The X-C⋯π (X = F, Cl, Br, CN) carbon bond

Journal of Physical Chemistry A

Volumn 118, Issue 43, 2014, Pages 10081-10089

  Mani, Devendra ^a,b   Arunan, Elangannan ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON BOND;

EID: 84908582582     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp507849g     Document Type: Article

References (44)

1. Hobza, P.; Müller-Dethlefs, K. Non-Covalent Interactions: Theory and Experiment; Royal Society Of Chemistry: Cambridge, U.K., 2010.
2. Wang, W.; Ji, B.; Zhang, Y. Chalcogen Bond: A Sister Noncovalent Bond to Halogen Bond J. Phys. Chem. A 2009, 113, 8132-8135
3. Scheiner, S. A New Noncovalent Force: Comparison of P⋯N Interaction with Hydrogen and Halogen Bonds J. Chem. Phys. 2011, 134, 094315-094319
4. Mani, D.; Arunan, E. The X-C⋯Y (X = O/F, Y = O/S/F/Cl/Br/N/P) 'Carbon Bond' and Hydrophobic Interactions Phys. Chem. Chem. Phys. 2013, 15, 14377-14383
5. Arunan, E.; Desiraju, G. R.; Klein, R. A.; Sadlej, J.; Scheiner, S.; Alkorta, I.; Clary, D. C.; Crabtree, R. H.; Dannenberg, J. J.; Hobza, P. Definition of the Hydrogen Bond (IUPAC Recommendations 2011) Pure Appl. Chem. 2011, 83, 1637-1641
6. Arunan, E.; Desiraju, G. R.; Klein, R. A.; Sadlej, J.; Scheiner, S.; Alkorta, I.; Clary, D. C.; Crabtree, R. H.; Dannenberg, J. J.; Hobza, P. Defining the Hydrogen Bond: An Account Pure Appl. Chem. 2011, 83, 1619-1636
7. 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 (IUPAC Recommendations 2013) Pure Appl. Chem. 2013, 85, 1711-1713
8. Scheiner, S. Effects of Substituents upon the P⋯N Noncovalent Interaction: The Limits of Its Strength J. Phys. Chem. A 2011, 115, 11202-11209
9. Scheiner, S. The Pnicogen Bond: Its Relation to Hydrogen, Halogen, and Other Noncovalent Bonds Acc. Chem. Res. 2013, 46, 280-288
10. Del Bene, J. E.; Alkorta, I.; Sánchez-Sanz, G.; Elguero, J. Interplay of F-H⋯F Hydrogen Bonds and P⋯N Pnicogen Bonds J. Phys. Chem. A 2012, 116, 9205-9213
11. Adhikari, U.; Scheiner, S. Effects of Charge and Substituent on the S⋯N Chalcogen Bond J. Phys. Chem. A 2014, 118, 3183-3192
12. Bauzá, A.; Quiñonero, D.; Deyà, P. M.; Frontera, A. Halogen Bonding versus Chalcogen and Pnicogen Bonding: A Combined Cambridge Structural Database and Theoretical Study CrystEngComm 2013, 15, 3137-3144
13. 2 to Molecules Containing a Carbonyl Group. The Dominating Role of the Chalcogen Bond J. Phys. Chem. A 2014, 118, 3835-3845
14. Thomas, S. P.; Pavan, M. S.; Row, T. G. Experimental Evidence for 'Carbon Bonding' in the Solid State from Charge Density Analysis Chem. Commun. (Cambridge, U.K.) 2014, 50, 49-51
15. N2 Reaction Phys. Chem. Chem. Phys. 2014, 16, 1824-1834
16. Li, Q.; Guo, X.; Yang, X.; Li, W.; Cheng, J.; Li, H.-B. A σ-Hole Interaction with Radical Species as Electron Donors: Does Single-Electron Tetrel Bonding Exist? Phys. Chem. Chem. Phys. 2014, 16, 11617-11625
17. 3-X, Should One Refer to Them As Carbon and Dicarbon Bonds! Phys. Chem. Chem. Phys. 2014, 16, 17238-17252
18. Bauzá, A.; Mooibroek, T. J.; Frontera, A. Tetrel-Bonding Interaction: Rediscovered Supramolecular Force? Angew. Chem. 2013, 125, 12543-12547
19. Mani, D.; Arunan, E. Microwave Spectroscopic and Atoms in Molecules Theoretical Investigations on the Ar⋯Propargyl Alcohol Complex: Ar⋯H-O, Ar⋯π, and Ar⋯C Interactions ChemPhysChem 2013, 14, 754-763
20. - (X, Y= Cl, Br) Complexes Chem. Phys. Lett. 2014, 598, 1-4
