Proton-induced supramolecular dimerization of aminomethylbenzo-15-crown-5 accompanied by a covalent dimerization of cyanoborohydride anion

Olga P. Kryatova, Ivan V. Korendovych, Elena V. Rybak-Akimova

Research output: Contribution to journalArticle

9 Scopus citations

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)+-(H 3BCNBH2CN)- 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.

Original languageEnglish (US)
Pages (from-to)4251-4255
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number22
DOIs
StatePublished - May 26 2003
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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