Specifics of photoinduced excited-state intramolecular proton transfer in o-tosylaminobenzoic and o-acetylaminobenzoic acids
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- Khimich, M.N., Uzhinova, L.D., Popov, L.D. et al. High Energy Chem (2013) 47: 171. doi:10.1134/S0018143913040073
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In the ground state, o-tosylaminobenzoic and o-acetylaminobenzoic acids exist in the form of two rotamers with intramolecular hydrogen bonds N-H...O=C (cis) and N-H...O(OH)-C (trans). In nonpolar solvents, the formation of dimers with hydrogen bonding between carboxyl groups takes place. Efficient barrierless excited state intramolecular proton transfer (ESIPT) occurs along the N-H...O=C hydrogen bond upon excitation of o-tosylaminobenzoic acid. The efficiency of ESIPT in o-acetylaminobenzoic acid is lower because of the low acidity of the substituted amino group.