Journal of the Chemical Society - Faraday Transactions p. 2239 - 2244 (1996)
Update date:2022-08-16
Topics:
Carmona, Carmen
Balon, Manuel
Munoz, Maria A.
Guardado, Pilar
Steady-state and time-resolved fluorescence measurements of THHN (9H-1-methyl-1,2,3,4-tetrahydropyrido[3,4-b]indole), have been carried out as a function of the acidity or basicity of the medium. In these media, four different THHN species have been detected, namely: dication (DC), cation (C), neutral (N) and anion (A). Attempts have been made to determine the excited state pKa* values for the three prototropic processes: N-A, C-N and DC-C reactions. The dicationic and anionic forms, observed outside the 0-14 pH range, are extremely weakly fluorescent species and only the second-order rate constants for the protonation and deprotonation processes, respectively, could be determined. In the case of the C-N process, studied in near-neutral media, excited-state proton exchange is much slower than fluorescence emission and the inflection points in the fluorimetric titration curves correspond quite closely to the ground state pKaG.
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