吲哚类化合物在杂环化学中占有重要地位。随着含有吲哚基功能团的有机功能分子的不断涌现，它们的性质研究已成为一项具有挑战性的工作。本项目拟选用具有代表性结构的3-取代吲哚类化合物为研究对象，采用电喷雾串联质谱技术，结合同位素标记、准确分子量测量、理论计算等手段，系统研究其在各种阳离子诱导下的裂解反应，提取其气相“H/D scrambling”现象。考察取代基、阳离子种类以及解离活化方式对该现象的影响，揭示其反应机理和规律，建立通用性“H/D scrambling”模型。本项目的开展不仅丰富了气相离子化学的研究内容，而且可以为该类型化合物激发态中的分子内质子转移反应提供新思路。

Indole derivatives play an important role in heterocyclic chemistry. With the development of new organic functional molecules containing indole substructures, it is challenging to evaluate their physicochemical property. In this project, the ‘H/D scrambling’phenomenon in the fragmentation reactions of 3-substitued indoles induced by different cations will be explored systematically by a combination of electrospray ionization tandem mass spectrometry, isotopic labeling, accurate molecular weight measurement and theoretical calculations. Several factors related to this phenomenon, such as kinds of substituent group and cation, the induced modes of dissociation will be investigated. As a result , the mechanisms and general rules for ‘H/D scrambling’would be demonstrated. Accomplishment of this project not only enriches the contents of gas phase ion chemistry, it also provides potential ideas for intramolecular proton transfer in excited-state molecules.