Citation: XIANG Jun-Feng, YI Ping-Gui, REN Zhi-Yong, YU Xian-Yong, CHEN Jian, LIU Wu, LI Tao-Mei. Effect of Supra-Molecular Interaction on the Intramolecular Proton Transfer of 2-(2-Aminophenyl)benzothiazole[J]. Acta Physico-Chimica Sinica, ;2016, 32(3): 624-630. doi: 10.3866/PKU.WHXB201512291 shu

Effect of Supra-Molecular Interaction on the Intramolecular Proton Transfer of 2-(2-Aminophenyl)benzothiazole

1.
Hunan Province College Key Laboratory of QSAR/QSPR, Key Laboratory of Theoretical Chemistry and Molecular Simulation, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, Hunan Province, P. R. China

Corresponding author: YI Ping-Gui,
Received Date: 28 August 2015
Available Online: 28 December 2015
Fund Project: 国家自然科学基金(21172066,20971041) (21172066,20971041)湖南省高校科技创新团队项目(湘教通[2012]318)资助 (湘教通[2012]318)

The excited-state intramolecular proton transfer of 2-(2-aminophenyl)benzothiazole (APBT) in different environments was detected by steady-state and transient fluorescence spectral measurements and quantum chemical calculations. The results showed that the polarity and protonation of the solution strongly affect the proton transfer of APBT. When APBT and cucurbit[7]uril (CB[7]) were mixed with each other, we found that the proton transfer process of APBT was restrained by the formation of a complex with a stoichiometric ratio of 1 : 1. The association constant and thermodynamic parameters of this complex were calculated. 1H NMR spectroscopy and quantum chemical calculation data indicated that a 1 : 1 APBT@CB[7] complex of the amine or imine tautomer of APBT formed.
- Proton transfer,
- Cucurbit[7]uril,
- Polarizable continuum model,
- Thermodynamics,
- Host-guest chemistry
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