title: Solvation of phenylglycine- and leucine-derived chiral stationary phases: molecular dynamics simulation study.
abstract: A theoretical study of the solvation of ( R)- N-(3,5-dinitrobenzoyl)phenylglycine- and ( R)- N-(3,5-dinitrobenzoyl)leucine-derived chiral stationary phases (CSPs) is presented. Semiflexible models of the chiral selectors are prepared from B3LYP/6-311G** calculations, and these are used in the molecular dynamics simulations of the corresponding interface. The chiral interface is examined for four solvents: 100% hexane, 90:10 hexane:2-propanol, 80:20 hexane:2-propanol, and 100% 2-propanol. Despite the similarities between phenylglycine and leucine, the interfaces are distinct both in terms of the selector orientations at the surface and in the number of hydrogen bonds formed with 2-propanol. We also find that an increase in alcohol concentration alters the preferred orientations of the selectors.
authors.affiliation: Department of Chemistry, Queen's University, Kingston, Ontario, Canada.
authors.forename: Sorin
authors.initials: S
authors.lastname: Nita
authors.forename: Natalie M
authors.initials: NM
authors.lastname: Cann
mesh_terms: D000465:Algorithms; D055598:Chemical Phenomena; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D006860:Hydrogen Bonding; D007930:Leucine / Q000031:analogs & derivatives* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009579:Nitrobenzoates / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D009579:Nitrobenzoates; D012997:Solvents; C051871:N-(3,5-dinitrobenzoyl)phenylglycine; C051872:N-(3,5-dinitrobenzoyl)leucine; D007930:Leucine; D005998:Glycine