Effect of lattice topology on the adsorption of benzyl alcohol on kaolinite surfaces: Quantum chemical calculations of geometry optimization, binding energy, and NMR chemical shielding

American Mineralogist

Volumn 94, Issue 10, 2009, Pages 1392-1404

  Lee, Bum Han ^a   Lee, Sung Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

Benzyl alcohol; Kaolinite; Lattice topology; NMR chemical shielding; Quantum chemical calculations; Surface adsorption

Indexed keywords

ADSORPTION; COMPUTATION THEORY; ELECTRIC NETWORK TOPOLOGY; HYDROGEN BONDS; KAOLINITE; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM CHEMISTRY; SHIELDING; SILICATES; TOPOLOGY; UNCERTAINTY ANALYSIS;

BENZYL ALCOHOL; CHEMICAL SHIELDING; LATTICE TOPOLOGY; QUANTUM CHEMICAL CALCULATIONS; SURFACE ADSORPTION;

BINDING ENERGY;

ADSORPTION; ALCOHOL; CHEMICAL ANALYSIS; HYDROGEN; ISOTOPIC ANALYSIS; KAOLINITE; LATTICE DYNAMICS; NUCLEAR MAGNETIC RESONANCE; OPTIMIZATION; QUANTUM MECHANICS;

EID: 75649089800     PISSN: 0003004X     EISSN: None     Source Type: Journal    
DOI: 10.2138/am.2009.3198     Document Type: Article

References (104)

