Why is the L-shaped structure of X2··· X2 (X = F, Cl, Br, I) complexes more stable than other structures?

Journal of Physical Chemistry A

Volumn 118, Issue 21, 2014, Pages 3846-3855

  Sedlak, Robert ^a   Deepa, Palanisamy ^a   Hobza, Pavel ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; DISPERSIONS;

DIFFERENT STRUCTURE; DISPERSION ENERGIES; ELECTROSTATIC ENERGIES; ELECTROSTATIC POTENTIALS; L-SHAPED STRUCTURE; QUADRUPOLE MOMENTS; STABILIZATION ENERGY; STABLE STRUCTURES;

DIMERS;

EID: 84901659739     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp502648e     Document Type: Article

References (70)

1. 2 Molecules: The Description of Charge-Shift Bonding within the Generalized Valence Bond Ansatz Theor. Chem. Acc. 2009, 122, 51-66
2. Munusamy, E.; Sedlak, R.; Hobza, P. On The Nature of the Stabilization of Benzene···Dihalogen and Benzene··· Dinitrogen Complexes: CCSD(T)/CBS and DFT-SAPT Calculations ChemPhysChem 2011, 12, 3253-3261
3. Politzer, P.; Murray, J. S.; Clark, T. Halogen Bonding: An Electrostatically Driven Highly Directional Noncovalent Interaction Phys. Chem. Chem. Phys. 2010, 12, 7748-7757
4. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. Halogen Bonding: The σ-Hole J. Mol. Model. 2007, 13, 291-296
5. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. An Overview of Halogen Bonding J. Mol. Model. 2007, 13, 305-311 (Pubitemid 46189160)
6. Desiraju, G. R.; Shing Ho, P.; Kloo, L.; Legon, A. C.; Marquardt, R.; Metrangolo, P.; Politzer, P.; Resnati, G.; Rissanen, K. Definition of the Halogen Bond Pure Appl. Chem. 2013, 85, 1711-1713
7. Muller, P. Glossary of Terms Used in Physical Organic Chemistry Pure Appl. Chem. 1994, 66, 1077-1184
8. Duarte, D. J. R.; Angelina, E. L.; Peruchena, N. M. On the Strength of the Halogen Bonds: Mutual Penetration, Atomic Quadrupole Moment and Laplacian Distribution of the Charge Density Analysis Comput. Theor. Chem. 2012, 998, 164-172
9. Politzer, P.; Laurence, P. R.; Jayasuriya, K. Molecular Electrostatic Potentials: An Effective Tool for the Elucidation of Biochemical Phenomena Environ. Health Perspect. 1985, 61, 191-202 (Pubitemid 16221999)
10. Murray, J. S.; Politzer, P. Statistical Analysis of the Molecular Surface Electrostatic Potential: An Approach to Describing Noncovalent Interactions in Condensed Phases J. Mol. Struct.: THEOCHEM 1998, 425, 107-114 (Pubitemid 128392566)
11. Politzer, P.; Murray, J. S. Representation of Condensed Phase Properties in Terms of Molecular Surface Electrostatic Potentials Trends Chem. Phys. 1999, 7, 157-168
12. Politzer, P.; Murray, J. S.; Peralta-Inga, Z. Molecular Surface Electrostatic Potentials in Relation to Noncovalent Interactions in Biological Systems Int. J. Quantum Chem. 2001, 85, 676-684 (Pubitemid 33105812)
13. Becke, A. D. Density-Functional Thermochemistry. V. Systematic Optimization of Exchange-correlation Functionals J. Chem. Phys. 1997, 107, 8554-8560 (Pubitemid 127611634)
14. Schmider, H. L.; Becke, A. D. Optimized Density Functionals from the Extended G2 Test Set J. Chem. Phys. 1998, 108, 9624-9631 (Pubitemid 128600156)
15. Hartree, D. R. The Wave Mechanics of an Atom with a Non-Coulomb Central Field. Part I. Theory and Methods Math. Proc. Cambridge Philos. Soc. 1928, 24, 89-110
16. Fock, V. Näherungsmethode zur Lösung des quantenmechanischen Mehrkörperproblems Z. Phys. 1930, 61, 126-148
17. 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
18. Davidson, E. R. Comment on Comment on Dunnings Correlation-Consistent Basis Sets Chem. Phys. Lett. 1996, 260, 514-518
19. Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. Electron Affinities of the First-Row Atoms Revisited. Systematic Basis Sets and Wave Functions J. Chem. Phys. 1992, 96, 6796-6806
