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Proton-induced supramolecular dimerization of aminomethylbenzo-15-crown-5 accompanied by a covalent dimerization of cyanoborohydride anion
Authors:Olga P KryatovaIvan V Korendovych  Elena V Rybak-Akimova
Institution:Department of Chemistry, Tufts University, Medford, MA 02155, USA
Abstract:Reductive amination of 4′-formylbenzo-15-crown-5] with sodium cyanoborohydride in the NH4Ac/MeOH medium followed by acid addition and extraction with CHCl3 unexpectedly lead to the isolation of the salt (B15C5-CH2-NH3)+-(H3BCNBH2CN) with an unusual dicyanodiborohydride anion. The self-complementary 4′-ammoniomethylbenzo-15-crown-5] cation was found to exist as a supramolecular dimer in the solid state, acetonitrile solution, and gas phase as revealed by X-ray crystallography, NMR and mass spectrometry, respectively.
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