1. Adiga, S., Aebi, D., and Bryce, D.L. (2007) EFGShield-A program for parsing and summarizing the results of electric field gradient and nuclear magnetic shielding tensor calculations. Canadian Journal of Chemistry, 85, 496-505.
2. Anderson, W.G. (1986) Wettability literature survey-Part 1: Rock-oil-brine interactions and the effects of core handling on wettability. Journal of Petroleum Technology, 38, 1125-1144.
3. Aquino, A.J.A., Tunega, D., Haberhauer, G., Gerzabek, M.H., and Lischka, H. (2007) Quantum chemical adsorption studies on the (110) surface of the mineral goethite. Journal of Physical Chemistry C, 111, 877-885.
4. Bantignies, J.L., Moulin, C.C.D., and Dexpert, H. (1998) Asphaltene adsorption on kaolinite characterized by infrared and X-ray absorption spectroscopies. Journal of Petroleum Science and Engineering, 20, 233-237.
5. Becke, A.D. (1993a) Density-functional thermochemistry. III. The role of exact exchange. Journal of Chemical Physics, 98, 5648-5652.
6. - (1993b) A new mixing of Hartree-Fock and local density-functional theories. Journal of Chemical Physics, 98, 1372-1377.
7. Bish, D.L. (1993) Rietveld refinement of the kaolinite structure at 1.5 K. Clays and Clay Minerals, 41, 738-744.
8. Bish, D.L. and von Dreele, R.B. (1989) Rietveld refinement of non-hydrogen atomic positions in kaolinite. Clays and Clay Minerals, 37, 289-296.
9. Boulet, P., Greenwell, H.C., Stackhouse, S., and Coveney, P.V. (2006) Recent advances in understanding the structure and reactivity of clays using electronic structure calculations. Journal of Molecular Structure: THEOCHEM, 762, 33-48.
10. Boys, S.F. and Bernardi, F. (1970) The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Molecular Physics, 19, 553-566.
11. Brown, G.E.J., Calas, G., Waychunas, G.A., and Petiau, J. (1988) X-ray absorption-spectroscopy and its applications in mineralogy and geochemistry. In F.C. Hawthorne, Ed., Spectroscopic Methods in Mineralogy and Geology, 18, p. 431-512. Reviews in Mineralogy, Mineralogical Society of America, Chantilly, Virginia.
12. Brown Jr., G.E., Henrich, V.E., Casey, W.H., Clark, D.L., Eggleston, C., Felmy, A., Goodman, D.W., Grätzel, M., Maciel, G., McCarthy, M.I., Nealson, K.H., Sverjensky, D.A., Toney, M.F., and Zachara, J.M. (1999) Metal oxide surfaces and their interactions with aqueous solutions and microbial organisms. Chemical Reviews, 99, 77-174.
13. Castro, E.A.S. and Martins, J.B.L. (2005) Theoretical study of benzene interaction on kaolinite. Journal of Computer-Aided Materials Design, 12, 121-129.
14. Chu, P.-J., Potrzebowski, M.J., Gao, Y., and Scott, A.I. (1990) Conformational studies of N-benzoyl-L-phenylalanine by combined rotation and multiple-pulse spectroscopy 1H nuclear magnetic resonance. Journal of the American Chemical Society, 112, 881-883.
15. Cremer, D. (1998) Møller-Plesset Perturbation Theory. In P. von Rague-Schleyer, Ed., Encyclopedia of Computational Chemistry, 3, p. 1706-1735. Wiley, New York.
16. Crespo-Otero, R., Montero, L.A., Stohrer, W.-D., and de la Vega, J.M.G. (2005) Basis set superposition error in MP2 and density-functional theory: A case of methane-nitric oxide association. Journal of Chemical Physics, 123, 134107.
17. Cygan, R.T. and Kubicki, J.D. (2001) Molecular modeling theory: Applications in the geosciences. In R.T. Cygan and J.D. Kubicki, Eds., Molecular Modeling Theory: Applications in the Geosciences, 42, p. 531. Reviews in Mineralogy and Geochemistry, Mineralogical Society of America, Chantilly, Virginia.
18. Feng, X.J., Simpson, A.J., and Simpson, M.J. (2005) Chemical and mineralogical controls on humic acid sorption to clay mineral surfaces. Organic Geochemistry, 36, 1553-1566.
