Effects of Trifluoroacetic Acid Concentrations in Mobile Phases on HPLC Retention of Zwitterionic and Weakly Basic Triazole Derivatives

References

• LoBrutto , R. , Jones , A. , Kazakevich , Y. V. and McNair , H. M. 2001 . Effect of the eluent pH and acidic modifiers in high‐performance liquid chromatography retention of basic analytes . J. Chromatogr. A , 913 : 173 – 187 .
   PubMed Web of Science ®Google Scholar
• Roberts , J. M. , Diaz , A. R. , Fortin , D. T. , Friedle , J. M. and Piper , S. D. 2002 . Influence of the hofmeister series on the retention of amines in reversed‐phase liquid chromatography . Anal. Chem. , 74 : 4927 – 4932 .
   PubMed Web of Science ®Google Scholar
• Ishikawa , A. and Shibata , T. 1993 . Cellulosic chiral stationary phase under reversed‐phase condition . J. Liq. Chromatogr. , 16 ( 4 ) : 859 – 878 .
   Web of Science ®Google Scholar
• Thompson , R. A. , Ge , Z. , Grinberg , N. , Ellison , D. and Tway , P. 1995 . Mechanistic aspects of the stereospecific interaction for aminoindanol with a crown ether column . Anal. Chem. , 67 : 1580 – 1587 .
   Web of Science ®Google Scholar
• Blackwell , J. A. and Carr , P. W. 1998 . Study of the effect of mobile phase additives on retention in reversed phase HPLC using linear solvation energy relationship . J. High Resol. Chromatogr. , 21 : 427 – 434 .
   Google Scholar
• Vailaya , A. and Horvath , Cs. 1996 . Retention thermodynamics in hydrophobic interaction . Ind. Eng. Chem. Res. , 35 : 2964 – 2981 .
   Web of Science ®Google Scholar
• Horvath , Cs. , Melander , W. and Molnar , I. 1997 . Liquid Chromatography of ionogenic substances with nonpolar stationary phases . Anal. Chem. , 49 : 142 – 154 .
   Google Scholar
• Pilorz , K. and Choma , I. 2004 . Isocratic reversed‐phase high‐performance liquid chromatographic separation of tetracyclines and flumequine controlled by a chaotropic effect . J. Chromatogr. A , 1031 : 303 – 305 .
   PubMed Web of Science ®Google Scholar
• LoBrutto , R. , Jones , A. and Kazakevich , Y. V. 2001 . Effect of counter‐anion concentration on retention in high‐performance liquid chromatography of protonated basic analytes . J. Chromatogr. A , 913 : 189 – 196 .
   PubMed Web of Science ®Google Scholar
• Jones , A. , LoBrutto , R. and Kazakevich , Y. V. 2002 . Effect of counter‐anion type and concentration on the liquid chromatography retention of β‐blockers . J. Chromatogr. A , 964 : 179 – 187 .
   PubMed Web of Science ®Google Scholar
• Pan , L. , LoBrutto , R. , Kazakevich , Y. V. and Thompson , R. 2004 . Influence of inorganic mobile phase additives on the retention, efficiency and peak symmetry of protonated basic compounds in reversed‐phase liquid chromatography . J. Chromatogr. A , 1049 : 63 – 73 .
   PubMed Web of Science ®Google Scholar
• Nagy , P. 1989 . Theoretical calculations on the basicity of amines. Part 2. The influence of hydration . J. Molec. Struc. (Theochem.) , 201 : 271 – 286 .
   Google Scholar
• J. Barbosa , J. , Fonrodona , G. , Marques , I. , Buti , S. and Toro , I. 1997 . Factor analysis applied to the correlation between dissociation constants and solvatochromic parameters in water‐acetonitrile mixture . Trends Anal. Chem. , 16 : 104 – 111 .
   Web of Science ®Google Scholar
• Bacarella , A. L. , Grunwald , E. , Marshall , H. P. and Purlee , E. L. 1955 . The potentiometric measurement of acid dissociation constant and pH in the system methanol‐water. pKa values for carboxylic acids and anilinium ions . J. Org. Chem. , 20 : 747 – 762 .
   Web of Science ®Google Scholar
• McCalley , D. V. 1996 . Effect of organic solvent modifier and nature of solute on the performance of bonded silica reversed‐phase columns for the analysis of strong basic compounds by high‐performance liquid chromatography . J. Chromatogr. A , 738 : 169 – 179 .
   Web of Science ®Google Scholar
• McCalley , D. V. 1997 . Comparative evaluation of bonded‐silica reversed‐phase columns for high‐performance liquid chromatography using strong basic compounds and alternative organic modifiers buffered at acid pH . J. Chromatogr. A , 769 : 169 – 178 .
   Web of Science ®Google Scholar
• Buckenmaier , S. M.C. , McCalley , D. V. and Euerby , M. R. 2003 . Determination of pKa values of organic bases in aqueous acetonitrile solutions using capillary electrophoresis . J. Chromatogr. A , 1004 : 71 – 79 .
   PubMed Web of Science ®Google Scholar
• Buckenmaier , S. M.C. , McCalley , D. V. and Euerby , M. R. 2004 . Determination of ionization constants of organic bases in aqueous methanol solutions using capillary electrophoresis . J. Chromatogr. A , 1026 : 251 – 259 .
