title: Chiral separations and quantitative analysis of optical isomers on cellulose tribenzoate plates.
abstract: In this paper new cellulose tribenzoate/gypsum layers in the ratio up to 8/1 (w/w) were investigated for the chiral resolution of closely related aromatic ketones (e.g. tetralones and indanones), alcohols (e.g. benzhydrols) and racemates or enantiomers of other compound classes (e.g. dinitrophenyl amino acids). Among 22 investigated compounds, 16 racemates were baseline or partially resolved by eluting with methanol or 2-propanol/water mixtures on 4/1 (w/w) layers. The best results were compared with those achieved on microcrystalline cellulose triacetate plates and on cellulose tribenzoate columns. The study of structurally related solutes allowed us to increase the knowledge of the retention and resolution mechanisms on this chiral stationary phase and to highlight the role of π-π interactions between cellulose tribenzoate and solutes with different substituents on the aromatic ring. However, some results were unexpected and confirmed the complexity of enantioseparation mechanisms, thus evidencing the importance of experimental tests. Densitometric scan in the visible region of cellulose tribenzoate/gypsum plates after their exposure to iodine vapours allowed us to successfully perform the quantitative analysis of the investigated compounds, thus overcoming the detection problems normally encountered with this stationary phase.
authors.affiliation: Department of Chemistry, University of Florence, Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy. delbubba@unifi.it
authors.forename: M
authors.initials: M
authors.lastname: Del Bubba
authors.forename: A
authors.initials: A
authors.lastname: Cincinelli
authors.forename: L
authors.initials: L
authors.lastname: Checchini
authors.forename: L
authors.initials: L
authors.lastname: Lepri
mesh_terms: D000596:Amino Acids / Q000302:isolation & purification; D001565:Benzoates / Q000737:chemistry*; D002133:Calcium Sulfate / Q000737:chemistry; D002482:Cellulose / Q000031:analogs & derivatives / Q000737:chemistry*; D002855:Chromatography, Thin Layer / Q000295:instrumentation / Q000379:methods*; D004136:Dinitrobenzenes / Q000302:isolation & purification; D006841:Hydrocarbons, Aromatic / Q000302:isolation & purification; D016018:Least-Squares Analysis; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001565:Benzoates; D004136:Dinitrobenzenes; D006841:Hydrocarbons, Aromatic; D002482:Cellulose; C024671:cellulose triacetate; D002133:Calcium Sulfate