19. Førland, G.M. (2001) Adsorption of benzyl alcohol onto alumina and kaolinite surfaces from a nonaqueous solution. Journal of Colloid and Interface Science, 242, 477-479.
20. Førland, G.M., Borve, K.J., Hoiland, H., and Skauge, A. (1995) Adsorption of short-chain alcohols from decane solutions onto kaolinite. Journal of Colloid and Interface Science, 171, 261-269.
21. Foresman, J.B. and Frisch, Æ. (1996) Exploring Chemistry with Electronic Structure Methods, 302 p. Gaussian, Inc., Pittsburgh, Pennsylvania.
22. Frisch, M.J., and others (2004) Gaussian 03. Gaussian, Inc., Wallingford, Connecticut.
23. Gorb, L., Lutchyn, R., Zub, Y., Leszczynska, D., and Leszczynski, J. (2006) The origin of the interaction of 1,3,5-trinitrobenzene with siloxane surface of clay minerals. Journal of Molecular Structure: THEOCHEM, 766, 151-157.
24. Granqvist, B., Sandberg, T., and Hotokka, M. (2007) Adsorption of organic probes on silica through Lewis interactions: A comparison of experimental results and quantum chemical calculations. Journal of Colloid and Interface Science, 310, 369-376.
25. Haase, F. and Sauer, J. (1994) 1H NMR chemical-shifts of ammonia, methanol, and water molecules interacting with Brønsted acid sites of zeolite catalysts: ab-initio calculations. Journal of Physical Chemistry, 98, 3083-3085.
26. - (1995) Interaction of methanol with Brønsted acid sites of zeolite catalysts: an ab initio study. Journal of the American Chemical Society, 117, 3780-3789.
27. Hobbs, J.D., Cygan, R.T., Nagy, K.L., Schultz, P.A., and Sears, M.P. (1997) All-atom ab initio energy minimization of the kaolinite crystal structure. American Mineralogist, 82, 657-662.
28. 2]- on kaolinite surfaces: Quantum chemistry calculations. Canadian Mineralogist, 39, 1591-1596.
29. Hong, H.L., Min, X.M., and Fu, Z.Y. (2002) Study on adsorption of submicrometer gold on kaolinite by quantum chemistry calculations. American Mineralogist, 87, 1-4.
30. Huang, M.J., Lee, K.S., and Hurley, S.J. (2005) Nuclear magnetic resonance spectral analysis and molecular properties of berberine. International Journal of Quantum Chemistry, 105, 396-409.
31. Johansson, U., Holmgren, A., Forsling, W., and Frost, R.L. (1999) Adsorption of silane coupling agents onto kaolinite surfaces. Clay Minerals, 34, 239-246.
32. C NMR studies of the interaction of aceton, carbon tetrachloride and trichloroethylene with soil components. The Science of the Total Environment, 164, 195-202.
33. Kelleher, B.P. and O'Dwyer, T.F. (2002) Intercalation of benzamide into expanded kaolinite under ambient environmental conditions. Clays and Clay Minerals, 50, 331-335.
34. Knezovich, J.P., Harrison, F.L., and Wilhelm, R.G. (1987) The bioavailability of sediment-sorbed organic chemicals: A review. Water, Air, snd Soil Pollution, 32, 233-245.
35. Kowalska, M., Guler, H., and Cocke, D.L. (1994) Interactions of clay minerals with organic pollutants. The Science of the Total Environment, 141, 223-240.
36. Krossner, M. and Sauer, J. (1996) Interaction of water with Brønsted acidic sites of zeolite catalysts. Ab initio study of 1:1 and 2:1 surface complexes. Journal of Physical Chemistry, 100, 6199-6211.
37. Kubicki, J.D., Schroeter, L.M., Itoh, M.J., Nguyen, B.N., and Apitz, S.E. (1999) Attenuated total reflectance Fourier-transform infrared spectroscopy of carboxylic acids adsorbed onto mineral surfaces. Geochimica et Cosmochimica Acta, 63, 2709-2725.
38. Kwon, K.D., Vadillo-Rodriguez, V., Logan, B.E., and Kubicki, J.D. (2006) Interactions of biopolymers with silica surfaces: Force measurements and electronic structure calculation studies. Geochimica et Cosmochimica Acta, 70, 3803-3819.
39. Lee, C., Yang, W., and Parr, R.G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785-789.
