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

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• 作者：M. N. Khimich (17402)
  L. D. Uzhinova (17402)
  L. D. Popov (27402)
  A. S. Burlov (27402)
  B. M. Uzhinov (17402)
  
• 刊名：High Energy Chemistry
• 出版年：2013
• 出版时间：July 2013
• 年：2013
• 卷：47
• 期：4
• 页码：171-176
• 全文大小：194KB
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• 作者单位：M. N. Khimich (17402)
  L. D. Uzhinova (17402)
  L. D. Popov (27402)
  A. S. Burlov (27402)
  B. M. Uzhinov (17402)
  
  17402. Moscow State University, Moscow, 119991, Russia
  27402. South Federal University, ul. Bol鈥檚haya Sadovaya 105/42, Rostov-on-Don, 344090, Russia
  

文摘

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.