Issue 25, 2020

Effect of anions on the solid-state interplay of symmetric and unsymmetric phosphonium cations

Abstract

Eight organic salts made up of two different organic phosphonium monocations, tetraphenylphosphonium or benzyltriphenylphosphonium, and common anions of different shape, size and charge distribution have been structurally authenticated. The crystal packing for the tetraphenylphosphonium cations involves one-dimensional infinite stacked columns incorporating translational quadruple embraces (TQPE) regardless of the type of counter ion. As for benzyltriphenylphosphonium salts, different packing arrays were obtained with different anions. Interestingly, the anions control the intermolecular packing of the same phosphonium cation, while hydrogen bonding is found to be the dominant contributor in the overall self-assembly. Hydrophobic interactions between the phosphonium cations driven by the phenyl–phenyl embrace involving π⋯π and/or C–H⋯π interactions also contribute to the cohesion of the structures. Charge-assisted hydrogen bonding and halogen bonding were also evident, which are relatively strong compared to classical hydrogen bonds, as judged from the short intermolecular distances. The interactions have also been quantified using Hirshfeld surfaces analyses.

Graphical abstract: Effect of anions on the solid-state interplay of symmetric and unsymmetric phosphonium cations

Supplementary files

Article information

Article type
Paper
Submitted
20 Apr 2020
Accepted
21 May 2020
First published
02 Jun 2020

New J. Chem., 2020,44, 10220-10228

Effect of anions on the solid-state interplay of symmetric and unsymmetric phosphonium cations

I. Ling, B. W. Skelton, A. N. Sobolev, Y. Alias, Z. C. Khor and C. L. Raston, New J. Chem., 2020, 44, 10220 DOI: 10.1039/D0NJ01975E

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