Dispersion-corrected density functional theory for aromatic interactions in complex systems

Accounts of Chemical Research

Volumn 46, Issue 4, 2013, Pages 916-926

  Ehrlich, Stephan ^a   Moellmann, Jonas ^a   Grimme, Stefan ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84876268668     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar3000844     Document Type: Article

References (75)

1. Kaplan, I. G. Intermolecular Interactions; J. Wiley & Sons: Chichester, U.K., 2006.
2. Meyer, E. A.; Castellano, R. K.; Diederich, F. Interactions with Aromatic Rings in Chemical and Biological Recognition Angew. Chem., Int. Ed. 2003, 42, 1210-1250
3. Kannan, N.; Vishveshwara, S. Aromatic Clusters: A Determinant of Thermal Stability of Thermophilic Proteins Protein Eng. 2000, 13, 753-761
4. Hobza, P. Noncovalent Interactions in Biochemistry WIREs Comput. Mol. Sci. 2011, 1, 3-17
5. Hohenstein, E. G.; Sherrill, C. D. Wavefunction Methods for Noncovalent Interactions WIREs Comput. Mol. Sci. 2012, 2, 304-326
6. Cremer, D. Møller-Plesset Perturbation Theory: From Small Molecule Methods to Methods for Thousands of Atoms WIREs Comput. Mol. Sci. 2011, 1, 509-530
7. Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. Origin of Attraction and Directionality of the π/π Interaction: Model Chemistry Calculations of Benzene Dimer Interaction J. Am. Chem. Soc. 2002, 124, 104-112
8. Grimme, S. Do Special Noncovalent π-π Stacking Interactions Really Exist? Angew. Chem., Int. Ed. 2008, 47, 3430-3434
9. Pérez-Jordá, J. M.; Becke, A. D. A Density-Functional Study of van der Waals Forces: Rare Gas Diatomics Chem. Phys. Lett. 1995, 233, 134-137
10. Kristyán, S.; Pulay, P. Can (Semi)Local Density Functional Theory Account for the London Dispersion Forces? Chem. Phys. Lett. 1994, 229, 175-180
11. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A Consistent and Accurate Ab Initio Parametrization of Density Functional Dispersion Correction (DFT-D) for the 94 Elements H-Pu J. Chem. Phys. 2010, 132 154104
12. Becke, A. D.; Johnson, E. R. Exchange-Hole Dipole Moment and the Dispersion Interaction J. Chem. Phys. 2005, 122 154104
13. Tkatchenko, A.; Scheffler, M. Accurate Molecular Van Der Waals Interactions from Ground-State Electron Density and Free-Atom Reference Data Phys. Rev. Lett. 2009, 102 073005
14. Hujo, W.; Grimme, S. Performance of the van der Waals Density Functional VV10 and (hybrid) GGA Variants for Thermochemistry and Noncovalent Interactions J. Chem. Theory Comput. 2011, 7, 3866-3871
15. Dion, M.; Rydberg, H.; Schröder, E.; Langreth, D. C.; Lundqvist, B. I. Van der Waals Density Functional for General Geometries Phys. Rev. Lett. 2004, 92 246401
16. Burns, L. A.; Vazquez-Mayagoitia, A.; Sumpter, B. G.; Sherrill, C. D. A Comparison of Dispersion Corrections (DFT-D), Exchange-Hole Dipole Moment (XDM) Theory, and Specialized Functionals J. Chem. Phys. 2011, 134 084107
17. Grimme, S. Density Functional Theory with London Dispersion Corrections WIREs Comput. Mol. Sci. 2011, 1, 211-228
18. Jurecka, P.; Sponer, J.; Cerny, J.; Hobza, P. Benchmark Database of Accurate (MP2 and CCSD(T) Complete Basis Set Limit) Interaction Energies of Small Model Complexes, DNA Base Pairs, and Amino Acid Pairs Phys. Chem. Chem. Phys. 2006, 8, 1985-1993
19. Řezáč, J.; Riley, K. E.; Hobza, P. S66: A Well-Balanced Database of Benchmark Interaction Energies Relevant to Biomolecular Structures J. Chem. Theory Comput. 2011, 7, 2427
20. Goerigk, L.; Grimme, S. A Thorough Benchmark of Density Functional Methods for General Main Group Thermochemistry, Kinetics, And Noncovalent Interactions Phys. Chem. Chem. Phys. 2011, 13, 6670-6688
21. Grimme, S.; Djukic, J. P. Cation-Cation "Attraction": When London Dispersion Attraction Wins over Coulomb Repulsion Inorg. Chem. 2011, 50, 2619-2628
