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Four xanthenyl-derived compounds: a comparative investigation of their host behaviour in the presence potential saturated and unsaturated heterocyclic six-membered ring guest solvents

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Abstract

Four xanthenyl-derived host compounds, namely trans-N,N′-bis(9-phenyl-9-xanthenyl)cyclohexane-1,4-diamine (1,4-DAX), trans-N,N′-bis(9-phenyl-9-thioxanthenyl)cyclohexane-1,4-diamine (1,4-DAT), N,N′-bis(9-cyclohexyl-9-xanthenyl)ethylenediamine (OED) and N,N′-bis(9-cyclohexyl-9-thioxanthenyl)ethylenediamine (SED) were assessed for their selectivity behaviour in the presence of both the saturated and unsaturated heterocyclic six-membered ring guest solvents morpholine (MOR), piperidine (PIP), dioxane (DIO) and pyridine (PYR). Related compounds OED and SED behaved similarly when each was recrystallized from mixtures of these guests, both selecting for MOR and discriminating against PYR, while, surprisingly, the performance of structurally-similar 1,4-DAX and 1,4-DAT in equivalent conditions, on the other hand, was entirely contrasting: only 1,4-DAX formed complexes from such guest mixtures and 1,4-DAT failed to do so in each instance. Furthermore, 1,4-DAX preferred PYR, an observation distinct from that of OED and SED. Single crystal diffraction (SCXRD) experiments were carried out on suitable crystals formed by 1,4-DAX with these guests, and it was revealed that the preference for PYR may be attributed to both host–guest π–π interactions and a shorter H-bond between molecules of the host and PYR compared with other complexes. SCXRD experiments were not possible for OED, SED and 1,4-DAT owing to either the inability of the host compound to complex with these guests or poor crystal quality of the resultant complexes.

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Acknowledgements

Financial support is acknowledged from the Nelson Mandela University and the National Research Foundation (NRF).

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Authors and Affiliations

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

    Benita Barton, Daniel V. Jooste, Ulrich Senekal & Eric C. Hosten

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  1. Benita Barton
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  2. Daniel V. Jooste
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  3. Ulrich Senekal
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  4. Eric C. Hosten
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Correspondence to Benita Barton.

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Electronic supplementary material

The crystallographic data for all complexes where suitable crystal quality was obtained were deposited at the Cambridge Crystallographic Data Centre {CCDC-1964563 [1,4-DAX•2(PYR)], 1964564 [1,4-DAX•2(DIO)], 1964565 [1,4-DAX•2(MOR)], 1964566 [1,4-DAX•2(PIP)], 1964567 [1,4-DAT•2(DIO)], 1918458 (OED•PYR) and 1918461 (SED•PYR). These data may be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif. A comprehensive table displaying the H⋯G and G⋯G interactions is provided in Table S1, and additional figures illustrating the classical intermolecular H-bonding interactions between 1,4-DAX and PIP (Figure S1a) and MOR (Figure S1b) may also be found here. Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 303 kb)

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Barton, B., Jooste, D.V., Senekal, U. et al. Four xanthenyl-derived compounds: a comparative investigation of their host behaviour in the presence potential saturated and unsaturated heterocyclic six-membered ring guest solvents. J Incl Phenom Macrocycl Chem 97, 217–229 (2020). https://doi.org/10.1007/s10847-020-00997-w

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