Department of Chemistry, Organic Chemistry, University of Cologne, Greinstrasse 4, 50939, Cologne, Germany.
Institute of Chemistry, Technical University Berlin, Straße des 17. Juni 115, 10623, Berlin, Germany.
Chemistry. 2019 Feb 18;25(10):2511-2518. doi: 10.1002/chem.201803641. Epub 2019 Jan 17.
N-Heterocyclic carbenes (NHCs, :C) can interact with azolium salts (C-H ) by either forming a hydrogen-bonded aggregate (CHC ) or a covalent C-C bond (CCH ). In this study, the intramolecular NHC-azolium salt interactions of aromatic imidazolin-2-ylidenes and saturated imidazolidin-2-ylidenes have been investigated in the gas phase by traveling wave ion mobility mass spectrometry (TW IMS) and DFT calculations. The TW IMS experiments provided evidence for the formation of these important intermediates in the gas phase, and they identified the predominant aggregation mode (hydrogen bond vs. covalent C-C) as a function of the nature of the interacting carbene-azolium pairs.
N-杂环卡宾（NHCs，:C）可以通过形成氢键聚集体（CHC）或共价 C-C 键（CCH）与唑鎓盐（C-H）相互作用。在这项研究中，通过飞行时间离子迁移质谱（TW IMS）和 DFT 计算研究了芳基咪唑啉-2-亚基和饱和咪唑啉-2-亚基的分子内 NHC-唑鎓盐相互作用。TW IMS 实验提供了这些重要中间体在气相中形成的证据，它们确定了主要的聚集模式（氢键与共价 C-C）作为相互作用的卡宾-唑鎓对的性质的函数。