20. Woon, D. E.; Dunning, T. H., Jr. Gaussian-Basis Sets for Use in Correlated Molecular Calculations. 3. The Atoms Aluminum Through Argon J. Chem. Phys. 1993, 98, 1358-1371
21. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-68 (Pubitemid 126631804)
22. Perdew, J. P.; Burke, K.; Ernzerhof, M. Errata: Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1997, 78, 1396
23. Adamo, C.; Barone, V. Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0 Model J. Chem. Phys. 1999, 110, 6158-6169
24. Møller, C.; Plesset, M. S. Note on an Approximation Treatment for Many-Electron Systems Phys. Rev. 1934, 46, 618-622
25. Pople, J. A.; Seeger, R.; Krishnan, R. Variational Configuration Interaction Methods and Comparison with Perturbation Theory Int. J. Quantum Chem. 1977, 12 (Suppl. S11) 149-163
26. Bader, R. F. W.; Carroll, M. T.; Cheeseman, J. R.; Chang, C. Properties of Atoms in Molecules: Atomic Volumes J. Am. Chem. Soc. 1987, 109, 7968-7979
27. Kolár, J.; Hobza, P. The Strength and Directonality of the Halogen Bond Are Co-Determined by the Magnitude and Size of the σ-Hole Phys. Chem. Chem. Phys. 2014, 16, 9987-9996
28. Pitonak, M.; Riley, K. E.; Neogrady, P.; Hobza, P. Highly Accurate CCSD(T) and DFT-SAPT Stabilization Energies of H-Bonded and Stacked Structures of the Uracil Dimer ChemPhysChem 2008, 9, 1636-1644
29. Zierkiewicz, W.; Michalska, D.; Hobza, P. Adenine Ribbon Stabilized by Watson-Crick and Hoogsteen Hydrogen Bonds: WFT and DFT Study Phys. Chem. Chem. Phys. 2010, 12, 2888-2894
30. Rezac, J.; Hobza, P. Extrapolation and Scaling of the DFT-SAPT Interaction Energies toward the Basis Set Limit J. Chem. Theory Comput. 2011, 7, 685-689
31. Ran, J.; Hobza, P. Nature of Bonding in Nine Planar Hydrogen-Bonded Adenine···Thymine Base Pairs J. Phys. Chem. B 2009, 113, 2933-2936
32. Riley, K. E.; Pitonak, M.; Cerny, J.; Hobza, P. On the Structure and Geometry of Biomolecular Binding Motifs (Hydrogen-bonding, Stacking, X-H···π): WFT and DFT Calculations J. Chem. Theory Comput. 2010, 6, 66-80
33. Riley, K. E.; Hobza, P. Noncovalent Interactions in Biochemistry Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2011, 1, 3-17
34. Sponer, J.; Riley, K. E.; Hobza, P. Nature and Magnitude of Aromatic Stacking of Nucleic Acid Bases Phys. Chem. Chem. Phys. 2008, 10, 2595-2610
35. Sedlak, R.; Jurecka, P.; Hobza, P. Density Functional Theory-Symmetry Adapted Perturbation Treatment Energy Decomposition of Nucleic Acid Base Pairs Taken from DNA Crystal Geometry J. Chem. Phys. 2007, 127, 075104-075106
36. 60 Fullerene with a Rare Gas Atom Phys. Chem. Chem. Phys. 2011, 13, 732-743
37. Karthikeyan, S.; Sedlak, R.; Hobza, P. On the Nature of Stabilization in Weak, Medium, and Strong Charge-Transfer Complexes: CCSD(T)/CBS and SAPT Calculations J. Phys. Chem. A 2011, 115, 9422-9428
38. Sedlak, R.; Hobza, P.; Patwari, G. N. Hydrogen-Bonded Complexes of Phenylacetylene with Water, Methanol, Ammonia, and Methylamine. The Origin of Methyl Group-Induced Hydrogen Bond Switching J. Phys. Chem. A 2009, 113, 6620-6625
39. Munusamy, E.; Sedlak, R.; Hobza, P. On the Nature of the Stabilization of Benzene···Dihalogen and Benzene··· Dinitrogen Complexes: CCSD(T)/CBS and DFT-SAPT Calculations ChemPhysChem 2011, 12, 3253-3261
40. Peterson, K. A.; Figgen, D.; Goll, E.; Stoll, H.; Dolg, M. Systematically Convergent Basis Sets with Relativistic Pseudopotentials. II. Small-core Pseudopotentials and Correlation Consistent Basis Sets for the Post- d Group 16-18 Elements J. Chem. Phys. 2003, 119, 11113-11123
41. Peterson, K. A. Systematically Convergent Basis Sets With Relativistic Pseudopotentials. I. Correlation Consistent Basis Sets for the Post- d Group 13-15 Elements J. Chem. Phys. 2003, 119, 11099-11112
42. Halkier, A.; Helgaker, T.; Jorgensen, P.; Klopper, W.; Olsen, J. Basis-set Convergence of the Energy in Molecular Hartree-Fock Calculations Chem. Phys. Lett. 1999, 302, 437-446 (Pubitemid 129593885)
