Computational and experimental study of the structure preferences binding preferences, and spectroscopy of nickel(II) and petroleum vanadyl porphyrins in petroleum

Journal of Physical Chemistry B

Volumn 114, Issue 6, 2010, Pages 2180-2188

  Stoyanov, Stanislav R ^a   Yin, Cindy Xing ^b   Gray, Murray R ^b   Stryker, Jeffrey M ^b   Gusarov, Sergey ^a   Kovalenko, Andrly ^a,b  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; COMPLEXATION; CONTINUUM MECHANICS; COORDINATION REACTIONS; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; EXCITED STATES; HEAVY OIL PRODUCTION; HYDROGEN BONDS; METAL RECOVERY; NICKEL COMPOUNDS; NUCLEAR ENERGY; ORGANIC SOLVENTS; PORPHYRINS; POTENTIAL ENERGY; PROBABILITY DENSITY FUNCTION; SINGLE CRYSTALS; VANADIUM COMPOUNDS;

AROMATIC FRAGMENTS; AXIAL COORDINATION; BAND ENERGY; BASIS SETS; BATHOCHROMIC SHIFT; CHLOROFORM SOLVENTS; COMPUTATIONAL EXPLORATION; DENSITY FUNCTIONALS; ELECTROSTATIC POTENTIALS; EXCITED-STATE ENERGY; EXPERIMENTAL STUDIES; FUKUI FUNCTIONS; FUNCTIONALS; HEAVY OIL; HEAVY OIL UPGRADING; HETEROCYCLES; HYDROGEN BONDINGS; LINEAR CORRECTIONS; METALLOPORPHYRINS; POLARIZABLE CONTINUUM MODEL; REMOVAL METHOD; SORET BANDS; SPECTROSCOPIC BEHAVIOR; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; VANADYL; VISIBLE ABSORPTION SPECTROSCOPY;

ABSORPTION SPECTROSCOPY;

EID: 77449127270     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp908641t     Document Type: Article

References (105)

