Competition between intra- and intermolecular hydrogen bonding: Effect on para/ortho adsorptive selectivity for substituted phenols

Industrial and Engineering Chemistry Research

Volumn 39, Issue 2, 2000, Pages 463-472

  Glemza, Amy Jo ^a   Mardis, Kristy L ^b   Chaudhry, Asiya A ^a   Gilson, Michael K ^b   Payne, Gregory F ^a,c  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

^b NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

^c UNIVERSITY OF MARYLAND BIOTECHNOLOGY INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; COMPLEXATION; ESTERS; FREE ENERGY; INFRARED SPECTROSCOPY; ISOMERS; NUMERICAL METHODS; OXYGEN; PHASE EQUILIBRIA; PHENOLS; SOLVENTS; SUBSTITUTION REACTIONS;

ADSORPTIVE SELECTIVITY; CARBONYL OXYGEN; INTRAMOLECULAR HYDROGEN BONDING INTERACTIONS; ISOMER BINDING AFFINITIES; P-HYDROXYACETOPHENONE; P-METHYL HYDROXYBENZOATE; SMALL MOLECULE ETHYL PROPIONATE;

HYDROGEN BONDS;

PHENOL DERIVATIVE;

ADSORPTION; ANALYTIC METHOD; ARTICLE; COMPLEX FORMATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; RECEPTOR AFFINITY;

EID: 0034144449     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie990594i     Document Type: Article

References (42)

