Journal of the American Chemical Society p. 3956 - 3963 (1985)
Update date:2022-08-16
Topics:
Shizuka, Haruo
Kameta, Kosei
Shinozaki, Tsutomu
Proton-transfer reactions in the excited singlet state of naphthylammonium ion-18-crown-6 complexes in MeOH-H2O (9:1) mixtures have been studied by means of the single photon counting method with fluorimetry.It is found that the complex formation of naphthylammonium ions with 18-crown-6 decreases markedly the proton-transfer rate (k1) in the excited state, resulting in an increase of its lifetime.The back protonation rate in the excited state is negligibly small compared with those of the other decay processes; there is no excited-state prototropic equilibrium in the naphthylammonium ion-crown complexes (RN(1+)H3-crown).The one-way proton transfer reaction is elucidated by the presence of the excited neutral amine-crown complex (RNH2-crown)* produced by deprotonation of (RN(1+)H3-crown)*, where protonation to the amino group is structurally blocked by 18-crown-6 and the naphthyl group (R) of the complex.However, proton-induced quenching (k'q) occurs effectively especially in the 1-naphthylammonium ion-crown complex.The ground-state association constants (Kg) of the complexes can be determined easily by the fluorescence titration method.Temperature effects upon the excited-state proton-transfer reactions of the complexes have been also carried out in order to study their thermodynamic properties.A Corey-Pauling-Kolton model of the anilinium ion-18-crown-6 complex proposed by Izatt et al. is strongly supported by the present work.
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