1. Yen, T. F. Role Trace Met. Pet. 1975, 7, 30.
2. Filby, R. H. Role Trace Met. Pet. 1975, 31. 58.
3. Treibs, A. Liebigs. Ann. 1934, 509, 103 Ibid. 510, 42.
4. (a) Callot, H. J.; Ocampo, R. In The Porphyrin Handbook; Kadish, K. M, Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000; Vol.1, p 349;
5. (b) Czernuszewicz, R. S. J. Porphyrim Phthalocyanines 2000, 4, 426.
6. (c) Kashiyama, Y.; Shiro, M.; Tada, R.; Ohkouchi, N. Chem. Lett. 2007, 36, 706.
7. Smith, K. M. Porph. Metalloporph. 1975, 3, 28.
8. Sugihara, J. M.; Bean, R. M. J. Chem. Eng. Data 1962, 7, 269271.
9. Dickie, J. P.; Yen, T. F. Anal. Chem. 1967, 39, 1847-1852
10. Yin, C.-X.; Tan, X.; Mullen, K.; Stryker, J. M.; Gray, M. Enerev Fuels 2008, 22, 2465-2469.
11. Qian, K.; Mennito, A. S.; Edwards, K. E.; Ferrughelli, D. T. Rapid Cmmun. Mass Spectrom. 2008, 22, 21, 53-2160.
12. Caughey, W. S.; Deal, R. M.; McLees, B. D.; Alben, J. O. J. Am. Chem. Soc. 1962, 84, 1735. (11)
13. (a) Kim, D. H.; Kirmaier, C.; Holten, D. Chem. Phys. 1983, 75, 305.
14. (b) Findsen, E. W.; Shellnut, J. A.; Freidman, J. M.; Ondaris, M. R. Chem. Phys. Lett. 1983, 98, 584.
15. Rodriguez, J.; Holten, D. J. Chem. Phys. 1990, 92, 5944-5950.
16. Senge, M. O. J. Porphyrins Phthalocyanines 1998, 2, 107.
17. Ghosh, S. K.; Patra, R.; Rath, S. P. Inore. Chem. 2008, 47, 9848.
18. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
19. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2005, 709, 5656.
20. Schultz, N. E.; Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2005, 709, 11127-11143.
21. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2005, 7, 415432.
22. (a) Tsuzuki, S.; Lutlii, H. P. J, Chem, Phys 2001, 114, 3949.
23. (b) Johnson, E. R.; Wolkow, R. A.; DiLabio, G. A. Chem. Phys. Lett. 2004, 394, 334-338.
24. Strassner, T.; Taige, M. A. J. Chem Theory Comout. 2005, 7, 848855.
25. Inada, Y.; Orita, H. J. Comput. Chem 2007, 29, 225.
26. Delley, B. J. Phys, Chem, A 2006, 110, 13632-13639.
27. Li, Q.; Gusarav, S; Evoy, S.; Kovalenko, A. J, Phys, Chem, C 2009, 113, 9958-9967.
28. (a) Monat, J. E.; Rodriguez, J. H.; McCusker, J. K. J. Phys, Chem, A 2002, 106, 7399.
29. (b) Rodrigues, J. H.; Wheeler, D. E.; McCusker, J. K. J. Am. Chem. Soc. 1998, 720, 12051.
30. (c) Stoyanov, S. R.; Villegas, J. M.; Riliema, D. P. Inorg, Chem. 2003, 42, 7852.
31. (d) Stoyanov, S. R.; Villegas, J. M.; Cruz, A. J.; Lockyear, L. L.; Reibenspies, J. H.; Riliema, D. P. J. Chem. Theory Comout. 2005, 1, 95-106.
32. Stoyanov, S. R.; Villegas, J. M.; Riliema, D. P. Inorg. Chem. Commun. 2004, 7, 838.
33. Kozlowski, P. M.; Kuta, J.; Ohia, T.; Kitagawa, T. J. Inorg. Biochem. 2006, 100, 744.
34. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys, 1998, 708, 4439.
35. Roy, R. K.; Krishnamurti, S.; Geerlings, P.; PaI, S. J. Phys. Chem. A 1998, 102, 3746.
36. Deka, R. Ch.; Roy, R. K.; Hirao, K. Chem. Phys. Lett. 2004, 389, 186.
37. Cardenas-Jiron, G. L; Venegas-Yazigi, D. A. J. Phys, Chem, A 2002, 106, 11938.
38. Cardenas-Jiron, G. I.; Caro, C. A.; Venegas-Yazigi, D.; Zagal, J. H. J. Mol. Struct. Theochem 2002, 580, 193.
39. Cardenas-Jiron, G. I. Int. J. Quantum Chem. 2003, 97, 389-397.
40. Stoyanov, S. R.; Gusarav, S.; Kuznicki, S. M.; Kovalenko, A. J. Phys. Chem. C 2008. 112. 6794-6810.
41. Stoyanov, S. R.; Gusarav, S.; Kovalenko, A. Mol. Simul. 2008, 34, 943-951.
42. (a) Stewart, J. J. P. J. Mol. Model. 2007, 13,1173.
43. (b) Pople, J. A.; Sauny, D. P. J. Chem. Phys. 1965, 43, S129.
44. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
45. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
46. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
47. Perdew, J. P. In Electronic Structure of Solids 91;
48. Ziesche, P., Esching, H., FxIs.; Akademie Verlag: Berlin, Germany, 1991; p 11.
49. Lee, C.; Yang, W.; Pan-, R. G. Phys, Rev, B 1988, 37, 785-789.
50. Gill, P. M. W. Mol. Phys. 1996, 89, 433.
51. (a) Xu, X.; Goddard III, W. A. Proc. Natl. Acad. Sci. 2004, 101, 2673.
52. (b) Xu, X.; Zhang, Q.; Muller, R. P.; Goddard III, W. A. J. Chem. Phys. 2005, 122, 014105.
53. (a) Handy, N. C.; Cohen, A. J. Mol. Phys. 2001, 9.9,403
54. . (b) Wilson, P. J.; Bradley, T. J.; Tozer, D. J. J. Chem. Phys. 2001, 115, 9233.
55. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.
56. (a) Becke, A. D. J. Chem, Phys. 1996, 104, 1040.
57. (b) Zhao, Y.; Gonzalez-Garcia, N.; Truhlar, D. G. J. Phys. Chem. A 2005, 109, 2012.
58. (a) Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
59. (b) Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. 1997, 78, 1396E.
