Dynamic 1H nuclear magnetic resonance spectroscopic studies of complexes formed between substituted ammonium cations and two chiral diaza-crown ethers incorporating asymmetric carbohydrate units

Marek Pietraszkiewicz*, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Two diaza-18-crown-6 derivatives (1) and (2), incorporating methyl 4,6-O-benzylidene- and methyl 4,6-O-[(S)-phenylethylidene]-x-D-mannopyranosidic residues, have been shown, by variabletemperature high-field 1H n.m.r. spectroscopy, to form strong anisometric 1:1 complexes with substituted ammonium cations in CD2CI2 solutions. Although there are a few examples of almost equally populated anisometric complexes, in most cases the major complex is associated with the β-face of the macrocyclic ring. Relevant thermodynamic data have been obtained from integration of appropriate signals in the low-temperature spectra. Approximate kinetic data have been evaluated using appropriate equations for site exchange between unequally populated sites.

Original languageEnglish (US)
Pages (from-to)1559-1562
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number10
DOIs
StatePublished - Jan 1 1985

ASJC Scopus subject areas

  • Chemistry(all)

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