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- W2021124724 abstract "Abstract The acid-base interaction of 2,3-dimethyl-6-phenylimidazo-[1,2-b]-1,2,4-triazine (DMPIT) in the ground and excited states was studied. The electronic structures of 6-phenylimidazo-[1,2-b]-1,2,4-triazine and its cations were calculated by the CNDO/S and MNDO methods. The ground state protonation of the DMPIT molecule proceeds at the N5 atom of the imidazole ring. In hydrocarbon solvents, a hydrogen-bonded 1 : 1 complex and 1 : 2 ionic pair of DMPIT with trifluoroacetic acid are formed. In polar and basic solvents, a 1 : 1 ionic pair is formed (pKa=2.76). On excitation of DMPIT, the basicity of the N5 atom decreases ( p K a ∗ =−0.88 ) and that of the N4 atom increases. In the excited state, the dissociation of N5-protonated DMPIT takes place. The rate of dissociation increases as the solvent basicity increases. This reaction induces a radiationless deactivation (quantum yield of adiabatic reaction fr=0.46 in water). In dioxan, ethanol and water, excited DMPIT is protonated by an acid at the N4 atom by a dynamic mechanism. In hydrocarbon solvents, the phototautomerization of the N5 cation to the N4 cation takes place in the hydrogen-bonded 1 : 2 ionic pair. This photoreaction is similar to that in the 7-azaindole-solvent complex." @default.
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- W2021124724 date "1995-05-01" @default.
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- W2021124724 title "Acid-base interaction of 2,3-dimethyl-6-phenylimidazo-[1,2-b]-1,2,4-triazine in the ground and excited states" @default.
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