22. Atwood, J. L.; Steed, J. W. Supramolecular Chemistry; Wiley: Chichester, U.K., 2009.
23. Schneider, H.-J. Binding Mechanisms in Supramolecular Complexes Angew. Chem., Int. Ed. 2009, 48, 3924-3977
24. Raju, R. K.; Bloom, J. W. G.; An, Y.; Wheeler, S. E. Substituent Effects on Non-Covalent Interactions with Aromatic Rings: Insights from Computational Chemistry ChemPhysChem 2011, 12, 3116-3130
25. Branchi, B.; Balzani, V.; Ceroni, P.; Kuchenbrandt, M. C.; Klärner, F.-G.; Bläser, D.; Boese, R. Molecular Clips with Extended Aromatic Sidewalls as Receptors for Electron- Acceptor Molecules. Synthesis and NMR, Photophysical, and Electrochemical Properties J. Org. Chem. 2008, 73, 5839-5851
26. Kruse, H.; Grimme, S. A Geometrical Correction for the Inter- and Intramolecular Basis Set Superposition Error in Hartree-Fock and Density Functional Theory Calculations for Large Systems J. Chem. Phys. 2012, 136, 154101
27. Grimme, S. Semiempirical Hybrid Density Functional with Perturbative Second-Order Correlation J. Chem. Phys. 2006, 124, 034108
28. Boys, S. F.; Bernardi, F. The Calculation of Small Molecular Interactions by the Differences of Separate Total Energies. Some Procedures with Reduced Errors Mol. Phys. 1970, 19, 553-566
29. Weigend, F.; Ahlrichs, R. Balanced Basis Sets of Split Valence, Triple Zeta Valence and Quadruple Zeta Valence Quality for H to Rn: Design and Assessment of Accuracy Phys. Chem. Chem. Phys. 2005, 7, 3297-3305
30. Grimme, S.; Ehrlich, S.; Goerigk, L. Effect of the Damping Function in Dispersion Corrected Density Functional Theory J. Comput. Chem. 2011, 32, 1456-1465
31. Goerigk, L.; Kruse, H.; Grimme, S. Benchmarking Density Functional Methods against the S66 and S66 × 8 Datasets for Non-Covalent Interactions ChemPhysChem 2011, 12, 3421-3433
32. Antony, J.; Grimme, S.; Liakos, D. G.; Neese, F. Protein-Ligand Interaction Energies with Dispersion Corrected Density Functional Theory and High-Level Wave Function Based Methods J. Phys. Chem. A 2011, 115, 11210-11220
33. Vydrov, O. A.; Van Voorhis, T. Nonlocal van der Waals Density Functional: The Simpler the Better J. Chem. Phys. 2010, 133 244103
34. Hujo, W.; Grimme, S. Comparison of the Performance of Dispersion-Corrected Density Functional Theory for Weak Hydrogen Bonds Phys. Chem. Chem. Phys. 2011, 13, 13942-13950
35. Grimme, S.; Hujo, W.; Kirchner, B. Performance of Dispersion-Corrected Density Functional Theory for the Interactions in Ionic Liquids Phys. Chem. Chem. Phys. 2012, 14, 4875-4883
36. Tao, J.; Perdew, J. P.; Staroverov, V. N.; Scuseria, G. E. Climbing the Density Functional Ladder: Nonempirical Meta Generalized Gradient Approximation Designed for Molecules and Solids Phys. Rev. Lett. 2003, 91, 146401
37. Zhang, Y.; Yang, W. Comment on "Generalized Gradient Approximation Made Simple" Phys. Rev. Lett. 1998, 80, 890
