Abstract
AbstractThe excited‐state proton transfer (ESPT) of the strong photoacid, N‐methyl‐7‐hydroxyquinolium (NM7HQ+), was studied in the presence of N‐methylbenzamide (NMB) as a base in the aprotic polar solvent, acetonitrile. According to the Benesi–Hildebrand relation, it was revealed that the hydrogen (H)‐bonded complex of NM7HQ+ and NMB exists in the ground state in a 1:1 stoichiometry with the association constant of 22.2 ± 1.7 M−1. The fluorescence quenching of the 1:1 complex was observed to follow the Stern–Volmer relation with the molecularity of one for NMB indicating that the ESPT of NM7HQ+ occurs with the H‐bonded chain of two NMB molecules. Our study highlights the cooperative nature of H‐bonding in the chemical reactivity of amide in acid–base reactions as has already been reported for alcohol.
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