40. Lee, S.K. (2004) Structure of silicate glasses and melts at high pressure: Quantum chemical calculations and solid-state NMR. Journal of Physical Chemistry B, 108, 5889-5900.
41. 17O NMR and quantum chemical calculations. Journal of Physical Chemistry B, 110, 16408-16412.
42. 17O MAS and 3QMAS NMR study. American Mineralogist, 88, 493-500.
43. - (2006) Disorder and the extent of polymerization in calcium silicate and aluminosilicate glasses: O-17 NMR results and quantum chemical molecular orbital calculations. Geochimica et Cosmochimica Acta, 70, 4275-4286.
44. 17O solid-state NMR study. American Mineralogist, 93, 1066-1071.
45. 17O and 11B NMR. Journal of Physical Chemistry B, 105, 12583-12595.
46. 17O and 27Al MAS and 3QMAS NMR study of synthetic and natural layer-silicates. Chemistry of Materials, 15, 2605-2613.
47. Lee, S.Y. and Kim, S.J. (2002) Adsorption of naphtalene by HDTMA modified kaolinite and halloysite. Applied Clay Science, 22, 55-63.
48. Li, Y.C. and Gupta, G. (1994) Adsorption of hydrocarbons by clay-minerals from gasoline. Journal of Hazourdous Materials, 38, 105-112.
49. Madsen, L., Grahl-Madsen, L., Gron, C., Lind, I., and Engell, J. (1996) Adsorption of polar aromatic hydrocarbons on synthetic calcite. Organic Geochemistry, 24, 1151-1155.
50. Mehring, M. (1983) Principles of High Resolution NMR in Solids, 342 p. Springer-Verlag, Berlin.
51. Michalkova, A., Tunega, D., and Nagy, L.T. (2002) Theoretical study of interactions of dickite and kaolinite with small organic molecules. Journal of Molecular Structure: THEOCHEM, 581, 37-49.
52. Michalkova, A., Gorb, L., Ilchenko, M., Zhikol, O.A., Shishkin, O.V., and Leszczynski, J. (2004) Adsorption of sarin and soman on dickite: An ab initio ONIOM study. Journal of Physical Chemistry B, 108, 1918-1930.
53. Michalkova, A., Szymczak, I.J., and Leszczynski, J. (2005) Adsorption of 2,4-dinitrotoluene on dickite: The role of H-bonding. Structural Chemistry, 16, 325-337.
54. Molina, J.M., Dobado, J.A., Daza, M.C., and Villaveces, J.L. (2002) Structure and bonding of weak hydrogen peroxide complexes. Journal of Molecular Structure: THEOCHEM, 580, 117-126.
55. Møller, C. and Plesset, M.S. (1934) Note on an approximation treatment for many-electron systems. Physical Review, 46, 618-622.
56. Murgich, J., Rodriguez M., J., Izquierdo, A., Carbognani, L., and Rogel, E. (1998) Interatomic interactions in the adsorption of asphaltenes and resins on kaolinite calculated by molecular dynamics. Energy & Fuels, 12, 339-343.
57. 13C CP/MAS and 31P NMR study of the interactions of dipalmitoylphosphatidylcholine with respirable silica and kaolin. Journal of Colloid and Interface Science, 288, 166-170.
58. Ogawa, M. and Kuroda, K. (1995) Photofunctions of intercalation compounds. Chemical Reviews, 95, 399-438.
59. Olejnik, S., Posner, A.M., and Quirk, J.P. (1970) The interaction of polar organic compounds into kaolinite. Clay Minerals, 8, 421-434.
60. Ottonello, G. and Zuccolini, M.V. (2005) Ab-initio structure, energy and stable Cr isotopes equilibrium fractionation of some geochemically relevant H-O-Cr-Cl complexes. Geochimica et Cosmochimica Acta, 69, 851-874.
61. Pérez-Jordá, J.M. and Becke, A.D. (1995) A density-functional study of van der Waals forces: rare gas diatomics. Chemical Physics Letters, 233, 134-137.
62. Parthasarathi, R. and Subramanian, V. (2006) Characterization of hydrogen bonding: From van der Waals interactions to covalency In S.J. Grabowski, Ed. Hydrogen Bonding - New Insights, 3, p. 1-50. Springer, Dordrecht.
63. Pelmenschikov, A. and Leszczynski, J. (1999) Adsorption of 1,3,5-trinitrobenzene on the siloxane sites of clay minerals: Ab initio calculations of molecular models. Journal of Physical Chemistry B, 103, 6886-6890.
