Cation-π Interactions: Accurate intermolecular potential from symmetry-adapted perturbation theory

Journal of Physical Chemistry B

Volumn 117, Issue 35, 2013, Pages 10093-10102

  Ansorg, Kay ^a   Tafipolsky, Maxim ^a   Engels, Bernd ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE MOLECULES; CHARGE PENETRATION; ELECTROSTATIC ENERGIES; ENERGY COMPONENTS; INTERMOLECULAR INTERACTION ENERGIES; INTERMOLECULAR POTENTIALS; POLARIZABLE POTENTIAL; SYMMETRY ADAPTED PERTURBATION THEORY;

BENZENE; DISPERSIONS; ELECTROSTATICS;

POSITIVE IONS;

EID: 84883668509     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp403578r     Document Type: Article

References (93)

1. Stone, A. J. The Theory of Intermolecular Forces; Oxford University Press: Oxford, 2013.
2. Jeziorski, B.; Moszynski, R.; Szalewicz, K. Perturbation-Theory Approach to Intermolecular Potential-Energy Surfaces of Van-der-Waals Complexes Chem. Rev. 1994, 94, 1887-1930
3. Heßelmann, A.; Jansen, G. The Helium Dimer Potential from a Combined Density Functional Theory and Symmetry-Adapted Perturbation Theory Approach Using an Exact Exchange-Correlation Potential Phys. Chem. Chem. Phys. 2003, 5, 5010-5014
4. Heßelmann, A.; Jansen, G.; Schutz, M. Density-Functional Theory-Symmetry-Adapted Intermolecular Perturbation Theory with Density Fitting: A New Efficient Method to Study Intermolecular Interaction Energies J. Chem. Phys. 2005, 122, 014103
5. Bukowski, R.; Podeszwa, R.; Szalewicz, K. Efficient Calculation of Coupled Kohn-Sham Dynamic Susceptibility Functions and Dispersion Energies with Density Fitting Chem. Phys. Lett. 2005, 414, 111-116
6. Podeszwa, R.; Bukowski, R.; Szalewicz, K. Density-Fitting Method in Symmetry-Adapted Perturbation Theory Based on Kohn-Sham Description of Monomers J. Chem. Theory Comput. 2006, 2, 400-412
7. Hohenstein, E. G.; Sherrill, C. D. Density Fitting of Intramonomer Correlation Effects in Symmetry-Adapted Perturbation Theory J. Chem. Phys. 2010, 133, 014101
8. Tekin, A.; Jansen, G. How Accurate Is the Density Functional Theory Combined With Symmetry-Adapted Perturbation Theory Approach for CH-π and π-π Interactions? A Comparison To Supermolecular Calculations for the Acetylene-Benzene Dimer Phys. Chem. Chem. Phys. 2007, 9, 1680-1687
9. Misquitta, A. J.; Szalewicz, K. Symmetry-Adapted Perturbation-Theory Calculations of Intermolecular Forces Employing Density-Functional Description of Monomers J. Chem. Phys. 2005, 122, 214109
10. Mooij, W. T. M.; van Duijneveldt, F. B.; van Duijneveldt-van de Rijdt, J. G. C. M.; van Eijck, B. P. Transferable Ab Initio Intermolecular Potentials. 1. Derivation from Methanol Dimer and Trimer Calculations J. Phys. Chem. A 1999, 103, 9872-9882
11. Špirko, V.; Engvist, O.; Soldán, P.; Selzle, H. L.; Schlag, E. W.; Hobza, P. Structure and Vibrational Dynamics of the Benzene Dimer J. Chem. Phys. 1999, 111, 572-582
12. Mitchell, J. B. O.; Price, S. L. A Systematic Nonempirical Method of Deriving Model Intermolecular Potentials for Organic Molecules: Application To Amides J. Phys. Chem. A 2000, 104, 10958-10971
13. Hloucha, M.; Sum, A. K.; Sandler, S. I. Computer simulation of acetonitrile and methanol with ab initio-based pair potentials J. Chem. Phys. 2000, 113, 5401-5406
14. Engkvist, O.; Åstrand, P. O.; Karlström, G. Accurate Intermolecular Potentials Obtained from Molecular Wave Functions: Bridging the Gap between Quantum Chemistry and Molecular Simulations Chem. Rev. 2000, 100, 4087-4108
15. Donchev, A. G.; Ozrin, V. D.; Subbotin, M. V.; Tarasov, O. V.; Tarasov, V. I. A Quantum Mechanical Polarizable Force Field for Biomolecular Interactions Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 7829-7834