21. Li, Q.-Z.; Zhuo, H.; Li, H.-B.; Liu, Z.-B.; Li, W.-Z.; Cheng, J.-B. Tetrel-Hydride Interaction between XH3F (X = C, Si, Ge, Sn) and HM (M= Li, Na, Beh, Mgh) J. Phys. Chem. A 2014, 10.1021/jp503735u
22. Mani, D. Microwave Spectroscopic and Atoms in Molecules Theoretical Investigations on Weakly Bound Complexes: From Hydrogen Bond to 'Carbon Bond'; Ph.D. Dissertation, Indian Institute of Science, Bangalore, India, 2013.
23. Gutowsky, H. S.; Emilsson, T.; Arunan, E. Low- J Rotational Spectra, Internal Rotation, and Structures of Several Benzene-Water Dimers J. Chem. Phys. 1993, 99, 4883-4893
24. Nishio, M.; Hirota, M.; Umezawa, Y. The CH/π Interaction: Evidence, Nature, and Consequences; John Wiley & Sons: New York, 1998; Vol. 21.
25. Arunan, E.; Gutowsky, H. S. The Rotational Spectrum, Structure and Dynamics of a Benzene Dimer J. Chem. Phys. 1993, 98, 4294-4296
26. Arman, H. D.; Metrangolo, P.; Resnati, G. Halogen Bonding: Fundamentals and Applications; Springer: Berlin, 2008; Vol. 126.
27. Scheiner, S.; Adhikari, U. Abilities of Different Electron Donors (D) to Engage in a P⋯D Noncovalent Interaction J. Phys. Chem. A 2011, 115, 11101-11110
28. Alkorta, I.; Rozas, I.; Elguero, J. Molecular Complexes Between Silicon Derivatives and Electron-Rich Groups J. Phys. Chem. A 2001, 105, 743-749
29. Politzer, P.; Murray, J. S.; Clark, T. Halogen Bonding and Other σ-Hole Interactions: A Perspective Phys. Chem. Chem. Phys. 2013, 15, 11178-11189
30. 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.
31. 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
32. Keith Todd, A. AIMAll, version 14.06.21; TK Gristmill Software: Overland Park, KS, 2014, (aim.tkgristmill.com).
33. Glendening, E. D.; Landis, C. R.; Weinhold, F. NBO 6.0: Natural Bond Orbital Analysis Program J. Comput. Chem. 2013, 34, 1429-1437
34. Lu, T.; Chen, F. Multiwfn: A Multifunctional Wavefunction Analyzer J. Comput. Chem. 2012, 33, 580-592
35. Dennington, R.; Keith, T.; Millam, J. S. GaussView, version 5; Semichem Inc.: Shawnee Mission, KS, 2009.
36. 3MX Molecules (M = C, Si, Ge and X = F, Cl, Br, I) J. Mol. Model. 2012, 1-8
37. Shahi, A.; Arunan, E. Hydrogen Bonding, Halogen Bonding and Lithium Bonding: An Atoms in Molecules and Natural Bond Orbital Perspective Towards Conservation of Total Bond Order, Inter- and Intra-Molecular Phys. Chem. Chem. Phys. 2014, 10.1039/C4CP02585G
38. Salvador, P.; Duran, M.; Mayer, I. One-and Two-Center Energy Components in the Atoms in Molecules Theory J. Chem. Phys. 2001, 115, 1153-1157
39. Lu, Y.-X.; Zou, J.-W.; Wang, Y.-H.; Yu, Q.-S. Theoretical Investigations of the C-X/π Interactions between Benzene and Some Model Halocarbons Chem. Phys. 2007, 334, 1-7
40. Koch, U.; Popelier, P. L. A. Characterization of C-H-O Hydrogen Bonds on the Basis of the Charge Density J. Phys. Chem. 1995, 99, 9747-9754
41. 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. Engl. 1984, 23, 627-628
42. Espinosa, E.; Alkorta, I.; Elguero, J.; Molins, E. From Weak to Strong Interactions: A Comprehensive Analysis of the Topological and Energetic Properties of the Electron Density Distribution Involving XH⋯FY Systems J. Chem. Phys. 2002, 117, 5529-5542
43. Amezaga, N. J. M.; Pamies, S. C.; Peruchena, N. l. M.; Sosa, G. L. Halogen Bonding: A Study Based on the Electronic Charge Density J. Phys. Chem. A 2009, 114, 552-562
44. Johnson, E. R.; Keinan, S.; Mori-Sanchez, P.; Contreras-Garcia, J.; Cohen, A. J.; Yang, W. Revealing Noncovalent Interactions J. Am. Chem. Soc. 2010, 132, 6498-6506