64. Pelmenschikov, A., Strandh, H., Pettersson, L.G.M., and Leszczynski, J. (2000) Lattice resistance to hydrolysis of Si-O-Si bonds of silicate minerals: Ab initio calculations of a single water attack onto the (001) and (111) β-cristobalite surfaces. Journal of Physical Chemistry B, 104, 5779-5783.
65. Pelmenschikov, A.G., Morosi, G., and Gamba, A. (1992) Quantum chemical molecular models of oxides. 2. Methanol adsorption on silica and zeolites. Journal of Physical Chemistry, 96, 2241-2246.
66. Pinnavaia, T.J. and Beall, G.W. (2000) Polymer-Clay Nanocomposites, p. 349. Wiley, New York.
67. Plant, D.F., Simperler, A., and Bell, R.G. (2006) Adsorption of methanol on zeolites X and Y. An atomistic and quantum chemical study. Journal of Physical Chemistry B, 110, 6170-6178.
68. Robinson, T.L., Michalkova, A., Gorb, L., and Leszczynski, J. (2007) Hydrogen bonding of thymine and uracil with surface of dickite: An ab initio study. Journal of Molecular Structure: THEOCHEM, 844-845, 48-58.
69. Rozas, I. (2007) On the nature of hydrogen bonds: An overview on computational studies and a word about patterns. Physical Chemistry Chemical Physics, 9, 2782-2790.
70. Sauer, J., Ugliengo, P., Garrone, E., and Saunders, V.R. (1994) Theoretical study of van der Waals complexes at surface sites in comparison with the experiment. Chemical Reviews, 94, 2095-2160.
71. Schauble, E.A., Rossman, G.R., and Taylor, J.H.P. (2001) Theoretical estimates of equilibrium Fe-isotope fractionation from vibrational spectroscopy. Geochimica et Cosmochimica Acta, 65, 2487-2497.
72. - (2003) Theoretical estimates of equilibrium chlorine-isotope fractionation. Geochimica et Cosmochimica Acta, 67, 3267-3281.
73. - (2004) Theoretical estimates of equilibrium chromium-isotope fractionation. Chemical Geology, 205, 99-114.
74. Seger, M.R. and Maciel, G.E. (2006) NMR investigation of the behavior of an organothiophosphate pesticide, chlorpyrifos, sorbed on soil components. Environmental Science and Technology, 40, 791-796.
75. 3 compared to benzene using the exaltation of magnetic susceptibility criterion and a comparison of calculated and experimental NMR chemical shifts in these compounds. Journal of the American Chemical Society, 118, 7345-7352.
76. 13C NMR parameters. Journal of Physical Chemistry B, 106, 10944-10954.
77. 13C NMR shift parameters. Journal of Physical Chemistry B, 108, 7142-7151.
78. Solans-Monfort, X., Sodupe, M., Mó, O., Yáñez, M., and Elguero, J. (2005) Hydrogen bond vs proton transfer in HZSM5 zeolite. A theoretical study. Journal of Physical Chemistry B, 109, 19301-19308.
79. Stebbins, J.F. (1995) Nuclear magnetic resonance spectroscopy of silicates and oxides in geochemistry and geophysics. In T.J. Ahrens, Ed., Handbook of Physical Constants, 2, p. 303-332. American Geophysical Union, Washington, D.C.
80. Stone, A.J. (1996) The Theory of Intermolecular Forces, 264 p. Clarendon Press, Oxford.
81. Suh, J.H., Lee, S.K., and Lee, I. (2007) Quantum chemical calculations of equilibrium copper (I) isotope fractionations in ore-forming fluids. ChemicalGeology, 243, 225-237.
82. 2 oxidative addition. Journal of Physical Chemistry, 100, 19357-19363.
83. 13C NMR study of co-contamination of clays with carbon tetrachloride and benzene. Environmental Science and Technology, 32, 350-357.
84. Teppen, B.J., Yu, C.H., Miller, D.M., and Schafer, L. (1998) Molecular dynamics simulations of sorption of organic compounds at the clay mineral/aqueous solution interface. Jounal of Computational Chemistry, 19, 144-153.
85. Thomas, J.E. and Kelley, M.J. (2008) Interaction of mineral surfaces with simple organic molecules by diffuse reflectance IR spectroscopy (DRIFT). Journal of Colloid and Interface Science, 322, 516-526.
