Anion-π aromatic neutral tweezers complexes: Are they stable in polar solvents?

Journal of Physical Chemistry A

Volumn 115, Issue 10, 2011, Pages 2016-2025

  Sánchez Lozano, Marta ^a   Otero, Nicolás ^a   Hermida Ramón, Jose M ^a   Estévez, Carlos M ^a   Mandado, Marcos ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANION RECOGNITION; BEFORE AND AFTER; COMPLEX ENERGY; COMPLEX STABILITY; COMPLEX TERM; COMPUTATIONAL METHODOLOGY; ELECTRON DENSITY ANALYSIS; ELECTRON-WITHDRAWING ABILITY; HALIDE ANIONS; INTERACTION ENERGIES; LARGE DIELECTRIC CONSTANT; MOLECULAR TWEEZERS; POLAR SOLVENTS; RESONANCE STRUCTURE; SOLVENT ENVIRONMENTS; SYMMETRY ADAPTED PERTURBATION THEORY;

CYANIDES; DENSITY FUNCTIONAL THEORY; FLUORINE; NEGATIVE IONS; ORGANIC POLYMERS; PERTURBATION TECHNIQUES; SOLVENTS; STABILIZATION;

COMPLEXATION;

FLUORINE; NITRILE; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; QUANTUM THEORY; THERMODYNAMICS;

FLUORINE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITRILES; QUANTUM THEORY; SOLVENTS; THERMODYNAMICS;

EID: 79952601422     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp1096647     Document Type: Article

References (57)

