title: Enantioselective complexation of chiral propylene oxide by an enantiopure water-soluble cryptophane.
abstract: ECD and NMR experiments show that the complexation of propylene oxide (PrO) within the cavity of an enantiopure water-soluble cryptophane 1 in NaOH solution is enantioselective and that the (R)-PrO@PP-1 diastereomer is more stable than the (S)-PrO@PP-1 diastereomer with a free energy difference of 1.7 kJ/mol. This result has been confirmed by molecular dynamics (MD) and ab initio calculations. The enantioselectivity is preserved in LiOH and KOH solutions even though the binding constants decrease, whereas PrO is not complexed in CsOH solution.
authors.affiliation: Institut des Sciences Moléculaires (UMR 5255-CNRS), Université Bordeaux 1, 351 Cours de la Libération, 33405 Talence, France.
authors.forename: Aude
authors.initials: A
authors.lastname: Bouchet
authors.forename: Thierry
authors.initials: T
authors.lastname: Brotin
authors.forename: Mathieu
authors.initials: M
authors.lastname: Linares
authors.forename: Hans
authors.initials: H
authors.lastname: Ågren
authors.forename: Dominique
authors.initials: D
authors.lastname: Cavagnat
authors.forename: Thierry
authors.initials: T
authors.lastname: Buffeteau
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000737:chemistry*; D012995:Solubility; D013237:Stereoisomerism; D013379:Substrate Specificity; D013816:Thermodynamics; D014867:Water / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D011083:Polycyclic Compounds; C523242:cryptophane; D014867:Water; C009068:propylene oxide