The role of π-π stacking interactions in square planar palladium complexes. Combined quantum mechanics/molecular mechanics QM/MM studies

Organometallics

Volumn 20, Issue 20, 2001, Pages 4178-4184

  Magistrato, Alessandra ^a   Pregosin, Paul S ^a   Albinati, Alberto ^b   Rothlisberger, Ursula ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DISTORTION; MOLECULAR MECHANICS; STACKING INTERACTIONS;

MOLECULAR DYNAMICS; NUMERICAL METHODS; PALLADIUM COMPOUNDS; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY;

ORGANOMETALLICS;

EID: 0035497177     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010485f     Document Type: Article

References (58)

1. Saenger, W. Principles of Nucleic Acid Structures; Springer-Verlag: New York, 1984; p 132.
2. Wakelin, L. P. G. Med. Res. Rev., 1986, 6, 275.
3. Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125.
4. (a) Abraham, R. J.; Eivazi, F.; Pearson, H.; Smith, K. M. J. Chem. Soc., Chem. Commun. 1976, 698.
5. (b) Abraham, R. J.; Eivazi, F.; Pearson, H.; Smith, K. M. J. Chem. Soc., Chem. Commun. 1976, 699.
6. Ranganathan, D.; Haridas, V.; Gilardi, R.; Karle, I. L. J. Am. Chem. Soc. 1998, 120, 10793.
7. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
8. Quantum mechanical calculations on the benzene dimer, e.g., (a) Chipot, C.; Jaffe, R.; Maigret, B.; Pearlman, D. A.; Kollman, P. A. J. Am. Chem. Soc. 1996, 118, 11217.
9. (b) Hobza, P.; Selzle, H. L.; Schlag, E. W. J. Phys. Chem. 1996, 100, 18790.
10. (c) Špirko, V.; Engkvist, O., Soldán, P.; Selzle, H. L.; Schlag, E. W.; Hobza, P. J. Chem. Phys. 1999, 111, 572, have shown a variety of stable minimum configurations: (i) a T-shape structure with the planes of the molecules perpendicular to each other; (ii) a face-to-face geometry with the molecules on top of each other (parallel sandwich); and (iii) a parallel arrangement in which one molecule is shifted with respect to the plane of the other molecule (parallel displaced). The quadrupole-quadrupole interaction plays a significant role in stabilizing the T-shape geometry
11. (Hobza, P.; Zahradník. Intermolecular Complexes; Elsevier: Amsterdam, 1988), whereas in the stacked geometries the dispersion interactions dominate. Moreover, the shifted geometry derives from a compromise between electrostatic and van der Waals interactions.
12. Hobza, P.; Kabeláč, M.; Šponer, J.; Mejzlík, P.; Vondrášek, J. J. Comput. Chem. 1997, 18, 1136.
13. (a) Geremia, S.; Randaccio, L.; Mestroni, G.; Milani, B. J. Chem. Soc., Dalton. Trans. 1992, 2117.
14. (b) Blake, A.; Hubberstey, P.; Li, W. S.; Quinlan, D. J.; Russel, C. E.; Sampson, C. L. J. Chem. Soc., Dalton, Trans. 1999, 4261.
15. (c) Janiak, C.; Deblon, S.; Wu, H. P.; Kolm, M. J. Klüfers, P.; Piotrowski, H.; Mayer, P. Eur. J. Inorg. Chem. 1999, 1507.
16. Cozzi, F.; Ponzini, F.; Annunziata, R.; Cinquini, M.; Siegel, J. S. Angew. Chem. 1995, 107, 1092.
17. (b) Luth, M. S.; Kapinos, L. E.; Song, B.; Lippert, B.; Sigel, H. J. Chem. Soc., Dalton Trans. 1999, 357.
18. (a) Castonguay, L. A.; Rappé, A. K.; Casewit, C. J. J. Am. Chem. Soc. 1991, 113, 7177.
19. (b) Yang, F.; Fanwick, P. E.; Kubiak, C. P. Organometallics 1999, 18, 4222.
20. (c) Selvakumar, K.; Valentini, M.; Pregosin, P. S.; Albinati, A.; Eisenträger, F. Organometallics 2000, 19, 1299.
21. (d) Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P.; Tschoerner, M. J. Am. Chem. Soc. 1997, 119, 6315.
