Proton-induced supramolecular dimerization of aminomethylbenzo-15-crown-5 accompanied by a covalent dimerization of cyanoborohydride anion |
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Authors: | Olga P KryatovaIvan V Korendovych Elena V Rybak-Akimova |
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Affiliation: | Department of Chemistry, Tufts University, Medford, MA 02155, USA |
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Abstract: | Reductive amination of 4′-formyl[benzo-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′-ammoniomethyl[benzo-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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