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 BartonEmail author
  • Eric C. Hosten
  • Pieter L. Pohl
Original Article


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.


Host–guest chemistry Inclusion Complexes Selectivity Nitrobenzene Nitrotoluene 



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

Supplementary material

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  1. 1.
    Bikelytė, G., Härtel, M., Stierstorfer, J., Klapötke, T.M., Pimerzin, A.A., Verevkin, S.P.: Benchmark properties of 2-, 3- and 4- nitrotoluene: evaluation of thermochemical data with complementary experimental and computational methods. J. Chem. Thermodyn. 111(Supplement C), 271–278 (2017)Google Scholar
  2. 2.
    Wang, B., Wu, Y., Jiang, B., Song, H., Li, W., Jiang, Y., Wang, C., Sun, L., Li, Q., Li, A.: Optimized degradation removal of 2-nitrotoluene by combination of cathodic reduction and electro-oxidation process. Electrochim. Acta 219(Supplement C), 509–515 (2016)CrossRefGoogle Scholar
  3. 3.
    Sangeetha, K., Guru Prasad, L., Mathammal, R.: Structural elucidation and physicochemical properties of an organic NLO crystal: 4-nitrotoluene-2-sulphonic acid dihydrate. J. Mol. Struct. 1155, 598–609 (2018)CrossRefGoogle Scholar
  4. 4.
    Kumar, A., Kumar, P., Paul, S., Jain, S.L.: Visible light assisted reduction of nitrobenzenes using Fe(bpy)3 + 2/rGO nanocomposite as photocatalyst. Appl. Surf. Sci. 386(Supplement C), 103–114 (2016)CrossRefGoogle Scholar
  5. 5.
    Sharma, D., Mishra, S.: Chemical reactivity of coal under Friedel-Crafts reaction conditions: effect of nature of solvent, alkylating agent and catalyst on extractability of coal through a complex series reaction (ATD 3 reaction). Fuel 74, 913 (1995)CrossRefGoogle Scholar
  6. 6.
    Sun, Z., Hu, P., Ma, M., Li, L.: Lanthanide organic frameworks for luminescence sensing of nitrobenzene and nitrophenol with high selectivity. Dyes Pigments 143, 10–17 (2017)CrossRefGoogle Scholar
  7. 7.
    Mondal, S., Das, N.: Synthesis of triptycene based non-conjugated polytriazole: temperature dependent regioselectivity and host–guest interaction with nitroaromatics. Polymer 75, 109–118 (2015)CrossRefGoogle Scholar
  8. 8.
    Bagul, R.S., Rajesh, Y.B.R.D., Jayamurugan, G., Bera, A., Sood, A.K., Jayaraman, N.: Photophysical behavior of poly(propyl ether imine) dendrimer in the presence of nitroaromatic compounds. J. Photochem. Photobiol. A 253, 1–6 (2013)CrossRefGoogle Scholar
  9. 9.
    Barton, B., Hosten, E.C., Pohl, P.L.: Discrimination between o-xylene, m-xylene, p-xylene and ethylbenzene by host compound (R,R)-(–)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol. Tetrahedron 72, 8099–8105 (2016)CrossRefGoogle Scholar
  10. 10.
    Barton, B., Hosten, E.C., Pohl, P.L.: Host (–)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol and guests aniline, N-methylaniline and N,N-dimethylaniline: a selectivity study. Aust. J. Chem. 71, 133–141 (2018)CrossRefGoogle Scholar
  11. 11.
    Barton, B., Dorfling, S.-L., Hosten, E.C., Pohl, P.L.: Host compounds (+)-(2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol (TETROL) and (2R,3R)-(–)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) with guests o-, m- and p- toluidine: a comparative investigation. Tetrahedron 74, 2754–2761 (2018)CrossRefGoogle Scholar
  12. 12.
    Barton, B., Caira, M.R., Hosten, E.C., McCleland, C.W.: A computational, X-ray crystallographic, and thermal stability analysis of TETROL and its pyridine and methylpyridine inclusion complexes. Tetrahedron 69, 8713–8723 (2013)CrossRefGoogle Scholar
  13. 13.
    Bruker, A.X.S.: APEX2, SADABS and SAINT. Bruker AXS, Madison (2010)Google Scholar
  14. 14.
    Sheldrick, G.M.: SHELXT-integrated space-group and crystal structure determination. Acta Crystallogr. C71, 3–8 (2015)Google Scholar
  15. 15.
    Hübschle, C.B., Sheldrick, G.M., Dittrich, B.: ShelXle: a Qt graphical user interface for SHELXL. J. Appl. Crystallogr. 44, 1281–1284 (2011)CrossRefGoogle Scholar
  16. 16.
    Shan, Z., Hu, X., Zhou, Y., Peng, X., Li, Z.: A convenient approach to C2-chiral 1,1,4,4-tetrasubstituted butanetetraols: direct alkylation or arylation of enantiomerically pure diethyl tartrates. Helv. Chim. Acta 93, 497–503 (2010)CrossRefGoogle Scholar
  17. 17.
    Toda, F., Tanaka, K., Stein, Z., Goldberg, I.: Structure and inclusion characteristics of (R,R)-(–)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol. J. Chem. Soc. Perkin Trans. 2, 2359–2361 (1993)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  1. 1.Department of ChemistryNelson Mandela UniversityPort ElizabethSouth Africa

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