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Complexes of TETROL with selected heterocyclics: unconventional host–guest hydrogen bonding and the correlation with host selectivity

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Abstract

Here we investigate and compare the more salient characteristics of host–guest complexes of (+)-(2R,3R)-1,1-4,4-tetraphenylbutane-1,2,3,4-tetraol (TETROL) with four heterocyclic guests, morpholine, piperidine, pyridine and dioxane. These guests each formed inclusion compounds with TETROL, and host:guest ratios were either 1:2 or 1:1. Single crystal diffraction experiments revealed unprecedented host behaviour in the presence of both piperidine and dioxane with respect to the mode of host–guest hydrogen bonding employed. Furthermore, by utilizing 1H-NMR spectroscopy or gas chromatography (as applicable) as methods for analysing complexes obtained from competition experiments, we were able to identify the host selectivity order, and were gratified to discover that this order correlated precisely with host–guest hydrogen bond distance.

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Acknowledgements

Financial support is acknowledged from the Nelson Mandela University and the National Research Foundation. Prof. Mino Caira (University of Cape Town) is thanked for fruitful hydrogen bond discussions.

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Authors and Affiliations

  1. Department of Chemistry, Nelson Mandela University, PO Box 77000, Port Elizabeth, 6031, South Africa

    Benita Barton, Sasha-Lee Dorfling & Eric C. Hosten

Authors
  1. Benita Barton
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  2. Sasha-Lee Dorfling
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  3. Eric C. Hosten
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Correspondence to Benita Barton.

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Barton, B., Dorfling, SL. & Hosten, E.C. Complexes of TETROL with selected heterocyclics: unconventional host–guest hydrogen bonding and the correlation with host selectivity. J Incl Phenom Macrocycl Chem 92, 251–259 (2018). https://doi.org/10.1007/s10847-018-0840-y

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