Stereoselectivity in complexation of primary alkylammonium cations by the diastereotopic faces of chiral asymmetric crowns

Dale A. Laidler, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

The temperature-dependent 1H n.m.r. spectra of the 1:1 complexes formed between crowns D-(1), DD-(2), D-(3), and DD-(4) and primary alkylammonium cations in solution are interpreted in terms of equilibria involving diastereoisomeric complexes of (i) similar strengths in the case of the galacto-crowns D-(1) and DD-(2) and (ii) dissimilar strengths in the case of the gluco-crowns D-(3) and DD-(4) where a secondary interaction of a dipole-induced dipole type appears to be responsible for the stereoselectivity.

Original languageEnglish (US)
Pages (from-to)481-483
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Issue number14
DOIs
StatePublished - 1977

ASJC Scopus subject areas

  • Molecular Medicine

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