High Energy Chemistry

, Volume 47, Issue 4, pp 171–176 | Cite as

Specifics of photoinduced excited-state intramolecular proton transfer in o-tosylaminobenzoic and o-acetylaminobenzoic acids

  • M. N. Khimich
  • L. D. Uzhinova
  • L. D. Popov
  • A. S. Burlov
  • B. M. Uzhinov
Photochemistry

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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Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • M. N. Khimich
    • 1
  • L. D. Uzhinova
    • 1
  • L. D. Popov
    • 2
  • A. S. Burlov
    • 2
  • B. M. Uzhinov
    • 1
  1. 1.Moscow State UniversityMoscowRussia
  2. 2.South Federal UniversityRostov-on-DonRussia

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