Specifics of photoinduced excited-state intramolecular proton transfer in o-tosylaminobenzoic and o-acetylaminobenzoic acids |
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Authors: | M. N. Khimich L. D. Uzhinova L. D. Popov A. S. Burlov B. M. Uzhinov |
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Affiliation: | 17402. Moscow State University, Moscow, 119991, Russia 27402. South Federal University, ul. Bol’shaya Sadovaya 105/42, Rostov-on-Don, 344090, Russia
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Abstract: | 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. |
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