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Halides with fifteen aliphatic C-H···Anion interaction sites

Shi, Genggongwo, Aliakbar Tehrani, Zahra, Kim, Dongwook, Cho, Woo Jong, Youn, Il-Seung, Lee, Han Myoung, Yousuf, Muhammad, Ahmed, Nisar, Shirinfar, Bahareh, Teator, Aaron J., Lastovickova, Dominika N., Rasheed, Lubna, Lah, Myoung Soo, Bielawski, Christopher W. and Kim, Kwang S. 2016. Halides with fifteen aliphatic C-H···Anion interaction sites. Scientific Reports 6 (1) , 30123. 10.1038/srep30123

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Abstract

Since the aliphatic C–H···anion interaction is relatively weak, anion binding using hydrophobic aliphatic C–H (Cali–H) groups has generally been considered not possible without the presence of additional binding sites that contain stronger interactions to the anion. Herein, we report X-ray structures of organic crystals that feature a chloride anion bound exclusively by hydrophobic Cali–H groups. An X-ray structure of imidazolium-based scaffolds using Cali–H···A− interactions (A− = anion) shows that a halide anion is directly interacting with fifteen Cali–H groups (involving eleven hydrogen bonds, two bidentate hydrogen-bond-type binding interactions and two weakly hydrogen-bonding-like binding interactions). Additional supporting interactions and/or other binding sites are not observed. We note that such types of complexes may not be rare since such high numbers of binding sites for an anion are also found in analogous tetraalkylammonium complexes. The Cali–H···A− interactions are driven by the formation of a near-spherical dipole layer shell structure around the anion. The alternating layers of electrostatic charge around the anion arise because the repulsions between weakly positively charged H atoms are reduced by the presence of the weakly negatively charged C atoms connected to H atoms.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Nature Publishing Group
ISSN: 2045-2322
Date of First Compliant Deposit: 8 May 2017
Date of Acceptance: 27 June 2016
Last Modified: 04 Jun 2017 09:49
URI: http://orca.cardiff.ac.uk/id/eprint/100414

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