16. Torheyden, M.; Jansen, G. A New Potential Energy Surface for the Water Dimer Obtained from Separate Fits of Ab Initio Electrostatic, Induction, Dispersion and Exchange Energy Contributions Mol. Phys. 2006, 104, 2101-2138
17. Podeszwa, R.; Bukowski, R.; Szalewicz, K. Potential Energy Surface For the Benzene Dimer and Perturbational Analysis of π-π Interactions J. Phys. Chem. A 2006, 110, 10345-10354
18. Li, X.; Volkov, A. V.; Szalewicz, K.; Coppens, P. Interaction Energies between Glycopeptide Antibiotics and Substrates in Complexes Determined by X-ray Crystallography: Application of a Theoretical Databank of Aspherical Atoms and a Symmetry-Adapted Perturbation Theory-Based Set of Interatomic Potentials Acta Crystallogr., Sect. D: Biol. Crystallogr. 2006, 62, 639-647
19. Hellmann, R.; Bich, E.; Vogel, E. Ab Initio Intermolecular Potential Energy Surface and Second Pressure Virial Coefficients of Methane J. Chem. Phys. 2008, 128, 214303
20. Szalewicz, K.; Leforestier, C.; van der Avoird, A. Towards the Complete Understanding of Water by a First-Principles Computational Approach Chem. Phys. Lett. 2009, 482, 1-14
21. Archambault, F.; Chipot, C.; Soteras, I.; Javier Luque, F.; Schulten, K.; Dehez, F. Polarizable Intermolecular Potentials for Water and Benzene Interacting with Halide and Metal Ions J. Chem. Theory Comput. 2009, 5, 3022-3031
22. Wang, B.; Truhlar, D. G. Including Charge Penetration Effects in Molecular Modeling J. Chem. Theory Comput. 2010, 6, 3330-3342
23. Totton, T. S.; Misquitta, A. J.; Kraft, M. A First Principles Development of a General Anisotropic Potential for Polycyclic Aromatic Hydrocarbons J. Chem. Theory Comput. 2010, 6, 683-695
24. Wu, J. C.; Piquemal, J.-P.; Chaudret, R.; Reinhardt, P.; Ren, P. Polarizable Molecular Dynamics Simulation of Zn(II) in Water Using the AMOEBA Force Field J. Chem. Theory Comput. 2010, 6, 2059-2070
25. Boese, A. D.; Forbert, H.; Masia, M.; Tekin, A.; Marx, D.; Jansen, G. Constructing Simple Yet Accurate Potentials For Describing the Solvation of HCl/Water Clusters in Bulk Helium and Nanodroplets Phys. Chem. Chem. Phys. 2011, 13, 14550-14564
26. Leforestier, C.; Tekin, A.; Jansen, G.; Herman, M. First Principles Potential for the Acetylene Dimer and Refinement by Fitting to Experiments J. Chem. Phys. 2011, 135, 234306
27. Taylor, D. E.; Rob, F.; Rice, B. M.; Podeszwa, R.; Szalewicz, K. A Molecular Dynamics Study of 1,1-diamino-2,2-dinitroethylene (FOX-7) Crystal Using a Symmetry Adapted Perturbation Theory-Based Intermolecular Force Field Phys. Chem. Chem. Phys. 2011, 13, 16629-16636
28. Tafipolsky, M.; Engels, B. Accurate Intermolecular Potentials with Physically Grounded Electrostatics J. Chem. Theory Comput. 2011, 7, 1791-1803
29. McDaniel, J. G.; Schmidt, J. R. Physically-Motivated Force Fields from Symmetry-Adapted Perturbation Theory J. Phys. Chem. A 2013, 117, 2053-2066
30. Yokogawa, D. Development of the Isotropic Site-Site Potential for Exchange Repulsion Energy and Combination with the Isotropic Site-Site Potential for Electrostatic Part J. Chem. Phys. 2012, 137, 204101
31. Wang, L.-P.; Chen, J.; Van Voorhis, T. Systematic Parametrization of Polarizable Force Fields from Quantum Chemistry Data J. Chem. Theory Comput. 2013, 9, 452-460
32. Misquitta, A. J.; Stone, A. J. Accurate Induction Energies for Small Organic Molecules: 1. Theory J. Chem. Theory Comput. 2008, 4, 7-18
33. Misquitta, A. J.; Stone, A. J.; Price, S. L. Accurate Induction Energies for Small Organic Molecules. 2. Development and Testing of Distributed Polarizability Models against SAPT(DFT) Energies J. Chem. Theory Comput. 2008, 4, 19-32
