Halogen bonding: Unifying perspectives on organic and inorganic cases

Journal of Physical Chemistry A

Volumn 118, Issue 43, 2014, Pages 10090-10100

  Tawfik, Marina ^a   Donald, Kelling J ^a  

^a UNIVERSITY OF RICHMOND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGEN BONDING;

EID: 84908577547     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp507879w     Document Type: Article

References (43)

1. See Odd Hassel's 1969 Nobel lecture for examples of apparently halogen-bonded complexes that were identified in that context as charge-transfer complexes: "Structural Aspects of Interatomic Charge-Transfer Bonding". Available free of cost at http://www.nobelprize.org/nobel-prizes/chemistry/laureates/1969/hassel-lecture.pdf. Nobel Media AB 2014. Retrieved July 30, 2014. The lecture is also available elsewhere (see ref 2).
2. Hassel, O. Structural Aspects of Interatomic Charge-Transfer Bonding Science 1970, 170, 497-502
3. Legon, A. C. The Halogen Bond: an Interim Perspective Phys. Chem. Chem. Phys. 2010, 12, 7736-7747
4. Palusiak, M. On the Nature of Halogen Bond-The Kohn-Sham Molecular Orbital Approach J. Mol. Struct.: THEOCHEM 2010, 945, 89-92
5. Stone, A. J. Are Halogen Bonded Structures Electrostatically Driven? J. Am. Chem. Soc. 2013, 135, 7005-7009
6. Wang, C.; Danovich, D.; Mo, Y.; Shaik, S. On The Nature of the Halogen Bond J. Chem. Theory Comput. 2014, 10, 3726-3737
7. 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
8. Murray, J. S.; Paulsen, K.; Politzer, P. Molecular Surface Electrostatic Potentials in the Analysis of Non-Hydrogen-Bonding Noncovalent Interactions Proc. Indian Acad. Sci. (Chem. Sci.) 1994, 106, 267-275
9. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P. Halogen bonding: the σ-hole (Proceedings of "Modeling interactions in biomolecules II", Prague, September 5th-9th, 2005) J. Mol. Model. 2007, 13, 291-296
10. Emsley, J. The Elements, 3 rd ed.; Oxford Univ. Press: Oxford, 1998.
11. Kutzelnigg, W. Chemical Bonding in Higher Main Group Elements Angew. Chem., Int. Ed. Engl. 1984, 23, 272-295
12. Politzer, P.; Harris, R. R. Properties of Atoms in Molecules. I. Proposed Definition of the Charge on an Atom in a Molecule J. Am. Chem. Soc. 1970, 92, 6451-6454
13. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. An Overview of Halogen Bonding J. Mol. Model 2007, 13, 305-311
14. Politzer, P.; Murray, J. S. Halogen Bonding: an Interim Discussion ChemPhysChem 2013, 14, 278-294
15. Auffinger, P.; Hays, F. A.; Westhof, E.; Shing-Ho, P. Halogen Bonds in Biological Molecules Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789-16794
16. De Moliner, E.; Brown, N. R.; Johnson, L. N. Alternative Binding Modes of an Inhibitor to two Different Kinases Eur. J. Biochem. 2003, 270, 3174-3181
17. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Halogen Bonding Based Recognition Processes: A World Parallel to Hydrogen Bonding Acc. Chem. Res. 2005, 38, 386-395
18. Metrangolo, P.; Pilati, T.; Resnati, G.; Stevenazzi, A. Halogen Bonding Driven Self-Assembly of Fluorocarbons and Hydrocarbons Curr. Opin. Colloid Interface Sci. 2003, 8, 215-222
19. Donald, K.; Wittmaack, B. K.; Crigger, C. Tuning Sigma-Holes: Charge Redistribution in the Heavy (Group 14) Analogues of Simple and Mixed Halomethanes can Impose Strong Propensities for Halogen Bonding J. Phys. Chem. A 2010, 114, 7213-7222
