On the physical nature of halogen bonds: A QTAIM study

Journal of Physical Chemistry A

Volumn 117, Issue 36, 2013, Pages 8969-8980

  Syzgantseva, Olga A ^a   Tognetti, Vincent ^a   Joubert, Laurent ^a  

^a NORMANDIE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS-IN-MOLECULES; BOND CRITICAL POINTS; DESCRIPTORS; HALOGEN BONDS; LEWIS BASIS; PHYSICAL NATURE; QUANTUM ATOMS; SECONDARY INTERACTIONS;

BINDING ENERGY; HALOGEN COMPOUNDS; QUANTUM THEORY;

COMPLEXATION;

HALOGEN;

CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; CONFORMATION; ELECTRON TRANSPORT; PHYSICAL PHENOMENA; QUANTUM THEORY; STATIC ELECTRICITY;

ELECTRON TRANSPORT; HALOGENS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHYSICAL PROCESSES; QUANTUM THEORY; STATIC ELECTRICITY;

EID: 84884315985     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp4059774     Document Type: Conference Paper

References (126)

1. Metrangolo, P., Resnati, G., Eds. Halogen Bonding: Fundamentals and Applications, Structure and Bonding; Structure and Bonding, No. 126; Springer: Berlin, 2008.
2. Metrangolo, P.; Pilati, R.; Resnati, G. Halogen Bonding and Other Noncovalent Interactions Involving Halogens: A Terminology Issue CrystEngComm 2006, 8, 946-947
3. Metrangolo, P.; Resnati, G. Halogen Bonding: Where We Are and Where We Are Going Cryst. Growth Des. 2012, 12, 5835-5838
4. Legon, A. C. The Halogen Bond: An Interim Perspective Phys. Chem. Chem. Phys. 2010, 12, 7736-7747
5. Fourmigué, M. Halogen Bonding: Recent Advances Curr. Opin. Solid State Mater. Sci 2009, 13, 36-45
6. Parisini, E.; Metrangolo, P.; Pilati, T.; Resnati, G.; Terraneo, G. Halogen Bonding in Halocarbon-Protein Complexes: A Structural Survey Chem. Soc. Rev. 2011, 40, 2267-2278
7. Lu, Y.; Wang, Y.; Zhu, W. Nonbonding Interactions of Organic Halogens in Biological Systems: Implications for Drug Discovery and Biomolecular Design Phys. Chem. Chem. Phys. 2010, 12, 4543-4551
8. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, S. Halogen Bonds in Biological Molecules Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789-167945
9. Hardegger, L.-A.; Kuhn, B.; Spinnler, B.; Anselm, L.; Ecabert, R.; Stihle, M.; Gsell, B.; Thoma, R.; Diez, J.; Benz, J.; Plancher, J.-M.; Hartmann, G.; Banner, D. W.; Haap, W.; Diederich, F. Systematic Investigation of Halogen Bonding in Protein-Ligand Interactions Angew. Chem., Int. Ed. 2011, 50, 314-318
10. Jentzsch, A. V.; Matile, S. Transmembrane Halogen-Bonding Cascades J. Am. Chem. Soc. 2013, 135, 5302-5303
11. Wilcken, R.; Zimmermann, M. O.; Lange, A.; Joerger, A. C.; Boeckler, F. M. Principles and Applications of Halogen Bonding in Medicinal Chemistry and Chemical Biology J. Med. Chem. 2013, 56, 1363-1388
12. Meyer, F.; Dubois, P. Halogen Bonding at Work: Recent Applications in Synthetic Chemistry and Materials Science CrystEngComm 2013, 15, 3058-3071
13. Lu, Y.; Shi, T.; Wang, Y.; Yang, H.; Yan, X.; Luo, X.; Jiang, H.; Zhu, W. Halogen Bonding-A Novel Interaction for Rational Drug Design? J. Med. Chem. 2009, 52, 2854-2862
14. Metrangolo, P.; Resnati, G.; Pilati, T.; Biella, S. Halogen Bonding in Crystal Engineering Struct. Bonding (Berlin) 2008, 126, 105-136
15. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Halogen Bonding in Supramolecular Chemistry Angew. Chem., Int. Ed. 2008, 47, 6114-6127
16. Metrangolo, P.; Resnati, G. Halogen Bonding: A Paradigm in Supramolecular Chemistry Chem.-Eur. J. 2001, 7, 2511-2519
17. Voth, A. R.; Hays, F. A.; Ho, P. S. Directing Macromolecular Conformation through Halogen Bonds Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 6188-6193
18. Vidal, F.; Dávila, M. A.; Torcuato, A. S.; Gómez-Sal, P.; Mosquera, M. E. Functionalized Imido-Bridged Ti(IV) Complexes As New Building Blocks for Supramolecular Arrangements: Generation of a 1D Structure through a Mg-Cl⋯I-C Halogen Bonding Interaction Dalton Trans. 2013, 42, 7074-7084
19. Metrangolo, P.; Resnati, G.; Pilati, T.; Biella, S. In Halogen Bonding: Fundamentals and Applications: Metrangolo, P.; Resnati, G., Eds.; Springer: Berlin, 2008; pp 105-136.