34. Holt, A.; Boström, J.; Karlström, G.; Lindh, R. A NEMO Potential that Includes the Dipole-Quadrupole and Quadrupole-Quadrupole Polarizability J. Comput. Chem. 2010, 31, 1583-1591
35. Arnautova, Y. A.; Jagielska, A.; Pillardy, J.; Scheraga, H. A. Derivation of a New Force Field for Crystal-Structure Prediction Using Global Optimization: Nonbonded Potential Parameters for Hydrocarbons and Alcohols J. Phys. Chem. B 2003, 107, 7143-7154
36. Bordner, A. J.; Cavasotto, C. N.; Abagyan, R. A. Direct Derivation of van der Waals Force Field Parameters from Quantum Mechanical Interaction Energies J. Phys. Chem. B 2003, 107, 9601-9609
37. Hayes, J. M.; Greer, J. C.; Morton-Blake, D. A. A Force-Field Description of Short-Range Repulsions for High Density Alkane Molecular Dynamics, Simulations J. Comput. Chem. 2004, 25, 1953-1966
38. Tsuzuki, S.; Uchimaru, T.; Tanabe, K.; Kuwajima, S. Refinement of Nonbonding Interaction Potential Parameters for Methane on the Basis of the Pair Potential Obtained by MP3/6-311G(3d,3p)-Level Ab-Initio Molecular-Orbital Calculations-the Anisotropy of H/H Interaction J. Phys. Chem. 1994, 98, 1830-1833
39. Wheatley, R. J.; Mitchell, J. B. O. Gaussian Multipoles in Practice-Electrostatic Energies for Intermolecular Potentials J. Comput. Chem. 1994, 15, 1187-1198
40. Kairys, V.; Jensen, J. H. Evaluation of the Charge Penetration Energy between Non-orthogonal Molecular Orbitals Using the Spherical Gaussian Overlap Approximation Chem. Phys. Lett. 1999, 315, 140-144
41. Spackman, M. A. The Use of the Promolecular Charge Density to Approximate the Penetration Contribution to Intermolecular Electrostatic Energies Chem. Phys. Lett. 2006, 418, 158-162
42. Donchev, A. G. Ab Initio Quantum Force Field for Simulations of Nanostructures Phys. Rev. B 2006, 74, 235401
43. Rob, F.; Podeszwa, R.; Szalewicz, K. Electrostatic Interaction Energies with Overlap Effects from a Localized Approach Chem. Phys. Lett. 2007, 445, 315-320
44. Fraschini, E.; Stone, A. J. H-H Model Potential for Exchange-Repulsion Energy of Methane Dimer J. Comput. Chem. 1998, 19, 847-857
45. Stone, A. J.; Misquitta, A. J. Atom-Atom Potentials from Ab Initio Calculations Int. Rev. Phys. Chem. 2007, 26, 193-222
46. Sokalski, W. A.; Lowrey, A. H.; Roszak, S.; Lewchenko, V.; Blaisdell, J.; Hariharan, P. C.; Kaufman, J. J. Nonempirical Atom-Atom Potentials for Main Components of Intermolecular Interaction Energy J. Comput. Chem. 1986, 7, 693-700
47. Ma, J. C.; Dougherty, D. A. The Cation-π Interaction Chem. Rev. 1997, 97, 1303-1324
48. Salonen, L. M.; Ellermann, M.; Diederich, F. Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures Angew. Chem., Int. Ed. 2011, 50, 4808-4842
49. Kim, K. S.; Tarakeshwar, P.; Lee, J. Y. Molecular Clusters of π-Systems: Theoretical Studies of Structures, Spectra, and Origin of Interaction Energies Chem. Rev. 2000, 100, 4145-4186
50. Dougherty, D. A. The Cation-π Interaction Acc. Chem. Res. 2013, 46, 885-893
51. Ponder, J. W.; Wu, C.-J.; Ren, P.-Y.; Pande, V. S.; Chodera, J. D.; Schnieders, M. J.; Haque, I.; Mobley, D. L.; Lambrecht, D. S.; DiStasio, R. A., Jr. Current Status of the AMOEBA Polarizable Force Field J. Phys. Chem. B 2010, 114, 2549-2564
52. Cubero, E.; Luque, F. J.; Orozco, M. Is Polarization Important in Cation-π Interactions? Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 5976-5980
53. Kim, D.; Hu, S.; Tarakeshwar, P.; Kim, K. S.; Lisy, J. M. Cation-π Interactions: A Theoretical Investigation of the Interaction of Metallic and Organic Cations with Alkenes, Arenes, and Heteroarenes J. Phys. Chem. A 2003, 107, 1228-1238
