results in a large increase of its nitrosation equilibrium constant. This effect being a consequence of the stabilization of organic cations by formation of host:guest complexes with CB7 resulting in a drastic reduction of the SNO+ denitrosation rate constant. Moreover SNO+ encapsulation also prevents its decomposition yielding disulfide and nitric oxide. Expulsion of SNO+ from the cucurbirutil cavity by using a competitive guest results nitric oxide release as was confirmed by using a NO selective electrode.