20. Abate, A.; Biella, S.; Cavallo, G.; Meyer, F.; Neukirch, H.; Metrangolo, P.; Pilati, T.; Resnati, G.; Terraneo, G. Halide Anions Driven Self-Assembly of Haloperfluoroarenes: Formation of One-Dimensional Non-Covalent Copolymers J. Fluorine Chem. 2009, 130, 1171-1177
21. Minguez Espallargas, G.; Zordan, F.; Arroyo Marin, L.; Adams, H.; Shankland, K.; van de Streek, J.; Brammer, L. Rational Modification of the Hierarchy of Intermolecular Interactions in Molecular Crystal Structures by Using Tunable Halogen Bonds Chem.-Eur. J. 2009, 15, 7554-7568
22. Nguyen, H. L.; Horton, P. N.; Hursthouse, M. B.; Legon, A. C.; Bruce, D. W. Halogen Bonding: A New Interaction for Liquid Crystal Formation J. Am. Chem. Soc. 2004, 126, 16-17
23. Lauher, J. W.; Fowler, F. W.; Goroff, N. S. Single-Crystal-to-Single- Crystal Topochemical Polymerizations by Design Acc. Chem. Res. 2008, 41, 1215-1229
24. Goroff, N. S.; Luo, L.; Wilhelm, C.; Sun, A.; Webb, J. A. Halogen-Bond-Driven Assembly of Polyynes for Topochemical Polymerization. Abstracts of Papers; 238th ACS National Meeting, Washington, DC, United States, August 16-20, 2009.
25. Benesi, H. A.; Hildebrand, J. H. Ultraviolet Absorption Bands of Iodine in Aromatic Hydrocarbons J. Am. Chem. Soc. 1948, 70, 2832-2833
26. Novick, S. E.; Janda, K. C.; Klemperer, W. HFClF: Structure and Bonding J. Chem. Phys. 1976, 65, 5115-5121
27. 3 Probed by Broadband Rotational Spectroscopy Phys. Chem. Chem. Phys. 2011, 13, 20736-20744
28. 3 Identified by Broadband Rotational Spectroscopy J. Mol. Spectrosc. 2012, 280, 47-53
29. Weingarth, M.; Raouafi, N.; Jouvelet, B.; Duma, L.; Bodenhausen, G.; Boujlel, K.; Scöllhorn, B.; Tekley, P. Revealing Molecular Self-Assembly and Geometry of Non-Covalent Halogen Bonding by Solid-State NMR Spectroscopy Chem. Commun. 2008, 45, 5981-5983
30. Chudzinski, M. G.; McClary, C. A.; Taylor, M. S. Anion Receptors Composed of Hydrogen- and Halogen-Bond Donor Groups: Modulating Selectivity with Combinations of Distinct Noncovalent Interactions J. Am. Chem. Soc. 2011, 133, 10559-10567
31. Hauchecorne, D.; Szostak, R.; Herrebout, W. A.; van der Vekken, B. J. CX⋯O Halogen Bonding: Interactions of Trifluoromethyl Halides with Dimethyl Ether ChemPhysChem 2009, 10, 2105-2115
32. Cappelletti, D.; Candori, P.; Pirano, F.; Belpassi, L.; Tarantelli, F. Nature and Stability of Weak Halogen Bonds in the Gas Phase: Molecular Beam Scattering Experiments and ab Initio Charge Displacement Calculations Cryst. Growth Des. 2011, 11, 4279-4283
33. Hassel, O.; Hvoslef, J. The Structure of Bromine 1,4-Dioxanate Acta Chem. Scand. 1954, 8, 873
34. Desiraju, G. R.; Ho, P. S.; Kloo, L.; Legon, A. C.; Marquardt, R.; Metrangolo, P.; Politzer, P.; Resnati, G.; Rissanen, K. Definition of the Halogen Bond. Chem. Int. 2012, 34, http://media.iupac.org/reports/provisional/ abstract12/metrangolo-prs.pdf.
