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Preparation and Intramolecular CC Coupling Reaction for Bis‐benzimidazolium Salt
Author(s) -
Liu Rui,
Huo Ran,
Bi Yue,
Zhao Zhixiang,
Liu Qingxiang
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500375
Subject(s) - chemistry , intramolecular force , hydrogen bond , supramolecular chemistry , double bond , crystallography , salt (chemistry) , coupling reaction , crystal structure , catalysis , proton nmr , stereochemistry , polymer chemistry , molecule , organic chemistry
Bis‐benzimidazolium salt 1 was prepared via a series of reactions using 2,2′‐diphenol as starting material. Compound 2 was afforded through the intramolecular CC coupling reaction of 1 under the catalysis of Pd(OAc) 2 . The structure of 2 is characterized through X‐ray diffraction analyses, 1 H NMR and 13 C NMR. In 2 , two boat‐like seven‐membered rings are contained, where the CC bond distance newly formed is 1.461(5) Å, and it is between regular CC single bond (1.54 Å) and CC double bond (1.34 Å). This shows that new CC bond has partial double‐bond character. In the crystal packing of 2 , the 2D supramolecular layers are formed via CH···F hydrogen bond.