Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates
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 investi...
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| Format: | Article |
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Royal Society of Chemistry
2018
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| Online Access: | https://eprints.nottingham.ac.uk/53197/ |
| _version_ | 1848798899798540288 |
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| author | Mumtaz, Salma Cano, Israel Mumtaz, Nargis Abbas, Ahmed Dupont, Jairton Gondal, Humaira Yasmeen |
| author_facet | Mumtaz, Salma Cano, Israel Mumtaz, Nargis Abbas, Ahmed Dupont, Jairton Gondal, Humaira Yasmeen |
| author_sort | Mumtaz, Salma |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T20:27:06Z |
| format | Article |
| id | nottingham-53197 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:27:06Z |
| publishDate | 2018 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-531972020-05-04T19:47:10Z https://eprints.nottingham.ac.uk/53197/ 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 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. Royal Society of Chemistry 2018-08-28 Article PeerReviewed Mumtaz, Salma, Cano, Israel, Mumtaz, Nargis, Abbas, Ahmed, Dupont, Jairton and Gondal, Humaira Yasmeen (2018) Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates. Physical Chemistry Chemical Physics, 20 (32). 20821- 20826. ISSN 1463-9076 Benzimidazolium–based ionic liquids ; Chiral ionic liquids ; Chiral recognition ; Chiral shift agent ; Mosher’s acid https://pubs.rsc.org/en/content/articlelanding/2018/cp/c8cp03881c#!divAbstract doi:10.1039/C8CP03881C doi:10.1039/C8CP03881C |
| spellingShingle | Benzimidazolium–based ionic liquids ; Chiral ionic liquids ; Chiral recognition ; Chiral shift agent ; Mosher’s acid Mumtaz, Salma Cano, Israel Mumtaz, Nargis Abbas, Ahmed Dupont, Jairton Gondal, Humaira Yasmeen Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates |
| title | Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates |
| title_full | Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates |
| title_fullStr | Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates |
| title_full_unstemmed | Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates |
| title_short | Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates |
| title_sort | supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates |
| topic | Benzimidazolium–based ionic liquids ; Chiral ionic liquids ; Chiral recognition ; Chiral shift agent ; Mosher’s acid |
| url | https://eprints.nottingham.ac.uk/53197/ https://eprints.nottingham.ac.uk/53197/ https://eprints.nottingham.ac.uk/53197/ |