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DMT [(−)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol], a highly efficient host compound for nitroaromatic guests: selectivity, X-ray and thermal analyses

  • Benita Barton
  • Eric C. Hosten
  • Pieter L. Pohl
Original Article

Abstract

In this work, we reveal that the compound (−)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) is a highly efficient host material for nitroaromatics o-nitrotoluene (o-NT), m-nitrotoluene (m-NT), p-nitrotoluene (p-NT) and nitrobenzene (NB). Each of these guests was included with a 2:1 host:guest ratio. The host displayed selectivity for p-NT and NB when these guests were mixed in equimolar proportions with any one of the other guest solvents, and the host recrystallized from this binary mixture. A selectivity order for the host in these conditions was thus noted to be NB ≈ p-NT > o-NT > m-NT. Furthermore, guests were also mixed in non-equimolar proportions and the host behaviour analysed, the results of which were in accordance with observations from the equimolar studies. Additionally, an equimolar quaternary experiment of all four guests provided a somewhat adjusted host selectivity order [p-NT (39.9%) > NB (30.2%) > m-NT (17.1%) > o-NT (12.8%)]. Single crystal diffraction analyses of all four complexes showed the crystals to share the same host packing, and comparable host–guest interactions were observed in each. However, thermal analyses, both DSC and TG, showed that the preferred guests p-NT and NB formed complexes with increased relative thermal stabilities, and this observation correlated with the selective behaviour of the host in competition experiments.

Keywords

Host–guest chemistry Inclusion Complexes Selectivity Nitrobenzene Nitrotoluene 

Notes

Acknowledgements

Financial support is acknowledged from the Nelson Mandela University and the National Research Foundation. L. Bolo is thanked for thermal analyses.

Supplementary material

10847_2018_853_MOESM1_ESM.pdf (168 kb)
Supplementary material 1 (PDF 168 KB)
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Supplementary material 2 (PDF 162 KB)
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Supplementary material 3 (PDF 156 KB)
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Supplementary material 4 (PDF 156 KB)
10847_2018_853_MOESM5_ESM.pdf (156 kb)
Supplementary material 5 (PDF 156 KB)

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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  1. 1.Department of ChemistryNelson Mandela UniversityPort ElizabethSouth Africa

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