35. Politzer, P.; Murray, J. S.; Clark, T. Halogen Bonding: An Electrostatically-Driven Highly Directional Noncovalent Interaction Phys. Chem. Chem. Phys. 2010, 12, 7748-7757
36. Carter, M.; Shing, Ho, P. Assaying the Energies of Biological Halogen Bonds Cryst. Growth Des. 2011, 11, 5087-5095
37. 19F NMR Study of C-I⋯π Halogen Bonding Chem. Phys. 2011, 381, 5-10
38. Gushchin, P. V.; Kuznetsov, M. L.; Haukka, M.; Kukushkin, V. Y. Recognition of a Novel Type X = N-Hal⋯Hal (X = C, S, P; Hal = F, Cl, Br, I) Halogen Bonding J. Phys. Chem. A 2013, 117, 2827-2834
39. Johansson, M. P.; Swart, M. Intramolecular Halogen-Halogen Bonds Phys. Chem. Chem. Phys. 2013, 15, 11543-11553
40. Wang, W.; Ji, B.; Zhang, Y. Chalcogen Bond: A Sister Noncovalent Bond to Halogen Bond J. Phys. Chem. A 2009, 113, 8132-8135
41. Scheiner, S. The Pnicogen Bond: its Relation to Hydrogen, Halogen, and Other Noncovalent Bonds Acc. Chem. Res. 2013, 46, 280-288
42. Bauzá, B.; Quiñonero, D.; Deyá, P. M.; Fontrera, A. Halogen Bonding versus Chalcogen and Pnicogen Bonding: A Combined Cambridge Structural Database and Theoretical Study CrystEngComm 2013, 15, 3137-3144
43. Scheiner, S. Sensitivity of Noncovalent Bonds to Intermolecular Separation: Hydrogen, Halogen, Chalcogen, and Pnicogen Bonds CrystEngComm 2013, 15, 3119-3124
44. McAllister, L. J.; Bruce, D. W.; Karadakov, P. B. Quantum Chemical Investigation of Attractive Non-Covalent Interactions Between Halomethanes and Rare Gases J. Phys. Chem. A 2012, 116, 10621-10628
45. Riley, K. E.; Hobza, P. Strength and Character of Halogen Bonds in Protein-Ligand Complexes Cryst. Growth Des. 2011, 11, 4272-4278
46. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. An Overview of Halogen Bonding J. Mol. Model. 2007, 13, 305-311
47. Politzer, P.; Riley, K. E.; Bulat, F. A.; Murray, J. S. Perspectives on Halogen Bonding and Other σ-Hole Interactions: lex parsimoniae (Occam's Razor) Comput. Theor. Chem. 2012, 998, 2-8
48. Politzer, P.; Murray, J. S. Halogen Bonding: An Interim Discussion ChemPhysChem 2013, 14, 278-294
49. 2 Theor. Chem. Acc. 2012, 131, 1114
50. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. Halogen Bonding: The Sigma-Hole J. Mol. Model. 2007, 13, 291-296
51. Brinck, T.; Murray, J. S.; Politzer, P. Surface Electrostatic Potentials of Halogenated Methanes As Indicators of Directional Intermolecular Interactions Int. J. Quantum Chem. 1992, 44, 57-64
52. Murray, J. S.; Lane, P.; Politzer, P. Expansion of the Sigma-Hole Concept J. Mol. Model. 2009, 15, 723-729
53. Murray, J. S.; Lane, P.; Clark, T.; Politzer, P. σ-Hole Bonding: Molecules Containing Group VI atoms J. Mol. Model. 2007, 13, 1033-1038
54. Hennemann, M.; Murray, J. S; Riley, K. E.; Politzer, P.; Clark, T. Polarization-Induced σ-Holes and Hydrogen Bonding J. Mol. Model. 2012, 18, 2461-2469
