The nature and magnitude of specific halogen bonds between iodo-perfluorobenzene and heterocyclic systems

International Journal of Quantum Chemistry

Volumn 111, Issue 10, 2011, Pages 2352-2358

  Lu, Junming ^a   Zhang, Bo ^a   Deng, Qingming ^a   Wang, Jinan ^b   Lu, Yunxiang ^b   Zhu, Weiliang ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

ab initio; halogen bonds; interaction energies; NBO

Indexed keywords

AB INITIO; ATOMS-IN-MOLECULES ANALYSIS; BOND CRITICAL POINTS; FIRST PRINCIPLE CALCULATIONS; HALOGEN BONDING; HALOGEN BONDS; HETEROCYCLIC SYSTEMS; INTERACTION ENERGIES; INTERMOLECULAR DISTANCE; MODEL SYSTEM; NATURAL BOND ORBITAL; NBO; ORBITAL INTERACTION; SUPRAMOLECULAR ARCHITECTURES; SYNTHONS; VAN DER WAALS RADIUS;

ATOMS; CALCULATIONS; CHARGE TRANSFER; HALOGEN ELEMENTS; HYDROGEN BONDS; ION EXCHANGE; ORBITAL TRANSFER; VAN DER WAALS FORCES;

COMPLEXATION;

EID: 79955379081     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.22520     Document Type: Article

References (46)

1. Desiraju, D. R., Angew Chem Int Ed 1995, 34, 2311.
2. Lehn, J.-M., Suparmolecular Chemistry: Concepts and Perspective; Wiley-VCH: Weinheim, 1995.
3. Metrangolo, P.; Resnati, G., Halogen Bonding: Fundamentals and Applications; Springer: Berlin, 2008.
4. Metrangolo, P.; Resnati, G., Chem Eur J 2001, 7, 2511.
5. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G., Acc Chem Res 2005, 38, 386 and references therein.
6. Metrangolo, P.; Resnati, G.; Pilati, T.; Liantonio, R.; Meyer, F., J Polym Sci Part A: Polym Chem 2007, 45, 1 and references therein.
7. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G., Angew Chem Int Ed 2008, 47, 6114 and references therein.
8. Metrangolo, P.; Resnati, G., Science 2008, 321, 918.
9. Cincic, D.; Friscic, T.; Jones, W., Chem Eur J 2008, 14, 747.
10. Voth, A. R.; Hays, F. A.; Ho, P. S., Proc Natl Acad Sci USA 2007, 104, 6188.
11. Trogden, G.; Murray, J. S.; Concha, M. C., J Mol Model 2007, 13, 313.
12. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S., J Mol Model 2007, 13, 305.
13. Clark, T.; Hennemann, M.; Murray, J. S.; Politzer, P., J Mol Model 2007, 13, 291.
14. Murray, J. S.; Lane, P.; Clark, T.; Politzer, P., J Mol Model 2007, 13, 1033.
15. Murray, J. S.; Lane, P.; Politzer, P., Int J Quantum Chem 2007, 107, 2286.
16. Aakeröy, C. B.; Fasulo, M.; Schultheiss, N.; Desper, J.; Moore, C., J Am Chem Soc 2007, 129, 13772.
17. Bouchmella, K.; Boury, B.; Dutremez, S. G.; van der Lee, A., Chem Eur J 2007, 13, 6130.
18. Valerio, G.; Raos, G.; Meille, S. V.; Metrangolo, P.; Resnati, G., J Phys Chem A 2000, 104, 1617.
19. Wang, W. Z.; Wong, N.-B.; Zheng, W. X.; Tian, A. M., J Phys Chem A 2004, 108, 17995.
20. Zou, J. W.; Jiang, Y. J.; Guo, M.; Hu, G. X.; Zhang, B.; Liu, H. C.; Yu, Q. S., Chem Eur J 2005, 11, 740.
21. Lu, Y. X.; Zou, J. W.; Wang, H. Q.; Yu, Q. S.; Zhang, H. X.; Jiang, Y. J., J Phys Chem A 2007, 111, 10781.
22. Bilewicz, E.; Grabowski, S. J., Chem Phys Lett 2006, 427, 51.
23. Awwadi, F. F.; Willett, R. D.; Peterson, K. A.; Twamley, B., Chem Eur J 2006, 12, 8152.
24. Riley, K. E.; Merz, K. M., J Phys Chem A 2007, 111, 1688.
25. Riley, K. E.; Hobza, P., J Chem Theory Comput 2008, 4, 232.
26. Wang, W. Z.; Hobza, P., J Phys Chem A 2008, 112, 4114.
27. Shishkin, O. V., Chem Phys Lett 2008, 458, 96.
28. Li, Q. Z.; Lin. Q. Q.; Li, W. Z.; Cheng, J. B.; Suo, J. Z., ChemPhysChem 2008, 9, 2265.
29. Lu, Y.; Shi, T.; Wang, Y.; Yang H.; Yan, X.; Luo, X.; Jiang, H.; Zhu, W., J Med Chem 2009, 52, 2854.
30. Lu, Y. X.; Zou, J. W.; Wang, H. Q.; Yu, Q. S.; Zhang, H. X.; Jiang, Y. J., J Phys Chem A 2005, 109, 11956.
31. Palusiak, M.; Grabowski, S. J., Struct Chem 2008, 19, 5.
32. Alkorta, I.; Blanco, F.; Solimannejad, M.; Elguero, J., J Phys Chem A 2008, 112, 10856.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr. ; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A., Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2003.
34. Perdew, J. P.; Burke, K.; Ernzerhof, M., Phys Rev Lett 1996, 77, 3865.
35. Lu, Y. X.; Zou, J. W.; Fan, J. C.; Zhao, W. N.; Jiang, Y. J.; Yu, Q. S., J Comput Chem 2009, 30, 725.
36. Moller, C.; Plesset, M. S., Phys Rev 1934, 46, 618.
37. Reiling, S.; Besnard, M.; Bopp, P. A., J Phys Chem A 1997, 101, 4409.
38. Esseffar, M.; Bouab, W.; Lamsabhi, A.; Abboud, J.-L. M.; Notario, R.; Yáñez, M., J Am Chem Soc 2000, 122, 2300.
39. El Firdoussi, A.; Bouab, W.; Esseffar, M.; Alcamí, M.; Yáñez, M.; Abboud, J.- L. M., New J Chem 2001, 25, 509.
40. Shi, Q. C.; Lu, Y. X.; Fan, J. C.; Zou, J. W.; Wang, Y. H., J Mol Struct: Theochem 2008, 853, 39.
41. Boys, S. F.; Bernardi, F., Mol Phys 1970, 19, 553.
42. Reed, A. E.; Curtiss, L. A.; Weinhold, F., Chem Rev 1988, 88, 899.
43. Biegler-Konig, F., AIM 2000 Version 1.0; University of Applied Science: Bielefeld, Germany, 1998-2000.
44. Bondi, A., J Phys Chem 1964, 68, 441.
45. Grabowski, S. J., J Phys Org Chem 2004, 17, 18.
46. Popelier, P. L. A., J Phys Chem A 1998, 102, 1873.