Cyclodextrin-modified micellar electrokinetic capillary chromatography separations of benzopyrene isomers. Correlation with computationally derived host-guest energies

Journal Article · Fri Dec 31 23:00:00 EST 1993 · Analytical Chemistry (Washington); (United States)

DOI:https://doi.org/10.1021/ac00073a025· OSTI ID:7114503

Copper, C L; Sepaniak, M J ^[1]

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1. Univ. of Tennessee, Knoxville, TN (United States)

General adjustment of system retention is often inadequate to resolve structurally similar compounds in micellar electrokinetic capillary chromatography (MECC). The use of cyclodextrins (CDs) as mobile-phase additives is described for separations of structural isomers. CDs are shown to provide dramatic and selective effects on the retention of benzopyrene isomers. Efficient separations of six methyl-substituted and three 1-position-substituted benzopyrene isomers are presented. Derivatized [gamma]-CD discriminates between substitutional isomers less than native [gamma]-CD. A comparison of sodium dodecylsulfate (SDS) and sodium cholate (NaC) surfactant systems indicates that SDS-CD mobile phases are more favorable for separation of benzopyrene isomers. Possible separation mechanisms are discussed and evaluated based on results of these studies. The computational procedures of a commercial molecular modeling system are modified and used to determine interaction energies for various host-guest (i.e., [gamma]-CD-benzopyrene) combinations. By use of the average of the five best energy values from interaction energy matrices, correct elution order is predicted for the 1-position-substituted and most of the methyl-substituted benzopyrene isomers. Consideration of different possible CD-benzopyrene orientations must be made to correctly predict elution order. Inspection of the interaction energy matrices revealed no obvious energy barriers that would inhibit inclusion complex formation. 28 refs., 4 figs., 2 tabs.

• OSTI ID: 7114503
• Journal Information: Analytical Chemistry (Washington); (United States), Journal Name: Analytical Chemistry (Washington); (United States) Vol. 66:1; ISSN 0003-2700; ISSN ANCHAM
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400100* -- Analytical & Separations Chemistry
400201 -- Chemical & Physicochemical Properties
AROMATICS
BENZOPYRENE
CAPILLARY FLOW
CARBOHYDRATES
CHEMICAL REACTIONS
CHROMATOGRAPHY
COMPILED DATA
COMPLEXES
CONDENSED AROMATICS
DATA
DERIVATIZATION
DEXTRIN
ELECTRODYNAMICS
FLUID FLOW
HYDROCARBONS
INFORMATION
ISOMERIZATION
ISOMERS
LIQUID COLUMN CHROMATOGRAPHY
MATHEMATICAL MODELS
MICELLAR SYSTEMS
MOLECULAR MODELS
NUMERICAL DATA
ORGANIC COMPOUNDS
POLYSACCHARIDES
SACCHARIDES
SEPARATION PROCESSES
SURFACTANTS