Microcolumn liquid chromatography of polycyclic aromatic hydrocarbons and some isomeric compounds on cyclodextrin stationary phases

Preparative-grade bonded β- and γ-cyclodextrin stationary phases were used as the packing material of liquid chromato-graphic analytical microcolumns. Although the resulting columns are characterized by relatively low efficiency, the high selectivity of the cyclodextrin phases nevertheless allows their successful use for the separation of different classes of isomeric compounds that are difficult to resolve on conventional LC stationary phases. Examples of baseline (or almost baseline) separations of a number of isomeric compounds, including isomeric polycyclic aromatic hydrocarbons, are presented to demonstrate the analytical potential of such columns. Retention behavior of the separated isomers is discussed based on the structure of the solute molecule and the possibility of its inclusion into the molecular cavity of cyclodextrin stationary phases.

[1]  J. Haginaka,et al.  Beta-cyclodextrin bonded silica for direct injection analysis of drug enantiomers in serum by liquid chromatography. , 1990, Analytical chemistry.

[2]  D. Armstrong,et al.  Polar-liquid, derivatized cyclodextrin stationary phases for the capillary gas chromatography separation of enantiomers. , 1990, Analytical chemistry.

[3]  R. Rosset,et al.  Chiral Resolutions in SFC: Mechanisms and Applications with Various Chiral Stationary Phases , 1989 .

[4]  T. Oe,et al.  Chromatographic Behavior of Bile Acids Using Cyclodextrin in Mobile Phase of High Performance Liquid Chromatography , 1989 .

[5]  Y. Nikitin,et al.  The effect of the structure of bonded cyanoalkyl stationary phases on their selectivity in the liquid chromatographic separation of polynuclear aromatic hydrocarbons , 1989 .

[6]  T. Shono,et al.  Liquid chromatographic separation of racemates on acetylated or carbamoylated β-cyclodextrin-bonded stationary phases , 1989 .

[7]  T. Shono,et al.  2, 6-Di-O-methylated Cyclodextrin-Bonded Stationary Phases for Liquid Chromatography , 1989 .

[8]  H. Matsui,et al.  High-performance liquid chromatographic separation of urinary hippuric and o-, m- and p-methylhippuric acids with a beta-cyclodextrin-bonded column. , 1989, Journal of Chromatography A.

[9]  F. Marziani,et al.  Liquid chromatographic separation of positional isomers of suprofen on a cyclodextrin-bonded phase. , 1989, Journal of chromatography.

[10]  M. Petersheim,et al.  Structural basis for enantiomeric resolution of pseudoephedrine and the failure to resolve ephedrine by using beta-cyclodextrin mobile phases. , 1988, Analytical chemistry.

[11]  S. Ransom,et al.  Inclusion complex formation of benzo[a]pyrene metabolites with cyclodextrins. , 1988, Analytical chemistry.

[12]  L. Feltl,et al.  Micropacked columns with a β‐cyclodextrin stationary phase , 1988 .

[13]  H. Issaq The Multimodal Cyclodextrin Bonded Stationary Phases for High Performance Liquid Chromatography , 1988 .

[14]  H. Aboul‐Enein,et al.  Direct HPLC resolution of racemic nomifensine hydrogen maleate using a chiral beta-cyclodextrin-bonded stationary phase , 1988 .

[15]  G. Alexander,et al.  Cyclodextrins and their derivatives as stationary phases in GC capillary columns , 1988 .

[16]  G. Patonay,et al.  The Influence of Mobile Phase Alcohol Modifiers on HPLC of Polycyclic Aromatics Using Bonded Phase Cyclodextrin Columns , 1988 .

[17]  E. Smolková-Keulemansová,et al.  β-cyclodextrin as a selective agent for separation of selected aromatic acids by high-performance liquid chromatography , 1988 .

[18]  J. Blais,et al.  Improvement in the fluorimetric detection of 5-methoxypsoralen by using β-cyclodextrin in the mobile phase and a cross-linked β-cyclodextrin column , 1988 .

[19]  A. Krstulović,et al.  Enantiomeric analysis of a new anti-inflammatory agent in rat plasma using a chiral beta-cyclodextrin stationary phase. , 1988, Journal of chromatography.

[20]  R. A. Zeeuw,et al.  COMPARISON OF 2 BETA-CYCLODEXTRIN BONDED STATIONARY PHASES FOR HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY - ELUTION ORDER AND OPTICAL PURITY OF ENANTIOMERS OF CYCLOHEXYLPHENYLGLYCOLIC ACID , 1987 .

[21]  J. Maguire Some structural requirements for resolution of hydantoin enantiomers with a beta-cyclodextrin liquid chromatography column. , 1987, Journal of chromatography.

[22]  N. Pattabiraman,et al.  Separation of tamoxifen geometric isomers and metabolites by bonded-phase beta-cyclodextrin chromatography. , 1987, Journal of Chromatography A.