38. Zhao, Y.; Truhlar, D. G. Design of Density Functionals That Are Broadly Accurate for Thermochemistry, Thermochemical Kinetics, and Nonbonded Interactions J. Phys. Chem. A 2005, 109, 5656-5667
39. 2O Chem. Phys. Lett. 1998, 286, 243
40. Halkier, A.; Helgaker, T.; Jørgensen, P.; Klopper, W.; Olsen, J. Basis-Set Convergence of the Energy in Molecular Hartree-Fock Calculations Chem. Phys. Lett. 1999, 302, 437-446
41. Dunning, T. H., Jr. Gaussian Basis Sets for Use in Correlated Molecular Calculations. I. The Atoms Boron through Neon and Hydrogen J. Chem. Phys. 1989, 90, 1007-1023
42. Kendall, R. A.; Dunning, T. H.; Harrison, R. J. Electron Affinities of the First-Row Atoms Revisited. Systematic Basis Sets and Wave Functions J. Chem. Phys. 1992, 96, 6796-6806
43. Marshall, M. S.; Burns, L. A.; Sherrill, C. D. Basis Set Convergence of the Coupled-Cluster Correction, d CCSD (T) MP 2: Best Practices for Benchmarking Non-Covalent Interactions and the Attendant Revision of the S22, NBC10 and HSG Databases J. Chem. Phys. 2011, 135 194102
44. Šponer, J.; Riley, K. E.; Hobza, P. Nature and Magnitude of Aromatic Stacking of Nucleic Acid Bases Phys. Chem. Chem. Phys. 2008, 10, 2595-2610
45. Tsuzuki, S.; Uchimaro, T.; Mikami, M. Intermolecular Interaction between Hexafluorobenzene and Benzene: Ab Initio Calculations Including CCSD(T) Level Electron Correction J. Phys. Chem. A 2006, 110, 2027-2033
46. 5X Stacking Interactions J. Org. Chem. 2006, 71, 9261-9270
47. Wheeler, S. E.; Houk, K. N. Substituent Effects in the Benzene Dimer are Due to Direct Interactions of the Substituents with the Unsubstituted Benzene J. Am. Chem. Soc. 2008, 130, 10854-10855 PMID 18652453
48. Wheeler, S. E. Local Nature of Substituent Effects in Stacking Interactions J. Am. Chem. Soc. 2011, 133, 10262-10274
49. Kitaura, K.; Morokuma, K. A New Energy Decomposition Scheme for Molecular Interactions within the Hartree-Fock Approximation Int. J. Quantum Chem. 1976, 10, 325-340
50. Heßelmann, A.; Jansen, G.; Schütz, 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
51. Hohenstein, E. G.; Sherrill, C. D. Density Fitting and Cholesky Decomposition Approximations in Symmetry-Adapted Perturbation Theory: Implementation and Application to Probe the Nature of π-π Interactions in Linear Acenes J. Chem. Phys. 2010, 132 184111
52. Grimme, S. Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction J. Comput. Chem. 2006, 27, 1787-1799
53. Grimme, S.; Mück-Lichtenfeld, C.; Antony, J. Noncovalent Interactions between Graphene Sheets and in Multishell (Hyper)Fullerenes J. Phys. Chem. C 2007, 111, 11199-11207
54. Mück-Lichtenfeld, C.; Grimme, S. Structure and Binding Energies of the Porphine Dimer Mol. Phys. 2007, 105, 2793-2798
55. Janowski, T.; Ford, A. R.; Pulay, P. Accurate Correlated Calculation of the Intermolecular Potential Surface in the Coronene Dimer Mol. Phys. 2010, 108, 249-257
56. Grimme, S. Improved Second-Order Møller.Plesset Perturbation Theory by Separate Scaling of Parallel- And Antiparallel-Spin Pair Correlation Energies J. Chem. Phys. 2003, 118, 9095-9102