55. Clark, T. σ-Holes WIRES Comp. Mol. Sci. 2013, 3, 13-20
56. Amezaga, N. J. M.; Pamies, S. C.; Peruchena, N. M.; Sosa, G. L. Halogen Bonding: A Study Based on the Electronic Charge Density J. Phys. Chem. A 2010, 114, 552-562
57. Zhang, X.; Zeng, Y.; Li, X.; Meng, L.; Zheng, S. A Computational Study on the Nature of the Halogen Bond between Sulfides and Dihalogen Molecules Struct. Chem. 2011, 22, 567-576
58. 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 Analyses Comput. Theor. Chem 2012, 998, 164-172
59. Eskanderi, K.; Zariny, H. Halogen Bonding: A Lump-Hole Interaction Chem. Phys. Lett. 2010, 492, 9-13
60. Grabowski, S. J. Halogen Bond and Its Counterparts: Bent's Rule Explains the Formation of Nonbonding Interactions J. Phys Chem. A 2011, 115, 12340-12347
61. Grabowski, S. J. Hydrogen and Halogen Bonds Are Ruled by the Same Mechanisms Phys. Chem. Chem. Phys. 2013, 15, 7249-7259
62. Grabowski, S. J. Non-Covalent Interactions-QTAIM and NBO Analysis J. Mol. Model. 2012, 10.1007/s00894-012-1463-7
63. Wang, W.; Hobza, P. Origin of the X-Hal (Hal = Cl, Br) Bond-Length Change in the Halogen-Bonded Complexes J. Phys. Chem. A 2008, 112, 4114-4119
64. Wang, W.; Zhang, Y.; Ji, B. On the Difference of the Properties between the Blue-Shifting Halogen Bond and the Blue-Shifting Hydrogen Bond J. Phys. Chem. A 2010, 114, 7257-7260
65. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; The International Series of Monographs on Chemistry: No. 22; Oxford University Press: New York, 1990.
66. Popelier, P. L. Atoms in Molecules: An Introduction; Pearson Education: Harlow, U.K., 2000.
67. Alkorta, I.; Rozas, I.; Elguero, J. Charge-Transfer Complexes between Dihalogen Compounds and Electron Donor J. Phys. Chem. A 1998, 102, 9278-9285
68. Lu, Y.-X.; Zou, J.-W.; Wang, Y.-H.; Jiang, Y.-J.; Yu, Q.-S. Ab Initio Investigation of the Complexes between Bromobenzene and Several Electron Donors: Some Insights into the Magnitude and Nature of Halogen Bonding Interactions J. Phys. Chem. A 2007, 111, 10781-10788
69. Grabowski, S. J. QTAIM Characteristics of Halogen Bond and Related Interactions J. Phys. Chem. A 2012, 116, 1838-1845
70. Forni, A. Experimental and Theoretical Study of the Br⋯N Halogen Bond in Complexes of 1,4-Dibromotetrafluorobenzene with Dipyridyl Derivatives J. Phys. Chem. A 2009, 113, 3403-3412
71. Wang, W. Halogen Bond Involving Hypervalent Halogen: CSD Search and Theoretical Study J. Phys. Chem. A 2011, 115, 9294-9299
72. Mitoraj, M. P.; Michalak, A. Theoretical Description of Halogen Bonding-An Insight Based on the Natural Orbitals for Chemical Valence Combined with the Extended-Transition-State Method (ETS-NOCV). J. Mol. Model. DOI: 10.1007/s00894-012-1474-4. Open Access. 2012.