20. Head-Gordon, M.; Head-Gordon, T. Analytic MP2 Frequencies without Fifth-Order Storage. Theory and Application to Bifurcated Hydrogen Bonds in the Water Hexamer Chem. Phys. Lett. 1994, 220, 122-128 and references therein
21. 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
22. The Stuttgart/Cologne correlation consistent triple-zeta (cc-pVTZpp) basis sets used are from the website: http://www.tc.uni-koeln.de/PP/clickpse.en.html.
23. 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 (for Sn and Pb)
24. Peterson, K. A.; Shepler, B. C.; Figgen, D.; Stoll, H. On the Spectroscopic and Thermochemical Properties of ClO, BrO, IO, and Their Anions J. Phys. Chem. A 2006, 110, 13877-13883 (for I)
25. 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 A.1; Gaussian, Inc.: Wallingford, CT, 2009.
26. For a description of this procedure, see: Jensen, F. Introduction to Computational Chemistry; Wiley: New York, 1999; pp 172-173.
27. The ChemCraft graphical program: http://www.chemcraftprog.com (last accessed August 1, 2014).
28. See: Kemsley, J. Defining A New Carbon Bond Chem. Eng. News 2014, 92, 25-26
29. Mani, D.; Arunan, E. The X-CY (X = O/F, Y = O/S/F/Cl/Br/N/P) 'Carbon Bond' and Hydrophobic Interactions Phys. Chem. Chem. Phys. 2013, 15, 14377-14383
30. Bauá, A.; Mooibroek, T. J.; Frontera, A. Tetrel-Bonding Interaction: Rediscovered Supramolecular Force? Angew. Chem., Int. Ed. 2013, 52, 12317-12321
31. Thomas, S. P.; Pavan, M. S.; Guru Row, T. N. Experimental Evidence for 'Carbon Bonding' in the Solid State from Charge Density Analysis Chem. Commun. 2014, 50, 49-51
32. N2 Reaction Phys. Chem. Chem. Phys. 2014, 16, 1824-1834
33. Politzer, P.; Murray, J.; Clark, T. Halogen Bonding and Other σ-Hole Interactions: a Perspective Phys. Chem. Chem. Phys. 2013, 15, 11178-11189
34. 4·Base Complexes J. Phys. Chem. A 2013, 117, 14176-14183
35. Wang, Z.-X.; Zhang, J.-C.; Wu, J.-Y.; Cao, W.-L. Theoretical Study on Intermolecular Interactions between Furan and Dihalogen Molecules XY (X, Y = F, Cl, Br) J. Chem. Phys. 2007, 126, 134301-1-134301-7
36. Cooke, S. A.; Corlett, G. K.; Holloway, J. H.; Legon, A. C. Evidence Concerning the Relative Nucleophilicities of Non-Bonding and π-Bonding Electrons in Furan from the Rotational Spectrum of Furan⋯ClF J. Chem. Soc., Faraday Trans. 1998, 94, 2675-2680 See also related studies of interactions between ethene and terminal halide centers by the same research group (refs 42 and 43)
37. 2 Characterized By Its Rotational Spectrum Phys. Chem. Chem. Phys. 2001, 3, 1397-14202
38. 3 Identified by Broadband Rotational Spectroscopy J. Mol. Spectrosc. 2012, 280, 47-53
39. Wang, Z.; Zheng, B.; Yu, X.; Li, X.; Yi, P. Structure, Properties, And Nature Of The Pyridine-XY (X, Y = F, Cl, Br) Complexes: An Ab Initio Study J. Chem. Phys. 2010, 132, 164104-1-164104-5
40. Murray, J. S.; Lane, P.; Politzer, P. Expansion of the σ-hole Concept J. Mol. Model. 2009, 15, 723-729
41. 4 with Amines Int. J. Quantum Chem. 2009, 109, 3773-3780
42. Caminati, W.; Maris, A.; Dell'Erba, A.; Favero, P. G. Dynamical Behavior and Dipole-Dipole Interactions of Tetrafluoromethane-Water Angew. Chem., Int. Ed. 2006, 45, 6711-6714
43. Pauling, L. The Dependence of Bond Energy on Bond Length J. Phys. Chem. 1954, 58, 662-666