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Structure and Bonding of Tetracyanopyrrolides
Author(s) -
Becker Martin,
Harloff Jörg,
Jantz Thomas,
Schulz Axel,
Villinger Alexander
Publication year - 2012
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201200790
Subject(s) - chemistry , delocalized electron , lone pair , ionic bonding , ring (chemistry) , ion , non covalent interactions , ligand (biochemistry) , atom (system on chip) , nitrogen atom , crystallography , hydrogen bond , molecule , organic chemistry , biochemistry , receptor , computer science , embedded system
Salts bearing the tetracyanopyrrolide anion (TCP) were synthesized from tetracyano‐1,4‐dithiin and sodium azide according to a modified synthetic protocol. The solid‐state structures of HTCP, MeTCP, Me 4 NTCP, NaTCP, and the ionic liquid EMIMTCP (EMIM = 1‐ethyl‐3‐methylimidazolium) are discussed for the first time. According to experimental and computational data, the TCP anion can be regarded as a pseudohalide with π bonds highly delocalized over the entire anion including the four cyano groups. The planar anion is C 2 v symmetric and represents a multifunctional binary CN ligand, which is capable of forming classic coordination bonds through the lone pairs of the CN groups or the ring nitrogen atom. In addition, noncovalent interactions such as π–π interactions are found and can be used to strengthen structural and electronic communication between organic ligands.