57. Cybulski, S. M.; Lytle, M. L. The Origin of Deficiency of the Supermolecule Second-Order Møller-Plesset Approach for Evaluation Interaction Energies J. Chem. Phys. 2007, 127 141102
58. Kano, K.; Minamizono, H.; Kitae, T.; Negi, S. Self-Aggregation of Cationic Porphyrins in Water. Can π-π Stacking Interaction Overcome Electrostatic Repulsive Force? J. Phys. Chem. A 1997, 101, 6118-6124
59. Grimme, S. Supramolecular Binding Thermodynamics by Dispersion Corrected Density Functional Theory Chem.-Eur. J. 2012, DOI: 10.1002/chem.201200497
60. Klamt, A.; Schüürmann, G. COSMO: A New Approach to Dielectric Screening in Solvents with Explicit Expressions for the Screening Energy and Its Gradient J. Chem. Soc., Perkin Trans. 2 1993, 799-805
61. Klamt, A. The COSMO and COSMO-RS Solvation Models WIREs Comput. Mol. Sci. 2011, 1, 699-709
62. Stewart, J. J. P. Optimization of Parameters for Semiempirical Methods V: Modification of NDDO Approximations and Application to 70 Elements J. Mol. Mod. 2007, 13, 1173
63. Shen, Y.; Chen, C.-F. Helicenes: Synthesis and Applications Chem. Rev. 2012, 112, 1463-1535
64. Bucko, T.; Hafner, J.; Lebegue, S.; Angyan, J. G. Improved Description of the Structure of Molecular and Layered Crystals: Ab Initio DFT Calculations with van der Waals Corrections J. Phys. Chem. A 2010, 114, 11814-11824
65. Allen, F. H. The Cambridge Structural Database: A Quarter of a Million Crystal Structures and Rising Acta Crystallogr. 2002, B58, 380-388 Available under CSD-code HEXHEL
66. Moellmann, J.; Grimme, S. Importance of London Dispersion Effects for the Packing of Molecular Crystals: A Case Study for Intramolecular Stacking in a Bis-thiophene Derivative Phys. Chem. Chem. Phys. 2010, 12, 8500
67. Roux, M. V.; Temprado, M.; Chickos, J. S.; Nagano, Y. Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons J. Phys. Chem. Ref. Data 2008, 37, 1855
68. TURBOMOLE: R. Ahlrichs et al., Universität Karlsruhe 2009. See http://www.turbomole.com.
69. Neese, F. ORCA-an ab initio, density functional and semiempirical program package, Ver. 2.9 (Rev 0), Max Planck Institute for Bioinorganic Chemistry, Germany, 2011.
70. Werner, H.-J. MOLPRO, version 2006.1, a package of ab initio programs. see http://www.molpro.net.
71. Stewart, J. J. P. Stewart Computational Chemistry, Version 11.038L, see http://OpenMOPAC.net.
72. Kresse, G.; Furthmüller, J. Efficiency of Ab-Initio Total Energy Calculations for Metals and Semiconductors Using a Plane-Wave Basis Set J. Comp. Mat. Sci. 1996, 6, 15
73. Kresse, G.; Joubert, J. From Ultrasoft Pseudopotentials to the Projector Augmented-Wave Method Phys. Rev. B 1999, 59, 1758
74. Vahtras, O.; Almlöf, J.; Feyereisen, M. W. Integral Approximations for LCAO-SCF Calculations Chem. Phys. Lett. 1993, 213, 514-518
75. Weigend, F.; Häser, M. RI-MP2: First Derivatives and Global Consistency Theor. Chem. Acc. 1997, 97, 331-340