73. Dyduch, K.; Mitoraj, M. P.; Michalak, A. ETS-NOCV Description of σ-Hole Binding J. Mol. Model. 2013, 19, 2747-2758
74. Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. The Nature and Geometry of Intermolecular Interactions between Halogens and Oxygen or Nitrogen J. Am. Chem. Soc. 1996, 118, 3108-3116
75. Domagała, M.; Matczak, P.; Palusiak, M. Halogen Bond, Hydrogen Bond and N⋯C Interaction-On Interrelation among These Three Noncovalent Interactions Comput. Theor. Chem. 2012, 998, 26-33
76. Palusiak, M. On the Nature of Halogen Bond-The Kohn-Sham Molecular Orbital Approach J. Mol. Struct. (THEOCHEM) 2010, 945, 89-92
77. Xu, L.; Lv, J.; Sang, P.; Zou, J.-W.; Yu, Q.-S.; Xu, M.-B. Comparative Insight into the Halogen Bonding of 4-Chloropyridine and its Metal [CuI, ZnII] Coordinations with Halide Ions: A Theoretical Study on M-C-X⋯X′ Chem. Phys. 2011, 379, 66-72
78. Riley, K. E.; Hobza, P. Investigations into the Nature of Halogen Bonding Including Symmetry Adapted Perturbation Theory Analyses J. Chem. Theory Comput. 2008, 4, 232-242
79. Wang, Z.; Liu, Z.; Ding, X.; Yu, X.; Hou, B.; Yi, P. Comparisons of the Halogen-Bonded and Hydrogen-Bonded Complexes of Furan, Thiophene and Pyridine with Lewis Acids (ClF, HCl) Comput. Theor. Chem. 2012, 981, 1-6
80. 3I. Structural and Energy Analysis Including Relativistic Zero-Order Regular Approximation Approach in a Density Functional Theory Framework J. Phys. Chem. A 2002, 106, 9114-9119
81. Pinter, B.; Nagels, N.; Herrebout, W. A.; De Proft, F. Halogen Bonding from a Hard and Soft Acids and Bases Perspective: Investigation by Using Density Functional Theory Reactivity Indices Chem.-Eur. J. 2013, 19, 519-530
82. Pendás, A. M.; Blanco, M. A.; Francisco, E. Two-Electron Integrations in the Quantum Theory of Atoms in Molecules J. Chem. Phys. 2004, 120, 4581
83. Blanco, M. A.; Pendás, A. M.; Francisco, E. Interacting Quantum Atoms: A Correlated Energy Decomposition Scheme Based on the Quantum Theory of Atoms in Molecules J. Chem. Theory Comput. 2005, 1, 1096-1109
84. Pendás, A. M.; Blanco, M. A.; Francisco, E. A Molecular Energy Decomposition Scheme for Atoms in Molecules J. Chem. Theory Comput. 2006, 2, 90-102
85. Tiana, D.; Francisco, E.; Blanco, M. A.; Macchi, P.; Sironi, A.; Pendás, A. M. Bonding in Classical and Nonclassical Transition Metal Carbonyls: The Interacting Quantum Atoms Perspective J. Chem. Theory Comput. 2010, 6, 1064-1074
86. Pendás, A. M.; Blanco, M. A.; Francisco, E. The Nature of the Hydrogen Bond: A Synthesis from the Interacting Quantum Atoms Picture J. Chem. Phys. 2006, 125, 184112
87. Tognetti, V.; Joubert, L. On the Physical Role of Exchange in the Formation of an Intramolecular Bond Path between two Electronegative Atoms J. Chem. Phys. 2013, 138, 024102