54. Pratuangdejkul, J.; Jaudon, P.; Ducrocq, C.; Nosoongnoen, W.; Guerin, G. A.; Conti, M.; Loric, S.; Launay, J. M.; Manivet, P. Cation-π Interactions in Serotonin: Conformational, Electronic Distribution, and Energy Decomposition Analysis J. Chem. Theory Comput. 2006, 2, 746-760
55. Soteras, I.; Orozco, M.; Luque, F. J. Induction Effects in Metal Cation-Benzene Complexes Phys. Chem. Chem. Phys. 2008, 10, 2616-2624
56. Marshall, M. S.; Steele, R. P.; Thanthiriwatte, K. S.; Sherrill, C. D. Potential Energy Curves for Cation-π Interactions: Off-Axis Configurations Are Also Attractive J. Phys. Chem. A 2009, 113, 13628-13632
57. Orabi, E. A.; Lamoureux, G. Cation-π and π-π Interactions in Aqueous Solution Studied Using Polarizable Potential Models J. Chem. Theory Comput. 2012, 8, 182-193
58. Zheng, X.; Wu, C.; Ponder, J. W.; Marshall, G. R. Molecular Dynamics of β-Hairpin Models of Epigenetic Recognition Motifs J. Am. Chem. Soc. 2012, 134, 15970-15978
59. Polly, R.; Werner, H. J.; Manby, F. R.; Knowles, P. J. Fast Hartree-Fock Theory Using Local Density Fitting Approximations Mol. Phys. 2004, 102, 2311-2321
60. Werner, H.-J.; Knowles, P. J.; Knizia, G.; Manby, F. R.; M. Schütz MOLPRO, version 2010.1, a package of ab initio programs; see http://www.molpro.net.
61. Werner, H.-J.; Knowles, P. J.; Knizia, G.; Manby, F. R.; Schütz, M. Molpro: a General-Purpose Quantum Chemistry Program Package Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2, 242-253
62. Dunning, T. H. Gaussian-Basis Sets for Use in Correlated Molecular Calculations. 1. The Atoms Boron Through Neon and Hydrogen J. Chem. Phys. 1989, 90, 1007-1023
63. Weigend, F. A Fully Direct RI-HF Algorithm: Implementation, Optimised Auxiliary Basis Sets, Demonstration of Accuracy and Efficiency Phys. Chem. Chem. Phys. 2002, 4, 4285-4291
64. Weigend, F.; Köhn, A.; Hättig, C. Efficient Use of the Correlation Consistent Basis Sets in Resolution of the Identity MP2 Calculations J. Chem. Phys. 2002, 116, 3175-3183
65. Grüning, M.; Gritsenko, O. V.; van Gisbergen, S. J. A.; Baerends, E. J. Shape Corrections to Exchange-Correlation Potentials by Gradient-Regulated Seamless Connection of Model Potentials for Inner and Outer Region J. Chem. Phys. 2001, 114, 652-660
66. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
67. Adamo, C.; Barone, V. Toward Reliable Density Functional Methods Without Adjustable Parameters: The PBE0Model J. Chem. Phys. 1999, 110, 6158-6170
68. Lias, S. G. Ionization Energy Evaluation. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P.J.,; Mallard, W.G., Eds.; National Institute of Standards and Technology: Gaithersburg MD, 2011; http://webbook.nist.gov (retrieved February 7, 2013).
69. Moszynski, R.; Heijmen, T. G. A.; Jeziorski, B. Symmetry-Adapted Perturbation Theory for the Calculation of Hartree-Fock Interaction Energies Mol. Phys. 1996, 88, 741-758
70. Heßelmann, A. Comparison of Intermolecular Interaction Energies from SAPT and DFT Including Empirical Dispersion Contributions J. Phys. Chem. A 2011, 115, 11321-11330
71. Podeszwa, R.; Cencek, W.; Szalewicz, K. Efficient Calculations of Dispersion Energies for Nanoscale Systems from Coupled Density Response Functions J. Chem. Theory Comput. 2012, 8, 1963-1969
72. Singh, N. J.; Min, S. K.; Kim, D. Y.; Kim, K. S. Comprehensive Energy Analysis for Various Types of π-Interaction J. Chem. Theory Comput. 2009, 5, 515-529
73. Boys, S. F.; Bernardi, F. Calculation of Small Molecular Interactions by Differences of Separate Total Energies-Some Procedures with Reduced Errors Mol. Phys. 1970, 19, 553-566
74. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gaussian 09, Revision B.01; Gaussian Inc.: Wallingford, CT, 2010.