[23]  J. Jurczak,et al.  Application of a gas-liquid chromatography system with α-cyclodextrin for monitoring the stereochemical course of β-pinene hydrogenation , 1986 .

[24]  J. Bojarşki,et al.  Resolution of Mephenytoin and Some Chiral Barbiturates into Enantiomers by Reversed Phase High Performance Liquid Chromatography via β-Cyclodextrin Inclusion Complexes , 1986 .

[25]  T. Ando,et al.  Optical Resolution of Some Mandelic Derivatives on a Chemically Bonded Cyclodextrin Stationary Phase , 1986 .

[26]  K. Hattori,et al.  Charged cyclodextrins as stationaly phases in high-performance liquid chromatography. , 1986 .

[27]  B. Snider Separation of cis-trans isomers of prostaglandins with a cyclodextrin bonded column , 1986 .

[28]  D. Armstrong,et al.  Efficient detection and evaluation of cyclodextrin multiple complex formation , 1986 .

[29]  T. Shono,et al.  Methylated cyclodextrin-bonded stationary phases for liquid chromatography , 1986 .

[30]  G. Szepesi,et al.  α-, β- and γ-cyclodextrins as mobile phase additives in the high-performance liquid chromatographic separation of enantiomeric compounds , 1986 .

[31]  L. Tan,et al.  Normal-phase high-performance liquid chromatographic separations of positional isomers of substituted benzoic acids with amine and beta-cyclodextrin bonded-phase columns. , 1986, Journal of chromatography.

[32]  D. Sybilska,et al.  α- and β-cyclodextrins as selective agents for the separation of isomers by reversed-phase high-performance thin-layer and column liquid chromatography , 1985 .

[33]  J. Jurczak,et al.  Resolution of ortho, meta, and para isomers of some disubstituted benzene derivatives via .alpha.- and .beta.-cyclodextrin inclusion complexes, using reversed-phase high-performance liquid chromatography , 1985 .

[34]  D. Armstrong,et al.  Separation of mycotoxins, polycyclic aromatic hydrocarbons, quinones, and heterocyclic compounds on cyclodextrin bonded phases: An alternative lc packing , 1985 .

[35]  D. Armstrong,et al.  Separation of metallocene enantiomers by liquid chromatography: chiral recognition via cyclodextrin bonded phases , 1985 .

[36]  D. Armstrong,et al.  Liquid Chromatographic Separation of Diastereomers and Structural Isomers on Cyclodextrin-Bonded Phases , 1985 .

[37]  J. Mann,et al.  The synthesis of lignans and related structures using quinodimethanes and isobenzofurans: approaches to the podophyllins , 1984 .

[38]  D. Armstrong,et al.  Cyclodextrin Bonded Phases For the Liquid Chromatographic Separation of Optical, Geometrical, and Structural Isomers , 1984 .

[39]  D. Armstrong,et al.  Facile separation of enantiomers, geometrical isomers, and routine compounds on stable cyclodextrin LC bonded phases , 1984 .

[40]  J. Jurczak,et al.  α-and β-cyclodextrin complexation as a tool for the separation of o-, m- and p-nitro-cis and trans-cinnamic acids by reversed-phase high-performance liquid chromatography , 1984 .

[41]  K. Jinno,et al.  Computer-assisted retention prediction system for reversed-phase micro high-performance liquid chromatography , 1984 .

[42]  E. Smolková-Keulemansová Cyclodextrins as stationary phases in chromatography , 1982 .

[43]  T. Shono,et al.  Retention Behaviour of Benzene Derivatives on Chemically Bonded β-Cyclodextrin Phases , 1981 .

[44]  W. Hinze Applications of Cyclodextrins in Chromatographic Separations and Purification Methods , 1981 .

[45]  Wolfram Saenger,et al.  Cyclodextrin Inclusion Compounds in Research and Industry , 1980 .

[46]  D. Armstrong Pseudophase Liquid Chromatography: Applications to TLC , 1980 .

[47]  Y. Matsui,et al.  Binding forces contributing to the association of cyclodextrin with alcohol in an aqueous solution. , 1979 .

[48]  R. Bergeron,et al.  Disposition requirements for binding in aqueous solution of polar substrates in the cyclohexaamylose cavity , 1977 .

[49]  R. Rohrbach,et al.  Small anion binding to cycloamylose. Equilibrium constants , 1975 .

[50]  N. Atherton,et al.  Association of di-t-butyl nitroxide with Schardinger dextrins , 1975 .

[51]  L. Hansen,et al.  Thermodynamics of binding of guest molecules to α- and β-cyclodextrins , 1973 .

[52]  D. Griffiths,et al.  Cycloamyloses as Catalysts , 1973 .

[53]  W. Saenger,et al.  Inclusion Compounds. XIX.1a The Formation of Inclusion Compounds of α-Cyclodextrin in Aqueous Solutions. Thermodynamics and Kinetics , 1967 .

[54]  H. Schlenk,et al.  The Association of α- and β-Cyclodextrins with Organic Acids1 , 1961 .