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From Bis(imidazol‐2‐yl)methanes to Asymmetrically Substituted Bis(heterocyclo)methanides in Metal Coordination
Author(s) -
Dauer DavidR.,
Koehne Ingo,
HerbstIrmer Regine,
Stalke Dietmar
Publication year - 2017
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.201601470
Subject(s) - chemistry , deprotonation , context (archaeology) , ligand (biochemistry) , metal , stereochemistry , coordination complex , nuclear magnetic resonance spectroscopy , benzothiazole , medicinal chemistry , crystal structure , crystallography , organic chemistry , ion , paleontology , biochemistry , receptor , biology
As an extension to the known symmetric bis(heterocyclo)methanes containing two identical heterocycles, new asymmetric ligand systems, based on benzoxazole, benzothiazole and 1‐methylbenzimidazole, are presented. Furthermore, the syntheses and reactions of two new symmetrically substituted methane derivatives, containing either 1‐methylimidazole or 1‐methylbenzimidazole, are discussed. In this context, firstly, (1‐MeNCNC 2 H 2 ) 2 CH 2 and (1‐MeNCNC 6 H 4 ) 2 CH 2 , and secondly, (NCSC 6 H 4 )CH 2 (NCOC 6 H 4 ) and (NCSC 6 H 4 )CH 2 (1‐MeNCNC 6 H 4 ), are used as parent compounds. They can be easily deprotonated at the central methylene bridge to generate a monoanionic structure akin to NacNac, so that the following complexes can be obtained: [Me 2 Al{(1‐MeNCNC 2 H 2 ) 2 CH}], [Me 2 Al{(1‐MeNCNC 6 H 4 ) 2 CH}], [Me 2 Al{(NCSC 6 H 4 )CH(NCOC 6 H 4 )}], [Me 2 Ga{(NCSC 6 H 4 )CH(NCOC 6 H 4 )}], [Me 2 Al{(NCSC 6 H 4 )CH(1‐MeNCNC 6 H 4 )}], [(THF) 2 Li{(1‐MeNCNC 6 H 4 ) 2 CH}] and [(diox) 2 Li{(NCSC 6 H 4 )CH(1‐MeNCNC 6 H 4 )}]. These compounds have been fully characterised by single‐crystal X‐ray diffraction (in the solid state) and NMR spectroscopy (in solution).