1. Spichiger-Keller, U. S. Chemical Sensors and Biosensors for Medical and Biological Applications; Wiley-VCH: Weinheim, Germany, 1998.
2. Mason, C. F. Biology of Freshwater Pollution, 2 nd ed; Longman: New York, 1991.
3. Steed, J. W. Chem. Commun. 2006, 2637
4. Gale, P. A. Acc. Chem. Res. 2006, 39, 465
5. Bianchi, A.; Bowman-James, K.; Garcia-España, E. Supramolecular Chemistry of Anions; Wiley-VCH: New York, 1997.
6. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486
7. Gorteau, V.; Bollot, G.; Mareda, J.; Perez-Velasco, A.; Matile, S. J. Am. Chem. Soc. 2006, 128, 14788
8. Gorteau, V.; Bollot, G.; Mareda, J.; Matile, S. Org. Biomol. Chem. 2007, 5, 3000
9. Fairchild, R. M.; Holman, T. K. J. Am. Chem. Soc. 2005, 127, 16364
10. Gamez, P.; Mooibroek, T. J.; Teat, S. J.; Reedijk, J. Acc. Chem. Res. 2007, 40, 435
11. Schottel, B. L.; Chifotides, H. T.; Dunbar, K. R. Chem. Soc. Rev. 2008, 37, 68
12. Quinonero, D.; Deya, P. M.; Carranza, M. P.; Rodríguez, A. M.; Jalon, F. A.; Manzano, B. R. Dalton Trans. 2010, 39, 794
13. Berryman, O. B.; Johnson, D. W. Chem. Commun. 2009, 22, 3143
14. Berryman, O. B.; Hof, F.; Hynes, M. J.; Johnson, D. W. Chem. Commun. 2006, 5, 506
15. Rosokha, Y. S.; Lindeman, S. V.; Rosokha, S. V.; Kochi, J. K. Angew. Chem., Int. Ed. 2004, 43, 4650
16. Gil-Ramirez, G.; Escudero-Adan, E. C.; Benet-Buchholz, J.; Ballester, P. Angew. Chem., Int. Ed. 2008, 47, 4114
17. Hermida-Ramón, J. M.; Estévez, C. M. Chem.-Eur. J. 2007, 13, 4743
18. Mandado, M.; Hermida-Ramón, J. M.; Estévez, C. M. THEOCHEM 2008, 854, 1
19. Hermida-Ramón, J. M.; Mandado, M.; Sánchez-Lozano, M.; Estévez, C. M. Phys. Chem. Chem. Phys. 2010, 12, 164
20. Klärner, F. G.; Benkhoff, J.; Boese, R.; Burkert, U.; Kamieth, M.; Naatz, U. Angew. Chem., Int. Ed. 1996, 35, 1130
21. Chen, C. W.; Whitlock, H. W. J. Am. Chem. Soc. 1978, 100, 4921
22. Zimmermann, S. C. Top. Curr. Chem. 1993, 165, 71
23. Kurebayashi, H.; Haino, T.; Usui, S.; Fukazawa, Y. Tetrahedron 2001, 57, 8667
24. Harmata, M. Acc. Chem. Res. 2004, 37, 862
25. Klärner, F. G.; Kahlert, B. Acc. Chem. Res. 2003, 36, 919
26. Etzkorn, M.; Timmerman, J. C.; Brooker, M. D.; Yu, X.; Gerken, M. Beilstein J. Org. Chem. 2010, 6, 39
27. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553
28. Simon, S.; Duran, M.; Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024
29. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
30. Stone, A. J. The Theory of Intermolecular Forces; Clarendon Press: Oxford, 1997.
31. Kaplan, I. G. Intermolecular Interactions: Physical Picture, Computational Methods and Model Potentials; Wiley: West Sussex, 2006.
32. Jeziorski, B.; Moszynski, R.; Szalewicz, K. Chem. Rev. 1994, 94, 1887
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Jr., T. V.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O. D.; Malick, K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
34. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364
35. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. 2005, 109, 4209
36. Kim, J.; Lee, H. M.; Suh, S. B.; Majumdar, D.; Kim, K. S. J. Chem. Phys. 2000, 113, 5259
37. Alkorta, I.; Rozas, I.; Elguero, J. J. Am. Chem. Soc. 2002, 124, 8593
38. Kim, D.; Tarakeshwar, P.; Kim, K. S. J. Phys. Chem. A 2004, 108, 1250
39. Quiñonero, D.; Frontera, A.; Escudero, D.; Ballester, P.; Costa, A.; Deyà, P. M. ChemPhysChem 2007, 8, 1182
40. Quiñonero, D.; Garau, C.; Rotger, C.; Frontera, A.; Ballester, P.; Costa, A.; Deyà, P. M. Angew. Chem., Int. Ed. 2002, 41, 3389
41. Jansen, G.; Hesselmann, A. J. Phys. Chem. A 2001, 105, 646
42. Hesselmann, A.; Jansen, G. Chem. Phys. Lett. 2002, 357, 464
43. Hesselmann, A.; Jansen, G. Chem. Phys. Lett. 2002, 362, 319
44. Hesselmann, A.; Jansen, G. Chem. Phys. Lett. 2003, 367, 778
45. Hesselmann, A.; Jansen, G. Phys. Chem. Chem. Phys. 2003, 5, 5010
46. Hesselmann, A.; Jansen, G.; Schütz, M. J. Chem. Phys. 2005, 122, 014103
47. Szalewicz, K.; Patkowski, K.; Jeziorski, B. Struct. Bonding (Berlin, Ger.) 2005, 116, 43
48. Werner, H.-J.; Knowles, P. J.; Lindh, R.; Manby, F. R.; Schütz, M.; Celani, P.; Korona, T.; Rauhut, G.; Amos, R. D.; Bernhardsson, A.; Berning, A.; Cooper, D. L.; Deegan, M. J. O.; Dobbyn, A. J.; Eckert, F.; Hampel, C.; Hetzer, G.; Lloyd, A. W.; McNicholas, S. J.; Meyer, W.; Mura, M. E.; Nicklass, A.; Palmieri, P.; Pitzer, R.; Schumann, U.; Stoll, H.; Stone, A. J.; Tarroni, R.; Thorsteinsson, T. MOLPRO, version 2006.1, a package of ab initio programs; see http://www.molpro.net.
49. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158
50. Bultinck, P.; Van Alsenoy, C.; Ayers, P. W.; Carbó-Dorca, R. J. J. Chem. Phys. 2007, 126, 144111
51. Bultinck, P.; Ayers, P. W.; Fias, S.; Tiels, K.; Van Alsenoy, C. Chem. Phys. Lett. 2007, 444, 205
52. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833
53. Csizmadia, I. G. Theory and Practice of MO Calculations on Organic Molecules; Elsevier: Amsterdam, 1976.
54. Singh, U. C.; Kollman, P. A. J. Comput. Chem. 1984, 5, 129
55. Bader, R. F. W. Atoms in Molecules-A Quantum Theory, The International Series of Monographs on Chemistry No. 22; Oxford University Press: Oxford, 1990.
56. Biegler-König, F. W.; Schönbohm, J.; Bayles, D. J. Comput. Chem. 2001, 22, 545
57. Rousseau, B.; Peeters, A.; Van Alsenoy, C. Chem. Phys. Lett. 2000, 324, 189