title: New chiral zwitterionic phosphorus heterocycles: synthesis, structure, properties and application as chiral solvating agents.
abstract: A family of new chiral zwitterionic phosphorus-containing heterocycles (zPHC) have been derived from methylene-bridged bis(imidazolines). These structures were unambiguously determined, including single-crystal XRD analysis for two compounds. The stability, acid/base and electronic properties of these dipolar phosphorus heterocycles were subsequently investigated. zPHCs can be successfully employed as a new class of chiral solvating agents for the enantiodifferentiation of chiral carboxylic and sulfonic acids by NMR spectroscopy. The stoichiometry and binding constants for the donor-acceptor complexes formed were established by NMR titration methods.
authors.affiliation: Department of Chemistry, Imperial College London, Exhibition Road, SW7 2AZ London, UK.
authors.forename: Andrey E
authors.initials: AE
authors.lastname: Sheshenev
authors.forename: Ekaterina V
authors.initials: EV
authors.lastname: Boltukhina
authors.forename: Anastasiya A
authors.initials: AA
authors.lastname: Grishina
authors.forename: Ivana
authors.initials: I
authors.lastname: Cisařova
authors.forename: Ilya M
authors.initials: IM
authors.lastname: Lyapkalo
authors.forename: King Kuok Mimi
authors.initials: KK
authors.lastname: Hii
mesh_terms: D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D010758:Phosphorus / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D012997:Solvents; D010758:Phosphorus