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

  • Benita BartonEmail author
  • Sasha-Lee Dorfling
  • Eric C. Hosten
Original Article


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.


Host–guest chemistry Complexes Selectivity Hydrogen bonding TETROL 



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.

Supplementary material

10847_2018_840_MOESM1_ESM.docx (363 kb)
Supplementary material 1 (DOCX 362 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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