60. (a) Adamo, C.; Cossi, M.; Barone, V. THEOCHEM 1999, 493, 145.
61. (b) Ernzerhof, M.; Scuseria, G. E. J. Chem. Phys. 1999, 110, 5029.
62. (a) Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1992, 46, 66716687.
63. (b) Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys, Rev. B 1993, 48, 4978.
64. (a) Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B 1996, 54, 16533.
65. (b) Burke, K.; Perdew, J. P.; Wang, Y. In Electronic Density Functional Theory: Recent Progress and New Directions; Dobson, J. F., ; Vignale, G., ; Das, M. P., Eds.; Plenum: New York, 1998.
66. Tao, J.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Phys. Rev. Lett. 2003, 97, 146401.
67. (a) Roothaan, C. C. J, Rev, Mod, Phys. 1951. 23, 69.
68. (b) Pople, J. A.; Nesbet, R. K. J. Chem. Phys. 1954, 22, 571-572
69. (c) McWeeny, R.; Dierksen, G. J. Chem. Phys. 1968, 49, 4852.
70. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, L; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomel'ii, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Parkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Chal'lacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
71. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
72. (a) McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
73. (b) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
74. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218.
75. Bauernschmitt, R.; Ahlrichs, R. Chem, Phys. Lett. 1996, 256, 454.
76. Cossi, M.; Barone, V. J. Chem. Phys. 2001, 115, 4708.
77. (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998. 102, 1995.
78. (b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.
79. Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 5631-5637.
80. Bonnett, R.; Brewer, P.; Noro, K.; Noro, T. Tetraheran 1978, 34, 379-385.
81. Vosko, S. J.; WiIk, L.; Nusair, M. Can. J. Phys. 1980, 58, 12001211.
82. Hamprecht, F. A.; Cohem, A. J.; Tozer, D. J.; Handy, N. C. J. Chem. Phys. 1998, 109, 6264.
83. Hammer, B.; Hansen, L. B.; Norskov, J. K. Phys. Rev. B 1999, 59, 7413.
84. Delley B. J. Chem Phys. 1990, 92, 508.
85. 3, release 4.0; Accelrys, Inc., CA, 2001.
86. Delley, B. J. ChEm. Phys. 1990, 92, 508.
87. Weinert, M.; Davenport, J. W. Phys. Rev. B 1992, 45, 13709.
88. For example: Kruglik, S. G.; Ermolenkov, V. V.; Orlovich, V. A.; Turpin, P.-Y. Chem. Phys. 2003, 286, 97-108.
89. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533-3539.
90. Hemelsoet, K.; Lesthaeghe, D.; Van Speybroek, V.; Waroquier, M. Chem Phys, Lett. 2006, 419, 10-15.
91. Klopman, G. The general perturbation theory of chemical reactivity and its applications. In Chemical reactivity and reaction paths; Klopman, G., Ed.; Wlley-Interscience: New York, 1974; pp 55-165.
92. Fukui, K.; Yonezawa, T.; Nagata, C. Bull. Chem. Soc Jpn. 1954, 27, 423-427.
93. Fukui, K. Science 1987, 218, 747-754.
94. Parr, R. G.; Yang, W. J. Am. Chem. Soc. 1984, 106, 4049.
95. Kirner, J. F.; Garofalo, J., Jr.; Scheidt, W. R. Inorg. Nucl. Chem. Lett. 1975, 11, 107.
96. Sun, M.; Nelson, A. E.; Adjaye, J. J. Mol. 2004, 222, 243-251.
97. Pettersen, R. C. Acta Crvstalloer. B 1969, 25, 2527.
98. Lavoie, S.; Mahieu, G.; McBreen, P. H. Angew. Chem. Int. Ed, 2006, 45, 7404-7407.
99. Bencosme, C. S.; Romero, C.; Simoni, S. Inorg. Chem. 1985, 24, 1603-1604.
100. Higginbotham, E.; Hambright, P. Inorg. Nucl. Chem. Lett. 1972, 8, 747-750.
101. Su, Y. O.; Czernuszewicz, R. S.; Miller, L. A.; Spiro, T. G. J. Am. Chem. Soc. 1988, 110, 4150-4157.
102. For example: Dulak, M.; Bergougnant, R.; Fromm, K. M.; Hagemann, H. R.; Robin, A. Y.; Wesolowski, T. Spectrochim. Acta A 2006, 64, 532.
103. Kovalenko, A. Three-dimensional RISM theory for molecular liquids and solid-liquid interfaces. In Understanding Chemical Reactivity: Molecular Theory ofSolvatimi, Hirata, F., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003; Vol.24, pp 169-275.
104. In the current literature, asphaltene structures are categorized as belonging to the continental or the archipelago models. The continental (or pericondensed) model is based on a core aromatic group containing a large number of fused rings (usually more than seven rings) with pendant aliphatic groups. The archipelago model suggests that asphaltenes consist of smaller aromatic groups (composed of 2-4 aromatic heterocyclic rings) linked by aliphatic bridges (
105. Sheremata, J. M.; Gray, M. R.; Dettman, H. D.; McCaffrey, W. C. Energy Fuels 2004, 18, 1377 and references therein).