   PubMed Web of Science ®Google Scholar
• Sykora , D. , Tesarova , E. and Popl , M. 1997 . Interactions of basic compounds in reversed‐phase high‐performance liquid chromatography. influence of sorbent character, mobile phase composition, and pH on retention of basic compounds . J. Chromatogr. A , 758 : 37 – 51 .
   Web of Science ®Google Scholar
• Espinosa , S. , Bosch , E. and Roses , M. 2000 . Retention of ionizable compounds on HPLC. 5. pH scales and the retention of acids and bases with acetonitrile‐water mobile phases . Anal. Chem. , 72 : 5193 – 5200 .
   PubMed Web of Science ®Google Scholar
• Canals , I. , Valko , K. , Bosch , E. , Hill , A. P. and Roses , M. 2001 . Retention of ionizable compounds on HPLC. 8. Influence of mobile‐phase pH change on the chromatographic retention of acids and bases during gradient elution . Anal. Chem. , 73 : 4937 – 4945 .
   PubMed Web of Science ®Google Scholar
• Espinosa , S. , Bosch , E. and Roses , M. 2002 . Retention of ionizable compounds on HPLC. 12. The properties of liquid chromatography buffers in acetonitrile‐water mobile phases that influence HPLC retention . Anal. Chem. , 74 : 3809 – 3818 .
   PubMed Web of Science ®Google Scholar
• Espinosa , S. , Bosch , E. and Roses , M. 2002 . Retention of ionizable compounds on high‐performance liquid chromatography. IX. Modelling retention in reversed‐phase liquid chromatography as a function of pH and solvent composition with acetonitrile‐water mobile phases . J. Chromatogr. A , 947 : 47 – 58 .
   PubMed Web of Science ®Google Scholar
• Espinosa , S. , Bosch , E. and Roses , M. 2002 . Retention of ionizable compounds on high‐performance liquid chromatography. 14. Acid‐base pK values in acetonitrile‐water mobile phases . J. Chromatogr. A , 964 : 55 – 66 .
   PubMed Web of Science ®Google Scholar
• Heinisch , S. W. and Rocca , J. L. 2004 . Effect of mobile phase composition, pH and buffer type on the retention of ionizable compounds in reversed‐phase liquid chromatography: application to method development . J. Chromatogr. A , 1048 : 183 – 193 .
   PubMed Web of Science ®Google Scholar
• Barbosa , J. and Sanz‐Nebot , V. 1994 . Preferential solvation in acetonitrile‐water mixtures . J. Chem. Soc., Faraday Trans. , 90 : 3287 – 3292 .
   Google Scholar
• Barbosa , J. , Beltran , J. L. and Sanz‐Nebot , V. 1994 . Ionization constants of pH reference materials in acetonitrile‐water mixture up to 70% (w/w) . Anal. Chem. Acta , 288 : 271 – 278 .
   Web of Science ®Google Scholar
• Bosch , E. , Bou , P. , Allemann , H. and Roses , M. 1996 . Retention of ionizable compounds on HPLC. pH scale in methanol‐water and the pK and pH values of buffers . Anal. Chem. , 68 : 3651 – 3657 .
   Web of Science ®Google Scholar
• Roses , M. , Canals , I. , Allemann , H. , Siigur , K. and Bosch , E. 1996 . Retention of ionizable compounds on HPLC. 2. Effect of pH, ionic strength, and mobile phase composition on the retention of weak acids . Anal. Chem. , 68 : 4094 – 4100 .
   PubMed Web of Science ®Google Scholar
• Barbosa , J. and Sanz‐Nebot , V. 1995 . Assignment of reference pH‐values to primary standard buffer solutions for standardization of potentiometric sensors in acetonitrile‐water mixtures . Fresenius J. Anal. Chem. , 353 : 148 – 155 .
   Google Scholar
• Bosch , E. , Espinosa , S. and Roses , M. 1998 . Retention of ionizable compounds on high‐performance liquid chromatography. III. Variation of pK values of acids and pH values of buffers in acetonitrile‐water mobile phases . J. Chromatogr. A , 824 : 137 – 146 .
   Web of Science ®Google Scholar
• Subrirats , X. , Bosch , E. and Roses , M. 2004 . Retention of ionizable compounds on high‐performance liquid chromatography. XV. Estimation of pH variation of aqueous buffers with the change of the acetonitrile fraction of the mobile phase . J. Chromatogr. A , 1059 : 33 – 42 .
   PubMed Web of Science ®Google Scholar
• Lawson , E. C. , Maryanoff , B. E. and Hoekstra , W. J. 2001 . Synthesis of triazolopyridines as conformationally constrained tertiary amides . Tetrahedron Lett. , 41 : 4533 – 4536 .
   Web of Science ®Google Scholar
• Hoekstra , W. J. , Lawson , E. C. and Maryanoff , B. E. “ Preparation of triazolopyridines as GPIIb/IIIa antagonists ” . PCT Int. Appl. (2000) WO2000006570
   Google Scholar
• Bonanomi , M. and Biaocchi , L. 1983 . Reaction between ethyl ω‐chloroalkylimidates and hydrazides . J. Heterocycl. Chem. , 20 : 1657 – 1660 .
   Web of Science ®Google Scholar