86. Tossell, J.A. (2001) Calculating the NMR properties of minerals, glasses, and aqueous species. In R.T. Cygan and J.D. Kubicki, Eds., Molecular Modeling Theory: Applications in the Geosciences, 42, p. 437-458. Reviews in Mineralogy and Geochemistry, Mineralogical Society of America, Chantilly, Virginia.
87. - (2005) Calculating the partitioning of the isotopes of Mo between oxidic and sulfidic species in aqueous solution. Geochimica et Cosmochimica Acta, 69, 2981-2993.
88. Tunega, D., Benco, L., Haberhauer, G., Gerzabek, M.H., and Lischka, H. (2002a) Ab initio molecular dynamics study of adsorption sites on the (001) surfaces of 1:1 dioctahedral clay minerals. Journal of Physical Chemistry B, 106, 11515-11525.
89. Tunega, D., Haberhauer, G., Gerzabek, M.H., and Lischka, H. (2002b) Theoretical study of adsorption sites on the (001) surfaces of 1:1 clay minerals. Langmuir, 18, 139-147.
90. - (2004) Sorption of phenoxyacetic acid herbicides on the kaolinite mineral surface-an ab initio molecular dynamics simulation. Soil Science, 169, 44-54.
91. Tunney, J.J. and Detellier, C. (1996) Aluminosilicate nanocomposite materials. Poly(ethylene glycol)-kaolinite intercalates. Chemistry of Materials, 8, 927-935.
92. van Duin, A.C.T. and Larter, S.R. (2001) Molecular dynamics investigation into the adsorption of organic compounds on kaolinite surfaces. Organic Geochemistry, 32, 143-150.
93. Viruela-Martín, P., Zicovich-Wilson, C.M., and Corma, A. (1993) Ab initio molecular orbital calculations of the protonation reaction of propylene and isobutene by acidic OH groups of isomorpbously substituted zeolites. Journal of Physical Chemistry, 97, 13713-13719.
94. Wang, K.J. and Xing, B.S. (2005) Structural and sorption characteristics of adsorbed humic acid on clay minerals. Journal of Environmental Quality, 34, 342-349.
95. Wasylishen, R.E. and Bryce, D.L. (2002) A revised experimental absolute magnetic shelding scale for oxygen. Journal of Chemical Physics, 117, 10061-10066.
96. Wiberg, K.B., Hammer, J.D., Zilm, K.W., and Cheeseman, J.R. (1999) NMR chemical shifts. 3. A comparison of acetylene, allene, and the higher cumulenes. Journal of Organic Chemistry, 64, 6394-6400.
97. Winkler, P., Novoszad, M., Gerzabek, M.H., Haberhauer, G., Tunega, D., and Lischka, H. (2007) Interaction of naphthalene derivatives with soil: An experimental and theoretical case study. European Journal of Soil Science, 58, 967-977. (Pubitemid 47084137)
98. Xie, X. and Hayashi, S. (1999) NMR study of kaolinite intercalation compounds with formamide and its derivatives. 1. Structure and orientation of guest molecules. Journal of Physical Chemistry B, 103, 5949-5955.
99. 17O and 1H NMR properties and local structures in silicates: An ab initio calculation. Physics and Chemistry of Minerals, 26, 14-30.
100. Yariv, S. (1996) Thermo-IR-spectroscopy analysis of the interactions between organic pollutants and clay minerals. Thermochimica Acta, 274, 1-35.
101. Yariv, S. and Lapides, I. (2000) The effect of mechanochemical treatments on clay minerals and the mechanochemical adsorption of organic materials onto clay minerals. Journal of Materials Synthesis and Processing, 8, 223-233.
102. 1H MAS NMR at high spinning speeds. Journal of the American Chemical Society, 109, 6274-6282.
103. Yoon, T.H., Johnson, S.B., Musgrave, C.B., and Brown, G.E. (2004) Adsorption of organic matter at mineral/water interfaces: I. ATR-FTIR spectroscopic and quantum chemical study of oxalate adsorbed at boehmite/water and corundum/water interfaces. Geochimica et Cosmochimica Acta, 68, 4505-4518.
104. Zhanpeisov, N.U., Adams, J.W., Larson, S.L., Weiss, C.A., Zhanpeisova, B.Z., Leszczynska, D., and Leszczynski, J. (1999) Cluster quantum chemical study of triaminotoluene interaction with a model clay surface. Structural Chemistry, 10, 285-294.