22. (e) Abbenhuis, H. C. L.; Burckhardt, U.; Gramlich, V.; Köllner, C.; Pregosi, P. S.; Salzman, R.; Togni, A. Organometallics 1995, 14, 759.
23. (f) Barbaro, P.; Pregosin, P. S.; Salzman, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160.
24. (g) Janiak, C. J. Chem. Soc., Dalton Trans. 2000, 3885.
25. Magistrato, A.; Merlin, M.; Albinati, A.; Pregosin, P. S., Rothlisberger, U. Organometallics 2000, 19, 3591.
26. Drago, D.; Pregosin, P. S.; Tschoerner, M.; Albinati, A. J. Chem. Soc., Dalton Trans. 1999, 2279.
27. Meijer, E. J.; Sprik, M. J. Chem. Phys., 1996, 105, 8684.
28. (a) Kristyan, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175.
29. (a) Combined Quantum Mechanical and Molecular Mechanical Methods; ACS Symposium Series 712; Gao, J., Thompson, M. A., Eds.; American Chemical Society: Washington, DC, 1998.
30. (b) Rothlisberger, U.; Carloni, P.; Doclo, K.; Parrinello, M. J. Biol. Inorg. Chem. 2000, 5, 36.
31. (c) Rothlisberger, U. Int. J. Quantum Chem. 1999, 73, 209.
32. (d) Carloni, P.; Rothlisberger, U.; Theoretical and Computational Chemistry; Eriksson, L. A. Ed.; Elsevier: New York, 2001; Vol. 9, p 215.
33. (e) Mulholland, A. J.; Lyne, P. D.; Karplus, M. J. Am. Chem. Soc. 2000, 122, 534.
34. (f) Cui, Q.; Karplus, M. J. Am. Chem. Soc. 2001, 123, 2284.
35. (g) Ridder, L.; Mullholland, A. J.; Rietjens, I. M. C. M.; Vervoort, J. J. Am. Chem. Soc. 2000, 122, 8728.
36. (a) Woo, T. K.; Blöchl, P. E.; Ziegler, T. J. Phys. Chem. A 2000, 104, 121.
37. (b) Deng, L.; Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1999, 121, 6479.
38. (c) Margl, P. M.; Woo, T. K.; Ziegler, T. Organometallics 1998, 17, 4997.
39. (d) Milano, G.; Guerra, G.; Pellecchia, C.; Cavallo, L. Organometallics 2000, 19, 1343.
40. (e) Longo, P.; Grisi, F.; Guerra, G.; Cavallo, L. Macromolecules 2000, 33, 4647.
41. In addition, we have already pointed out that there is also a significant structural rearrangement of the aryl ligand due to strong electronic correlations with the P(1)-phenyl ring in pseudo-trans position. The two rings in fact try to maximize their coplanarity within the steric retrictions of the environment.
42. Clark, M.; Cramer, R. D., III; van Opdenbosh N. J. Comput. Chem. 1989, 10, 982.
43. The Mulliken charge analysis has been performed with a double-ζ basis without polarization function for all atoms.
44. (a) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
45. (b) Versluis, L.; Ziegler, T. J. Chem. Phys. 1998, 88, 322.
46. (c) te Velde, G.; Baerends, E. J.; J. Comput. Phys. 1992, 99, 84.
47. (d) Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Theor. Chim. Acc. 1998, 99, 391.
48. Becke, A. Phys. Rev. A 1988, 38, 3098.
49. Perdew, J. P.; Zunger, A. Phys. Chem. Rev. B 1981, 23, 5048.
50. (a) Snijeders, J. G.; Baerends, E. J., J. Mol. Phys. 1978, 36, 1789.
51. (b) Snijeders, J. G.; Baerends, E. J.; Ros, P. Mol. Phys. 1979, 38, 1909.
52. Rappé, A. K. Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
53. Woo, T. K.; Cavallo, L.; Ziegler, T. Theor. Chem. Acc. 1998, 100, 307.
54. SAINT, SAX Area Detector Integration; Siemens Analytical Instrumentation, 1996.
55. Sheldrick, G. M. SADABS; Universität Göttingen.
56. Sheldrick, G. M. SHELX-97, Structure Solution and Refinement Package; Universität Göttingen, 1997.
57. Flack, H. D. Acta Crystallogr. 1983, A 39, 876.
58. International Tables for X-ray Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publisher: Dordrecht, The Netherlands, 1992; Vol. C.