Liquid Chromatography Enantioseparations of Halogenated Compounds on Polysaccharide‐Based Chiral Stationary Phases: Role of Halogen Substituents in Molecular Recognition. Issue 10 (3rd August 2015)

• Record Type: Journal Article
• Authors: Peluso, Paola; Mamane, Victor; Cossu, Sergio
• Is Part Of: Chirality. Volume 27:Issue 10(2015)
• Page Start: 667
• Page End: 684
• Publication Date: 2015-08-03
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22485
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p>Halogenated chiral molecules have become important in several fields of science, industry, and society as drugs, natural compounds, agrochemicals, environmental pollutants, synthetic products, and chiral supports. Meanwhile, the perception of the halogen moiety in organic compounds and its role in recognition processes changed. Indeed, the recognition of the halogen bond as an <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">intermolecular</named-content> interaction occurring when the halogen acts as a Lewis acid had a strong impact, particularly in <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">crystal engineering</named-content> and medicinal chemistry. Due to this renewed interest in the potentialities of chiral organohalogens, here we focus on selected recent applications dealing with enantioseparations of halogenated compounds on polysaccharide‐based chiral stationary phases (CSPs), widely used in <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">liquid chromatography</named-content> (LC). In particular, recently the first case of halogen bonding‐driven high‐performance LC (HPLC) enantioseparation was reported on a cellulose‐based CSP. Along with enantioseparations performed under conventional HPLC, representative applications using <named-content content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">supercritical fluid chromatography</named-content> (SFC) are reported. <italic>Chirality 27:667–684, 2015</italic>. © 2015 Wiley Periodicals, Inc.</p> </abstract>