88. Karpfen, A. The Intermolecular Interaction in the Charge-Tranfer Complexes between Amines and Halogens: A Theoretical Characterization of the Trends in Halogen Bonding Theor. Chem. Acc. 2003, 110, 1-9
89. Karpfen, A.; Kryachko, E. S. On Blue Shifts of C-H Stretching Modes of Dimethyl Ether in Hydrogen- and Halogen-Bonded Complexes Chem. Phys. Lett. 2006, 431, 428-433
90. 3: Towards Understanding the Nature of Halogen Bonding and the Electron-Accepting Propensities of Covalently Bonded Halogen Atoms Chem.-Eur. J. 2005, 11, 740-751
91. Lu, Y.-X.; Zou, J.-W.; Wang, Y.-H.; Yu, Q.-S. Ab Initio and Atoms in Molecules: Analyses of Halogen Bonding with a Continuum of Strength J. Mol. Struct. (THEOCHEM) 2006, 776, 83-87
92. Wang, Y.-H.; Zou, J.-W.; Lu, Y.-X.; Yu, Q.-S.; Xu, H.-Y. Single-Electron Halogen Bond: Ab Initio Study Int. J. Quantum Chem. 2007, 107, 501-506
93. Lu, Y.-X.; Zou, J.-W.; Fan, J.-C.; Zhao, W.-N.; Jiang, Y.-J.; Yu, Q.-S. Ab Initio Calculations on Halogen-Bonded Complexes and Comparison with Density Functional Methods J. Comput. Chem. 2009, 30, 725-732
94. Li, Q.-Z.; Dong, X.; Jing, B.; Li, W.-Z.; Cheng, J.-B.; Gong, B.-A.; Yu, Z.-W. A New Unconventional Halogen Bond C-X⋯H-M between HCCX (X = Cl and Br) and HMH (M = Be and Mg): An Ab Initio Study J. Comput. Chem. 2010, 31, 1662-1669
95. Ramasami, P.; Ford, T. A. Ab Initio Studies of the Properties of Some Halogen-Bonded Complexes of Ammonia, Water, Phosphine and Hydrogen Sulphide Comput. Theor. Chem. 2012, 990, 227-235
96. Tsuzuki, S.; Uchimaru, T.; Wakisaka, A.; Ono, T.; Sonoda, T. CCSD(T) Level Interaction Energy for Halogen Bond between Pyridine and Substituted Iodobenzenes: Origin and Additivity of Substituent Effects Phys. Chem. Chem. Phys. 2013, 15, 6088-6096
97. Karpfen, A. Theoretical Characterization of the Trends in Halogen Bonding Struct. Bonding (Berlin) 2008, 126, 1-15
98. Politzer, P.; Murray, J. S.; Concha, M. C. Halogen Bonding and the Design of New Materials: Organic Bromides, Chlorides and Perhaps even Fluorides as Donors J. Mol. Model. 2007, 13, 643-650
99. Metrangolo, P.; Murray, J. S.; Pilati, T.; Politzer, P.; Resnati, G.; Terraneo, G. The Fluorine Atom as a Halogen Bond Donor, viz. a Positive Site CrystEngComm 2011, 13, 6593-6596
100. Lipkowski, P.; Grabowski, S. J.; Leszszynski, J. Properties of the Halogen-Hydride Interaction: An ab Initio and "Atoms in Molecules" Analysis J. Phys. Chem. A 2006, 110, 10296-10302
101. Chai, J.-D.; Head-Gordon, M. Long-Range Corrected Hybrid Density Functionals with Damped Atom-Atom Dispersion Corrections Phys. Chem. Chem. Phys. 2008, 10, 6615-6620
102. Grimme, S. Semiempirical GGA-type Density Functional Constructed with a Long-Range Dispersion Correction J. Comput. Chem. 2006, 27, 1787-1799