43. 2O Chem. Phys. Lett. 1998, 286, 243-252 (Pubitemid 128181147)
44. 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
45. Hobza, P.; Sponer, J. Toward True DNA Base-Stacking Energies: MP2, CCSD(T), and Complete Basis Set Calculations J. Am. Chem. Soc. 2002, 124, 11802-11808
46. Jurecka, P.; Hobza, P. On the Convergence of the (Delta-E CCSD(T)-Delta-E-MP2) Term for Complexes with Multiple H-bonds Chem. Phys. Lett. 2002, 365, 89-94
47. Dabkowska, I.; Jurecka, P.; Hobza, P. On Geometries of Stacked and H-bonded Nucleic Acid Base Pairs Determined at Various DFT, MP2 and CCSD(T) Levels up to the CCSD(T)/Complete Basis Set Limit Level J. Chem. Phys. 2005, 122, 204322-204329
48. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-class Functionals and 12 Other Functionals Theor. Chem. Acc. 2008, 120, 215-241
49. Kozuch, S.; Martin, J. M. L. Halogen Bonds: Benchmarks and Theoretical Analysis J. Chem. Theory Comput. 2013, 9, 1918-1931
50. 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, 154104-154123
51. Grimme, S.; Ehrlich, S.; Goerigk, L. Effect of the Damping Function in Dispersion Corrected Density Functional Theory J. Comput. Chem. 2011, 32, 1456-1465
52. 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 (Pubitemid 124000190)
53. 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 (Pubitemid 32138501)
54. Hesselmann, A.; Jansen, G. First-order Intermolecular Interaction Energies from Kohn-Sham Orbitals Chem. Phys. Lett. 2002, 357, 464-470
55. Hesselmann, A.; Jansen, G. Intermolecular Induction and Exchange-induction Energies from Coupled-perturbed Kohn-Sham Density Functional Theory Chem. Phys. Lett. 2002, 362, 319-325
56. Hesselmann, A.; Jansen, G. Intermolecular Dispersion Energies from Time-dependent Density Functional Theory Chem. Phys. Lett. 2003, 367, 778-784
57. 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
58. 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, 014103-014119
59. Jansen, G.; Hesselmann, A. Comment on: Using Kohn-Sham Orbitals in Symmetry-Adapted Perturbation Theory to Investigate Intermolecular Interactions J. Phys. Chem. A 2001, 105, 11156-11157
60. Misquitta, A. J.; Szalewicz, K. Intermolecular Forces from Asymptotically Corrected Density Functional Description of Monomers Chem. Phys. Lett. 2002, 357, 301-306
61. Stone, A. J. Distributed Multipole Analysis, or How to Describe a Molecular Charge Distribution Chem. Phys. Lett. 1981, 83, 233-239
62. Stone, A. J.; Alderton, M. Distributed Multipole Analysis Methods and Applications Mol. Phys. 1985, 56, 1047-1064
63. Stone, A. J. Distributed Multipole Analysis: Stability for Large Basis Sets J. Chem. Theory Comput. 2005, 1, 1128-1132
64. Stone, A. J. GDMA: Distributed Multipoles from Gaussian 98 Wavefunctions, version 2.2.04; Tech. Rep., University of Cambridge, 1998.
65. Stone, A. J.; Dullweber, A.; Engkvist, O.; Fraschini, E.; Hodges, M. P.; Meredith, A. W.; Nutt, D. R.; Popelier, P. L. A.; Wales, D. J. Orient: A Program for Studying Interactions Between Molecules, version 4.6.16; University of Cambridge, Cabmridge, U.K., 2002; Enquiries to Stone, A. J. ajs1@cam.ac.uk.
66. Werner, H.-J.; Knowles, P. J.; Manby, F. R.; Schütz, M.; Celani, P.; Knizia, G.; Korona, T.; Lindh, R.; Mitrushenkov, A.; Rauhut, G.; MOLPRO, A Package of ab initio Programs, version 2010.1; 2010; http://www.molpro.net.
67. TURBOMOLE V6.3 2011, A Development of the University of Karlsruhe and the Forschungszentrum Karlsruhe GmbH, 1989-2007; TURBOMOLE GmbH, since 2007; available from http://www.turbomole.com.
68. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint Chem. Rev. 1988, 88, 899-926
69. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.
70. 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