75. Stone, A. J. Distributed Multipole Analysis: Stability for Large Basis Sets. J. Chem. Theory Comput. 2005, 1, 1128-1132; GDMA 2.2.04 at http://www-stone.ch.cam.ac.uk/programs.html.
76. Halgren, T. A. Representation of van der Waals (vdW) Interactions in Molecular Mechanics Force Fields: Potential Form, Combination Rules, and vdW Parameters J. Am. Chem. Soc. 1992, 114, 7827-7843
77. Charbonneau, P. Genetic Algorithms in Astronomy and Astrophysics. Astrophys. J., Suppl. Ser. 1995, 101, 309-334; PIKAIA 1.2 at http://www.hao.ucar.edu/modeling/pikaia/pikaia.php.
78. Ren, P.-Y.; Wu, C.-J.; Ponder, J. W. Polarizable Atomic Multipole-Based Molecular Mechanics for Organic Molecules J. Chem. Theory Comput. 2011, 7, 3143-3161
79. Sa, R. J.; Zhu, W. L.; Shen, J. H.; Gong, Z.; Cheng, J. G.; Chen, K. X.; Jiang, H. L. How Does Ammonium Dynamically Interact with Benzene in Aqueous Media? A First Principle Study Using the Car-Parrinello Molecular Dynamics Method J. Phys. Chem. B 2006, 110, 5094-5098
80. +] Interactions with the Aromatic Motifs of Naturally Occurring Amino Acids: A Theoretical Study J. Phys. Chem. A 2005, 109, 8893-8903
81. Dehez, F.; Angyan, J. G.; Gutierrez, I. S.; Luque, F. J.; Schulten, K.; Chipot, C. Modeling Induction Phenomena in Intermolecular Interactions with an Ab Initio Force Field J. Chem. Theory Comput. 2007, 3, 1914-1926
82. Wang, Z.-X.; Zhang, J.-C.; Cao, W.-L. Study on the Cation-π Interactions between Ammonium Ion and Aromatic π Systems Chin. J. Chem. 2006, 24, 1523-1530
83. Mo, Y.; Bao, P.; Gao, J. L. Energy Decomposition Analysis Based on a Block-Localized Wavefunction and Multistate Density Functional Theory Phys. Chem. Chem. Phys. 2011, 13, 6760-6775
84. Aschi, M.; Mazza, F.; Di Nola, A. Cation-π Interactions between Ammonium Ion and Aromatic Rings: an Energy Decomposition Study THEOCHEM 2002, 587, 177-188
85. Voisin, C.; Cartier, A.; Rivail, J. L. Computation of Accurate Electronic Molecular Polarizabilities J. Phys. Chem. 1992, 96, 7966-7971
86. Ponder, J. W.; Ren, P.; Pappu, R. V.; Hart, R. K.; Hodgson, M. E.; Cistola, D. P.; Kundrot, C. E.;; Richards, F. M. Tinker software tools for molecular design, version 5.1; Washington University School of Medicine: St. Louis, MO, February 2010; at http://dasher.wustl.edu/tinker/.
87. Elking, D.; Darden, T.; Woods, R. J. Gaussian Induced Dipole Polarization Model J. Comput. Chem. 2007, 28, 1261-1274
88. Kim, H. W.; Rhee, Y. M. Molecule-Specific Determination of Atomic Polarizabilities with the Polarizable Atomic Multipole Model J. Comput. Chem. 2012, 33, 1662-1672
89. Patkowski, K.; Szalewicz, K.; Jeziorski, B. Orbital Relaxation and the Third-Order Induction Energy in Symmetry-Adapted Perturbation Theory Theor. Chem. Acc. 2010, 127, 211-221
90. Lao, K. U.; Herbert, J. M. Breakdown of the Single-Exchange Approximation in Third-Order Symmetry-Adapted Perturbation Theory J. Phys. Chem. A 2012, 116, 3042-3047
91. Schäffer, R.; Jansen, G. Intermolecular Exchange-Induction Energies Without Overlap Expansion Theor. Chem. Acc. 2012, 131, 1235
92. Hobza, P. Calculations on Noncovalent Interactions and Databases of Benchmark Interaction Energies Acc. Chem. Res. 2012, 45, 663-672
93. Martinez, C. R.; Iverson, B. L. Rethinking the Term "pi- stacking" Chem. Sci. 2012, 3, 2191-2201