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Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates

Mumtaz, Salma; Cano, Israel; Mumtaz, Nargis; Abbas, Ahmed; Dupont, Jairton; Gondal, Humaira Yasmeen

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Authors

Salma Mumtaz

Israel Cano

Nargis Mumtaz

Ahmed Abbas

Jairton Dupont

Humaira Yasmeen Gondal



Abstract

A series of novel benzimidazolium-based non-racemic ionic liquids (ILs) was synthesized from low–cost chiral terpenoid alcohols and fully characterized by the use of a wide variety of techniques, such as DSC, ESI-MS, ATR FT-IR, polarimetry as well as 1H and 13C NMR spectroscopy. The ILs were investigated as chiral shift agents for the chiral recognition of racemic mixtures of Mosher’s acid potassium salt by 19F NMR spectroscopy, leading to high splitting values of the CF3 signal. Supramolecular interactions between salt and H–C2 of chiral benzimidazolium cation are responsible for the chiral recognition, as was demonstrated by experimental evidences. Indeed, the enantiomeric excess value of enantioenriched substrates depends mainly on the strength of the contact ion pairs.

Citation

Mumtaz, S., Cano, I., Mumtaz, N., Abbas, A., Dupont, J., & Gondal, H. Y. (2018). Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates. Physical Chemistry Chemical Physics, 20(32), 20821-20826. https://doi.org/10.1039/C8CP03881C

Journal Article Type Article
Acceptance Date Jul 23, 2018
Online Publication Date Jul 23, 2018
Publication Date Aug 28, 2018
Deposit Date Jul 31, 2018
Publicly Available Date Dec 11, 2018
Journal Physical Chemistry Chemical Physics
Print ISSN 1463-9076
Electronic ISSN 1463-9076
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 20
Issue 32
Pages 20821-20826
DOI https://doi.org/10.1039/C8CP03881C
Keywords Benzimidazolium–based ionic liquids ; Chiral ionic liquids ; Chiral recognition ; Chiral shift agent ; Mosher’s acid
Public URL https://nottingham-repository.worktribe.com/output/947560
Publisher URL https://pubs.rsc.org/en/content/articlelanding/2018/cp/c8cp03881c#!divAbstract

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