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首页> 外文期刊>The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory >On the Mechanism of Alcohol-Catalyzed Excited-State Intramolecular Proton Transfer in Cationic Benzimidazoles
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On the Mechanism of Alcohol-Catalyzed Excited-State Intramolecular Proton Transfer in Cationic Benzimidazoles

机译：阳离子苯并咪唑中醇催化激发态分子内质子转移的机理

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摘要

The ground- and excited-state behavior of the monocations of 2-(6'-hydroxy-2'-pyridyl)benzimidazole (1) and 1-methyl-2-(6'-hydroxy-2'-pyridyl)benzimidazole (2) is discussed. Excited-state proton transfer from the hydroxyl group to the pyridyl nitrogen occurs in compounds 1 and 2 acidified acetonitrile solutions by the assistance of an alcohol. We propose a model for the mechanism of this proton-transfer process which includes a concerted biprotonic or multiprotonic transfer with one or two alcohol molecules. Essential for the occurrence of the proton transfer is the presence of a quencher with hydrogen-bond donating and accepting properties. Furthermore, it is shown that also the size and geometry of the quencher play a role in the efficiency of the proton-transfer process. Compounds 1 and 2 differ remarkably in the efficiency of this process as a result of the presence of the methyl group on the benzimidazole nitrogen N(1) in compound 2.
机译：2-（6'-羟基-2'-吡啶基）苯并咪唑（1）和1-甲基-2-（6'-羟基-2'-吡啶基）苯并咪唑（2）的单阳离子的基态和激发态行为）进行了讨论。在醇协助下，在化合物1和2酸化的乙腈溶液中发生从质子到羟基的激发态质子转移。我们为这种质子转移过程的机制提出了一个模型，该模型包括一个或两个醇分子的协同双质子或多质子转移。质子转移发生的必要条件是存在具有氢键给予和接受性质的淬灭剂。此外，已经表明，淬灭剂的尺寸和几何形状也在质子转移过程的效率中起作用。由于化合物2中苯并咪唑氮N（1）上存在甲基，因此化合物1和2在此过程的效率上有显着差异。

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