1. Tamada, J. A.; King, C. J. Extraction of Carboxylic Acids with Amine Extractants. 2. Chemical Interactions and Interpretation of Data. Ind. Eng. Chem. Res. 1990, 29, 1327.
2. Wolbach, J. P.; Sandler, S. I. Thermodynamics of Hydrogen Bonding from Molecular Orbital Theory: 1. Water. AIChE J. 1997, 43, 1589.
3. Wolbach, J. P.; Sandler, S. I. Thermodynamics of Hydrogen Bonding from Molecular Orbital Theory: 1. Organics. AIChE J. 1997, 43, 1597.
4. Wolbach, J. P.; Sandler, S. I. Using Molecular Orbital Calculations to Describe the Phase Behavior of Hydrogen-Bonding Fluids. Ind. Eng. Chem. Res. 1997, 36, 4041.
5. Wolbach, J. P.; Sandler, S. I. Using Molecular Orbital Calculations to Describe the Phase Behavior of Cross-associating Mixtures. Ind. Eng. Chem. Res. 1998, 37, 2917.
6. Sum, A. K.; Sandler, S. I. A Novel Approach to Phase Equilibria Predictions Using Ab Initio Methods. Ind. Eng Chem Res. 1999, 38, 2849.
7. Brinkley, R. L.; Gupta, R. B. Intra-and Intermolecular Hydrogen Bonding of 2-Methoxyethanol and 2-Butoxyethanol in n-Hexane. Ind. Eng. Chem. Res. 1998, 37, 4823.
8. 2-Miscible Anthraquinones. Ind. Eng. Chem. Res. 1999, 38, 2824.
9. Stoeckli, F.; Huguenin, D. Water Adsorption in Active Carbon Characterized by Adsorption and Immersion Techniques. J. Chem. Soc., Faraday Trans. 1992, 88, 737.
10. Muller, E. A.; Rull, L. F.; Vega, L. F.; Gubbins, K. E. Adsorption of Water on Activated Carbons: Molecular Simulation Study. J. Phys. Chem. 1996, 100, 1189.
11. Natal-Santiago, M. A.; Hill, J. M.; Dumesic, J. A. Studies of the Adsorption of Acetaldehyde, Methyl Acetate, Ethyl Acetate, and Methyl Trifluoroacetate on Silica. J. Mol. Catal. A. Chem 1999, 140, 199.
12. Kempe, M.; Mosbach, K. Molecular Imprinting Used for Chiral Separations. J. Chromatogr, A. 1995, 694, 3.
13. Bell, T. W.; Hou, Z.; Luo, Y.; Drew, M. G. B.; Chapoteau, E.; Czech, B. P.; Kumar, A. Detection of Creatinine by a Designed Receptor. Science 1995. 269, 671.
14. Cram, D. J. Preorganization - From Solvents to Spherands. Angew. Chem., Int. Ed. Engl. 1986, 25, 1039.
15. Lehn, J. Supramolecular Chemistry - Scope and Perspectives Molecules, Supermolecules, and Molecular Devices. Angew. Chem., Int. Ed. Engl. 1988, 27, 89.
16. Maity, N.; Payne, G. F.; Chipchosky, J. L. Adsorptive Separations Based on the Differences in Solute-Sorbent Hydrogen Bonding Strengths. Ind. Eng. Chem. Res. 1991, 30, 2456.
17. Brune, B. J.; Payne, G. F.; Chaubal, M. V. Linear Solvation Energy Relationships to Explain Interactions Responsible for Solute Adsorption onto a Polar Polymeric Sorbent. Langmuir 1997, 13, 5766.
18. +-Exchanged Resins and Cuprous Halides. Langmuir 1995, 11, 3450.
19. Chen, N.; Yang, R. T. Ab Initio Molecular Orbital Study of Adsorption of Oxygen, Nitrogen, and Ethylene on Silver-Zeolite and Silver Halides. Ind. Eng. Chem. Res. 1996, 35, 4020.
20. +. Ind. Eng. Chem. Res. 1999, 38, 2720.
21. Shelley, J. C.; Berard, D. R. Computer Simulation of Water Physisorption at Metal-Water Interfaces. Rev. Comput. Chem. 1998, 12, 137.
22. Brune, B. J.; Koehler, J. A.; Smith, P. J.; Payne, G. F. Correlation between Adsorption and Small Molecule Hydrogen Bonding. Langmuir 1999, 15, 3987.
23. Glemza, A. J.; Koehler, J. A.; Bune, B. J.; Payne, G. F. Selective Adsorption of Methoxyphenol Positional Isomers. Ind. Eng. Chem. Res. 1998, 37, 3685.
24. Mardis, K. L.; Glemza, A. J.; Brune, B. J.; Payne, G. F.; Gilson, M. K. The Differential Adsorption of Phenol Derivatives onto a Polymeric Sorbent: A Combined Molecular Modeling and Experimental Study. J. Phys. Chem. B 1999, 103, 9879.
25. Berthelot, M.; Laurence, C.; Foucher, D.; Taft, R. W. Partition Coefficients and Intramolecular Hydrogen Bonding. 1. The Hydrogen-Bond Basicity of Intramolecular Hydrogen-Bond Heteroatoms. J. Phys. Org. Chem. 1996, 9, 255.
26. Berthelot, M.; Laurence, C.; Lucon, M.; Rossignol, C.; Taft, R. W. Partition Coefficients and Intramolecular Hydrogen Bonding. 2. The Influence of Partition Solvents on the Intramolecular Hydrogen-Bond Stability of Salicylic Acid Derivatives. J. Phys. Org. Chem. 1996, 9, 626.
27. Hill, T. L. Cooperativity Theory in Biochemistry; Springer Verlag: New York, 1985; p 8 ff.
28. Gilson, M. K.; Given, J. A.; Bush B. L.; McCammon, J. A. The Statistical-Thermodynamic Basis for Computation of Binding Affinities: A Critical Review. Biophys. J. 1997, 72, 1047.
29. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J. CHARMm: A Program for Macromolecular Energy, Minimization and Dynamics Calculations. J. Comput. Chem. 1983, 4, 187.
30. Schlenkrich, M.; Brickmann, J.; A. D. MacKerrell, J.; Karplus, M. In Biological Membranes: A Molecular Perspective from Computation and Experiment; Merz, K. M., Roux, B., Eds.; Birkhauser: Boston, 1996; p 31.
31. Hawkins, G. D.; Cramer, C. J.; Truhlar, D. G. Universal Quantum Mechanical Model for Solvation Free Energies Based on Gas-Phase Geometries. J. Phys. Chem. B 1998, 102, 3257.
32. Luo, R.; Head, M. S.; Given, J. A.; Gilson, M. K. Nucleic Acid Base-Pairing and n-Methylacetamide Self-Association in Chloroform: Affinity and Conformation. Biophys. Chem. 1999, 78, 183.
33. Gilson, M. K.; Sharp, K. A.; Honig, B. H. Calculating the Electrostatic Potential of Molecules in Solution - Method and Error Assessment. J. Comput. Chem. 1988, 9, 327.
34. Gilson, M. K.; Honig, B. H. Calculation of the Total Electrostatic Energy of a Macromolecular System: Solvation Energies, Binding Energies and Conformational Analysis. Proteins: Struct. Func. Gen. 1988, 4, 7.
35. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semianalytical Treatment of Solvation for Molecular Mechanics and Dynamics. J. Am. Chem. Soc. 1990. 112, 6127.
36. Qiu, D.; Shenkin, P. S.; Hollinger, F. P.; Still, W. C. The GB/SA Continuum Model for Solvation. A Fast Analytical Method for the Calculation of Approximate Born Radii. J. Phys. Chem. 1997, 101, 3005.
37. Gilson, M. K.; Honig, B. The Inclusion of Electrostatic Hydration Energies in Molecular Mechanics Calculations. J. Comput Aid Mol. Des. 1991, 5, 5.
38. Head, M. S.; Given, J. A.; Gilson, M. K. "Mining Minima": Direct Computation of Conformational Free Energy. J. Phys. Chem. A 1997, 101, 1609.
39. Davis, M. E.; Madura, J. D.; Luty, B. A.; McCammon, J. A. Electrostatics and Diffusion of Molecules in Solution - Simulations with the University of Houston-Brownian Dynamics Program. Comput. Phys. Commun. 1991, 62, 187.
40. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. General Atomic and Molecular Electronic-Structure System. J. Comput. Chem. 1993, 14, 1347.
41. Cuma, M.; Scheiner, S.; Kar, T. Competition between Rotamerization and Proton Transfer in o-Hydroxybenzaldehyde. J. Am. Chem. Soc. 1998, 120, 10497.
42. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford: New York, 1997.