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Issue 22, 2003
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Structure, modelling and dynamic behaviour of aza- and azaoxamacrocyclic ligands derived from (R,R)-1,2-diaminocyclohexane

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Abstract

Investigations into the conformational behaviour of macrocyclic ligands 5 and 6 derived from (R,R)-1,2-diaminocyclohexane have been undertaken using molecular modelling, single crystal X-ray diffraction and variable temperature 1H NMR spectroscopy. These have revealed that the lowest energy conformers in both cases do not possess the expected C2-element of symmetry, which can only be accessed at higher temperatures. Instead both molecules exist as C1-conformers at room temperature and in the solid state. In solution a range of dynamic exchange processes is observed which result, in part from the inherent strain in these fused bicyclic systems. An unexpected but characteristic feature of the C1-symmetric conformers is highlighted by the presence of a signal at unexpectedly low field in their 1H NMR spectra due to the interaction of two of the sulfonyl oxygen atoms with one of the bridgehead hydrogen atoms.

Graphical abstract: Structure, modelling and dynamic behaviour of aza- and azaoxamacrocyclic ligands derived from (R,R)-1,2-diaminocyclohexane

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Article information


Submitted
23 Jun 2003
Accepted
09 Sep 2003
First published
02 Oct 2003

Org. Biomol. Chem., 2003,1, 4058-4063
Article type
Paper

Structure, modelling and dynamic behaviour of aza- and azaoxamacrocyclic ligands derived from (R,R)-1,2-diaminocyclohexane

S. Pulacchini, R. Nasser, K. F. Sibbons, M. Motevalli, G. E. Hawkes, R. T. Kroemer, E. S. Bento and M. Watkinson, Org. Biomol. Chem., 2003, 1, 4058
DOI: 10.1039/B306963J

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