A theoretical investigation on conformers of imidazolinium salts
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A theoretical investigation on conformers of imidazolinium salts Abdelkader Ladjarafi1,2 · Hacène Meghezzi2 · Jean‑François Halet3 Received: 17 June 2020 / Accepted: 5 October 2020 © Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Structures, energies, and electronic properties of anti- and syn-atropisomeric conformers of some chiral imidazolinium salts bearing a substituted aromatic ring have been computed and compared at the B3LYP/6-311+G(d,p) level of density functional theory. Results indicate that the presence of a bulky substituent on the ortho position of the aromatic ring present in these compounds is mainly responsible of the chiral discrimination due to high interconversional energy barriers. Keywords Atropisomerism · Density functional theory · Electronic properties · Imidazolinium salts
1 Introduction Over the last years, there has been an increasing interest in ionic liquids (ILs) commonly known as green solvents [1–14]. Indeed, the number of publications concerning ionic liquids reaches 3500 articles per year, and up to now more than 75,000 publications and 12,000 patents in total were published [14–16]. One of the main reasons is that the development of new clean processes to minimize chemical waste has become very important and in that context, ILs such as imidazolium, imidazolinium and pyridinium salts can be used as clean solvents in organic chemistry with a wide variety of remarkable physicochemical properties and enormous potential applications: chemical synthesis and catalysis [17–26], separation processes [27–32], optical devices [33–40], batteries [41–44], lubrication [45–48], Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00214-020-02677-x) contains supplementary material, which is available to authorized users. * Abdelkader Ladjarafi [email protected] * Jean‑François Halet halet@univ‑rennes1.fr 1
Department of Chemistry, Faculty of Exact Sciences and Computer Sciences, University Ziane Achour, UZAD, Djelfa, Algeria
2
Laboratory of Thermodynamics and Molecular Modelling, Faculty of Chemistry, USTHB, Algiers, Algeria
3
Institut des Sciences Chimiques de Rennes (ISCR), UMR 6226, Univ Rennes, CNRS, 35000 Rennes, France
biological and other applications such as in pharmacy and medicine [49–60] to mention a few. Research has also shown that some of these imidazolium salts reveal interesting biological properties, particularly with regard to antitumor and antimicrobial activities and could be potentially useful as antifungal, antibiotics or inhibitory agents against pathogenic mushrooms [61–71]. A thorough literature analysis on ILs suggests also that bio-medical applications of ILs should become one of the major research trends in this domain [72–74]. In this context, a series of chiral imidazolinium salts and derivatives have been synthesized and characterized by different groups [75–94], especially the group of Mauduit in Rennes, aiming at investigating their potential in chiral molecul
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