103. Frisch, M. J. Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford, CT, 2009.
104. 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
105. Kozuch, S.; Martin, J. M. L. Halogen Bonds: Benchmarks and Theoretical Analysis J. Chem. Theor. Comput. 2013, 9, 1918-1931
106. Bankiewicz, B.; Palusiak, M. The Shape of the Halogen Atom-Anisotropy of Electron Distribution and its Dependence on Basis Set and Method Used Struct. Bonding (Berlin) 2013, 24, 1297-1306
107. Politzer, P.; Murray, J. S. Enthalpy and Entropy Factors in Gas Phase Halogen Bonding: Compensation and Competition CrystEngComm 2013, 15, 3145-3150
108. Lu, Y.; Li, H.; Zhu, X.; Liu, H.; Zhu, W. Effects of Solvent on Weak Halogen Bonds: Density Functional Theory Calculations Int. J. Quantum Chem. 2012, 112, 1421-1430
109. Forni, A.; Rendine, S.; Pieraccini, S.; Sironi, M. Solvent Effect on Halogen Bonding: The Case of the I⋯O Interaction J. Mol. Graphics 2012, 38, 31-39
110. Keith, T. A. AIMAll, Version 12.09.23; TK Gristmill Software: Overland Park, KS, U.S.A., 2012, (aim.tkgristmill.com).
111. Cooper, V. R. Van der Waals Density Functional: An Appropriate Exchange Functional Phys. Rev. B 2010, 81, 161104
112. Grimme, S.; Schreiner, P. R. Steric Crowding can Stabilize a Labile Molecule: Solving the Hexaphenylethane Riddle Angew. Chem., Int. Ed. 2011, 50, 12639-12642
113. Fradera, X.; Austen, M. A.; Bader, R. F. W. The Lewis Model and Beyond J. Phys. Chem. A 1999, 103, 304-314
114. Fradera, X.; Poater, J.; Simon, S.; Duran, M.; Solá, M. Electron-Pairing Analysis from Localization and Delocalization Indices in the Framework of the Atoms-in-Molecules Theory Theor. Chem. Acc. 2002, 108, 214-224
115. Matito, E.; Solá, M.; Salvador, P.; Duran, M. Electron Sharing Indexes at the Correlated Level. Application to Aromaticity Calculations Faraday Discuss. 2007, 135, 325-345
116. Firme, C. L.; Antunes, O. A. C.; Esteves, P. M. Electronic Nature of Planar Cyclobutenyl Dication Derivatives J. Phys. Chem. A 2007, 111, 11904-11907
117. Ponder, J. W.; Case, D. A. Force Fields for Protein Simulations Adv. Protein Chem. 2003, 66, 27-85
118. Popelier, P. L. A. Quantum Chemical Topology: Knowledgeable Atoms in Peptides AIP Conf. Proc. 2012, 1456, 261-268
119. Jahromi, H. J.; Eskanderi, K. Halogen Bonding: A Theoretical Study Based on Atomic Multipoles Derived from Auantum Theory of Atoms in Molecules Struct. Chem. 2013, 24, 1281-1287
120. Rafat, M.; Popelier, P. L. A. Topological Atom-Atom Partitioning of Molecular Exchange Energy and Its Multipolar Convergence. In The Quantum Theory of Atoms in Molecules: From Solid State to DNA and Drug Design; Matta, C. F.; Russel, J., Eds.; Wiley-VCH Verlag GmbH & Co: Weinheim, Germany, 2007.
121. Popelier, P. L. A.; Joubert, L. The Elusive Atomic Rationale for DNA Base Pair Stability J. Am. Chem. Soc. 2002, 124, 8725-8729
122. Cremer, D.; Kraka, E. Chemical Bonds without Bonding Electron Density-Does the Difference Electron-Density Analysis Suffice for a Description of the Chemical Bond? Angew. Chem., Int. Ed. 1984, 23, 627-628
123. Bader, R. F. W.; Gatti, C. A Green's Function for the Density Chem. Phys. Lett. 1998, 287, 233-238
124. Gatti, C.; Cargnoni, F.; Bertini, L. Chemical Information from the Source Function J. Comput. Chem. 2003, 24, 422-436
125. Gatti, C.; Lasi, D. Source Function Description of Metal-Metal Bonding in d-Block Organometallic Compounds Faraday Discuss. 2007, 135, 55-78
126. Pendás, A. M.; Francisco, E.; Blanco, M. A.; Gatti, C. Bond Paths as Privileged Exchange Channels Chem.-Eur. J. 2007, 13, 9362-9371