Issue 43, 2020

Selective enclathration of xylenols: synergistic effects of mixed hosts

Abstract

The six xylenol (XYL) isomers can be separated by selective enclathration with the host 4,4-isopropylidene bisphenol, H1. Crystal structures were elucidated for the following single and mixed guest inclusion compounds with H1: H1·34XYL (I), H1·35XYL (II), H1·23XYL·26XYL (III), H1·23XYL·35XYL (IV), where the xylenol isomers are abbreviated as, for example 34XYL for 3,4-xylenol. The crystal structures of selected H1·xylenols showed that there is extensive host⋯host and host⋯guest hydrogen bonding. Competition experiments with equimolar mixtures of pairs of xylenols (XYL) showed that the preference for inclusion was in the sequence 34XYL > 35XYL > 26XYL > 23XYL > 25XYL > 24XYL. By analogy to the Dutch resolution method (in which families of resolving agents are used to achieve chiral separations), two host compounds similar to H1 were used in pairs with H1 to improve the selectivity of the xylenols. 4,4′-(9-Fluorenylidene)bisphenol, H2, and 4,4′(cyclohexylidene)bisphenol, H3, were used in pairs with H1 and were shown to enhance the selectivity of a given xylenol which had been poorly separated by H1 alone. The crystal structure was elucidated for an unusual mixed host–mixed guest inclusion compound, H1·H2·26XYL/35XYL (V).

Graphical abstract: Selective enclathration of xylenols: synergistic effects of mixed hosts

Supplementary files

Article information

Article type
Paper
Submitted
03 Apr. 2020
Accepted
22 Jūn. 2020
First published
22 Jūn. 2020

CrystEngComm, 2020,22, 7389-7398

Selective enclathration of xylenols: synergistic effects of mixed hosts

J. S. Bouanga Boudiombo, H. Su, N. Ravenscroft, S. A. Bourne and L. R. Nassimbeni, CrystEngComm, 2020, 22, 7389 DOI: 10.1039/D0CE00510J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements