Estimating stacking interaction energy using atom in molecules properties: Homodimers of benzene and pyridine

International Journal of Quantum Chemistry

Volumn 112, Issue 18, 2012, Pages 3008-3017

  Zhikol, Oleg A ^a   Shishkin, Oleg V ^a,b  

^a INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

^b V N KARAZIN KHARKIV NATIONAL UNIVERSITY   (Ukraine)

Author keywords

atoms in molecules; benzene dimer; electron density; polylinear correlation; pyridine dimer; stacking interaction energy

Indexed keywords

ATOM IN MOLECULES; ATOM-ATOM INTERACTION; ATOMS IN MOLECULES; BENZENE DIMERS; CRITICAL POINTS; HOMODIMERS; INTERACTING MOLECULES; MAXIMUM ABSOLUTE ERROR; STACKING INTERACTION ENERGIES;

BENZENE; CARRIER CONCENTRATION; ELECTRON DENSITY MEASUREMENT; MODEL STRUCTURES; PYRIDINE; QUANTUM CHEMISTRY;

HYDROGEN BONDS;

EID: 84864448848     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.24189     Document Type: Article

References (62)

1. A. D. McNaught, A. Wilkinson, Eds. IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"); Blackwell Scientific Publications: Oxford, 1997.
2. R. Custelcean, E. J. James, Chem. Rev. 2001, 101, 1963.
3. P. Politzer, P. Lane, M. C. Concha, Y. Ma, J. S. Murray, J. Mol. Model. 2007, 13, 305.
4. P. Hobza, K. S. Kim, P. Tarakeshwar, J. Y. Lee, Chem. Rev. 2000, 100, 4145.
5. P. Hobza, Editorial: Phys. Chem. Chem. Phys. 2008, 10, 2581.
6. P. O. Ts'o, In Basic Principles in Nucleic Acid Chemistry, Vol. 1;, P. O. Ts'o, Ed.; Academic Press: NY, 1974; pp. 454.
7. S. Marsili, R. Chelli, V. Schettino, P. Procacci, Phys. Chem. Chem. Phys. 2008, 10, 2673.
8. G. R. Desiraju, Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
9. M. Rubeš, O. Bludský, Phys. Chem. Chem. Phys. 2008, 10, 2611.
10. L. F. Lindoy, I. M. Atkinson, Self-assembly in Supramolecular Systems; Cambridge University Press: Cambridge, UK, 2000.
11. S. Grimme, J. Comput. Chem. 2004, 25, 1463.
12. A. D. Becke, E. R. Johnson, J. Chem. Phys. 2007, 127, 124108.
13. Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215.
14. S. F. Boys, F. Bernardi, Mol. Phys. 1970, 19, 553.
15. F. B. van Duijneveldt, J. G. C. M. van Duijneveldt-van de Rijdt, J. H. van Lenthe, Chem. Rev. 1994, 94, 1873.
16. R. F. W. Bader, Atoms in Molecules: A Quantum Theory; Clarendon Press: Oxford, 1990.
17. E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett. 1998, 285, 170.
18. K. A. Lyssenko, M. Yu. Antipin, Russ. Chem. Bull. 2006, 1, 1.
19. L. Sobczyk, S. J. Grabowski, T. M. Krygowski, Chem. Rev. 2005, 105, 3513.
20. K. A. Lyssenko, A. A. Korlyukov, M. Yu. Antipin, Mendeleev Commun. 2005, 15, 90.
21. E. A. Pidko, R. A. van Santen, ChemPhysChem. 2006, 7, 1657.
22. E. A. Pidko, J. Xu, B. L. Mojet, L. Lefferts, I. R. Subbotina, V. B. Kazansky, R. A. van Santen, J. Phys. Chem. B 2006, 110, 22618.
23. A. O. Borissova, A. A. Korlyukov, M. Yu. Antipin, K. A. Lyssenko, J. Phys. Chem. A 2008, 112, 11519.
24. L. N. Puntus, K. A. Lyssenko, M. Yu. Antipin, J.-C. G. Bunzli, Inorg. Chem. 2008, 47, 11095.
25. Yu. V. Nelyubina, M. Yu. Antipin, K. A. Lyssenko,. Russ. Chem. Rev. 2010, 79, 167.
26. S. J. Grabowski, J. M. Ugalde,. J. Phys. Chem. A 2010, 114, 7223.
27. P. Tarakeshwar, K. S. Kim, B. Brutschy, J. Chem. Phys. 2000, 112, 1769.
28. I. S. Bushmarinov, V. P. Morgaliuk, A. A. Korlyukov, M. Yu. Antipin, E. E. Nifant'ev, K. A. Lyssenko, Cryst. Eng. Comm. 2010, 12, 186.
29. R. Bianchi, A. Forni, T. Pilati, Chem.-Eur. J. 2003, 9, 1631.
30. A. Forni, J. Phys. Chem. A 2009, 113, 3403.
31. N. V. Alekseev, E. A. Chernyshev, J. Struct. Chem. 2010, 51, 419.
32. O. V. Shishkin, R. I. Zubatyuk, V. V. Dyakonenko, C. Lepetit, R. Chauvin, Phys. Chem. Chem. Phys. 2011, 13, 6837.
33. J. Overgaard, C. Jones, A. Stasch, B. B. Iversen, J. Am. Chem. Soc. 2009, 131, 4208.
34. T. S. Koritsanszky, P. Coppens, Chem. Rev. 2001, 101, 1583.
35. R. F. W. Bader, H. Essen, J. Chem. Phys. 1984, 80, 1943.
36. R. F. W. Bader, H. J. T. Preston,. Int. J. Quantum Chem. 1969, 3, 327.
37. E. Espinosa, I. Alkorta, I. Rozas, J. Elguero, E. Molins, Chem. Phys. Lett. 2001, 336, 457.
38. I. S. Konovalova, Yu. V. Nelyubina, K. A. Lyssenko, B. V. Paponov, O. V. Shishkin, J. Phys. Chem. A 2011, 115, 8550.
39. O. A. Zhikol, O. V. Shishkin, K. A. Lyssenko, J. Leszczynski, J. Chem. Phys. 2005, 122, 144104.
40. M. P. Waller, A. Robertazzi, J. A. Platts, D. E. Hibbs, P. A. Williams,. J. Comput. Chem. 2006, 27, 491.
41. K. Gkionis, J. A. Platts, J. G. Hill, Inorg. Chem. 2008, 47, 3893.
42. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian03, Revision A.1; Gaussian, Inc.: Pittsburgh, PA, 2003.
43. G. O. Sørensen, L. Mahler, N. Rastrup-Andersen, J. Mol. Struct. 1974, 20, 119.
44. E. F. Archibong, A. J. Thakkar, Mol. Phys. 1994, 81, 557.
45. A. Destexhe, J. Smets, L. Adamowicz, G. Maes, J. Phys. Chem. 1994, 98, 1506.
46. R. D. Johnson, III, Ed. NIST Computational Chemistry Comparison and Benchmark Database, NIST Standard Reference Database Number 101, Release 15b, 2011, Available at:, accessed January 21, 2012.
47. F. Biegler-König, J. Schönbohm, D. Bayles, J. Comput. Chem. 2001, 22, 545.
48. StatSoft, Inc., STATISTICA (data analysis software system), version 8.0, 2008, Available at:, accessed January 21, 2012.
49. J. Gauss, J. F. Stanton, J. Phys. Chem. A 2000, 104, 2865.
50. E. C. Lee, D. Kim, P. Jurečka, P. Tarakeshwar, P. Hobza, K. S. Kim, J. Phys. Chem. A 2007, 111, 3446.
51. B. K. Mishra, J. S. Arey, N. Satyamurthy, J. Phys. Chem A 2010, 114, 9606.
52. M. Piacenza, S. Grimme, ChemPhysChem. 2005, 6, 1554.
53. T. C. Dinadayalane, J. Leszczynski, J. Chem. Phys. 2009, 130, 081101.
54. B. K. Mishra, N. Sathyamurthy, J. Phys. Chem. A 2005, 109, 6.
55. E. G. Hohenstein, C. D. Sherrill, J. Phys. Chem. A 2009, 113, 878.
56. B. Jeziorski, R. Moszynski, K. Szalewicz, Chem. Rev. 1994, 94, 1887.
57. T. K. Venkatachalama, E. Sudbecka, F. M. Uckun, J. Mol. Struct. 2005, 751, 41.
58. M. H. Kutner, C. J. Nachtsheim, J. Neter, W. Li, Applied Linear Regression Models, 5th ed.; McGraw-Hill/Irwin: NY, 2005.
59. J. D. Dunitz, A. Gavezzotti, Angew. Chem. Int. Ed. 2005, 44, 1766.
60. A. Martín Pendás, M. A. Blanco, E. Francisco, J. Comput. Chem. 2007, 28, 161.
61. E. R. Johnson, S. Keinan, P. Mori-Sánchez, J. Contreras- García, A. J. Cohen, W. Yang, J. Am. Chem. Soc. 2010, 132, 6498.
62. J. Contreras-García, E. R. Johnson, S. Keinan, R. Chaudret, J.-P. Piquemal, D. N. Beratan, W. Yang, J. Chem. Theory Comput. 2011, 7, 625.