Proton Transfer Reactions of Triazol-3-ylidenes: Kinetic Acidities and Carbon Acid pKa Values for Twenty Triazolium Salts in Aqueous Solution was written by Massey, Richard S.;Collett, Christopher J.;Lindsay, Anita G.;Smith, Andrew D.;O’Donoghue, AnnMarie C.. And the article was included in Journal of the American Chemical Society in 2012.Electric Literature of C11H12BF4N3O The following contents are mentioned in the article:
Second-order rate constants have been determined for deuteroxide ion-catalyzed exchange of the C(3)-proton for deuterium, kDO (M-1 s-1), of a series of 20 triazolium salts in aqueous solution at 25 °C and ionic strength I = 1.0 (KCl). Evidence is presented that the rate constant for the reverse protonation of the triazol-3-ylidenes by solvent water is close to that for dielec. relaxation of solvent (1011 s-1). These data enabled the calculation of carbon acid pKa values in the range 16.5-18.5 for the 20 triazolium salts. PD rate profiles for deuterium exchange of the triazolium salts reveal that protonation at nitrogen to give dicationic triazolium species occurs under acidic conditions, with estimates of pKaN1 = -0.2 to 0.5. This study involved multiple reactions and reactants, such as 2-Phenyl-5,6-dihydro-8H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1414773-56-0Electric Literature of C11H12BF4N3O).
2-Phenyl-5,6-dihydro-8H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate (cas: 1414773-56-0) belongs to triazole derivatives. However, triazoles are also useful in bioorthogonal chemistry, because the large number of nitrogen atoms causes triazoles to react similar to azides. Triazole growth retardants such as uniconazole and paclobutrazol have been known to inhibit the biosynthesis of gibberellins by blocking kaurene oxidase, an P450 enzymeElectric Literature of C11H12BF4N3O
Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics