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RESEARCH ARTICLE
Contents Vol 71(3)

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

Benita Barton A B , Eric C. Hosten A and Pieter L. Pohl A
+ Author Affiliations
- Author Affiliations

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

B Corresponding author. Email: benita.barton@nmmu.ac.za

Australian Journal of Chemistry 71(3) 133-141 https://doi.org/10.1071/CH17532
Submitted: 5 October 2017  Accepted: 2 November 2017   Published: 29 November 2017

Abstract

The compound (–)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) forms 2 : 1 host : guest complexes with aniline, N-methylaniline, and N,N-dimethylaniline when recrystallized from these solvents. When the guests competed, as in binary and ternary mixtures, DMT proved to be remarkably selective for the alkylated guests, discriminating consistently against aniline. A host selectivity order of aniline << N-methylaniline < N,N-dimethylaniline was observed. Results from single-crystal diffraction, Hirshfeld surface, and thermal analyses were used to explain the observed preference order. This investigation shows that using the realm of supramolecular chemistry may have future application in the separation of these anilines.


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