The relationship between aromaticity and charge-transfer transitions: A combined study of square-planar metal complexes based on DFT, NMR and nucleus-independent chemical shifts

European Journal of Inorganic Chemistry

Volumn , Issue 12, 2006, Pages 2460-2468

  Makedonas, Christodoulos ^a   Mitsopoulou, Christiana A ^a  

^a UNIVERSITY OF ATHENS   (Greece)

Author keywords

Aromaticity; Density functional calculations; N ligands; S ligands; Transition metals

Indexed keywords

AROMATIZATION; CHARGE TRANSFER; CHEMICAL SHIFT; LIGANDS; METAL COMPLEXES; METAL IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TRANSITION METAL COMPOUNDS;

AROMATICITIES; CHARGE TRANSFER TRANSITIONS; DENSITY-FUNCTIONAL CALCULATIONS; GROUP VIII METALS; N LIGANDS; N-LIGANDS; NMR-SPECTROSCOPY; NUCLEUS-INDEPENDENT CHEMICAL SHIFTS; S LIGANDS; SQUARE-PLANAR METALS;

TRANSITION METALS;

EID: 33745661256     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200600114     Document Type: Article

References (72)

1. a) V. I. Minkin, M. N. Glukhovtsev, B. Ya. Simkin, Aromaticity and Antiaromaticity - Electronic and Structural Aspects, Wiley, New York, 1994;
2. b) Special issue on aromaticity: P. v. R. Schleyer (Guest Ed.), Chem. Rev. 2001, 101, 1115-1566.
3. a) P. v. R. Schleyer, H. Jiao, N. J. R. van Eikema Hommes, V. G. Malkin, O. L. Malkina, J. Am. Chem. Soc. 1997, 119, 12669-12670;
4. b) C. Lauterbach, J. Fabian, Eur. J. Inorg. Chem. 1999, 1995-2004;
5. c) G. Liu, Q. Fang, C. Wang, J. Mol. Struct. (THEOCHEM) 2004, 679, 115-120.
6. a) C. S. Wannere, C. Corminboeuf, Z. X. Wang, M. D. Modrich, R. B. King, P. v. R. Schleyer, J. Am. Chem. Soc. 2005, 127, 5701-5705;
7. b) A. I. Boldyrev, L. S. Wang, Chem. Rev. 2005, 105, 3716-3757.
8. a) G. N. Schrauzer, V. R. Mayweg, J. Am. Chem. Soc. 1966, 88, 3235-3242;
9. b) U. T. Mueller-Westerhoff, B. Vance, in Comprehensive Coordination Chemistry (Ed.: G. Wilkinson), Pergamon, Oxford, 1987, vol. 2, pp. 595-631;
10. c) J. H. Enemark, J. J. A. Cooney, J. J. Wang, R. H. Holm, Chem. Rev. 2004, 104, 1175-1200;
11. d) C. Mitsopoulou, J. Konstantatos, D. Katalis, E. J. Vrachnou, Mol. Catal. 1991, 67 137-146;
12. e) S. Curreli, P. Deplano, C. Faulmann, A. Ienco, C. Mealli, M. L. Mercuri, L. Pilia, G. Pintus, A. Serpe, E. F. Trogu, Inorg. Chem. 2004, 43, 5069-5079.
13. D. Argyropoulos, C.-A. Mitsopoulou, D. Katakis, Inorg. Chem. 1996, 35, 5549-5554.
14. D. Argyropoulos, E. Lyris, C.-A. Mitsopoulou, D. Katakis, J. Chem. Soc., Dalton Trans. 1997, 615.
15. T. R. Miller, I. G. Dance, J. Am. Chem. Soc. 1973, 95, 6970-6979.
16. a) M. Hissler, I. E. McGarrah, W. B. Connick, D. K. Geiger, S. D. Cummings, R. Eisenberg, Coord. Chem. Rev. 2000, 208, 115-137;
17. b) S. D. Cummings, R. Eisenberg, J. Am. Chem. Soc. 1996, 118, 1949-1960;
18. c) S. D. Cummings, L.-T. Cheng, R. Eisenberg, Chem. Mater. 1997, 9, 440-450;
19. d) J. A. Zuleta, M. S. Burberry, R. Eisenberg, Coord. Chem. Rev. 1990, 97, 47-64.
20. a) K. Kubo, M. Nakano, H. Tamura, G.-E. Matsubayashi, Inorg. Chim. Acta 2002, 336, 120;
21. b) G. Matsubayashi, M. Nakano, H. Tamura, Coord Chem. Rev. 2002, 226, 143;
22. c) A. Islam, H. Sugihara, K. Hara, L. P. Singh, R. Katoh, M. Yanakida, Y. Takahashi, S. Murata, H. Arakawa, Inorg. Chem. 2001, 40, 5371.
23. a) V. E. Kaasjager, E. Bouwman, S. Gorter, J. Reedijk, C. A. Grapperhaus, J. H. Reibenspies, J. J. Smee, M. Y. Darensbourg, A. Derecskei-Kovacs, L. M. Thomson, Inorg. Chem. 2002, 41, 1837;
24. b) Y. Zhang, K. D. Ley, K. S. Schanze, Inorg. Chem. 1996, 35, 7102;
25. c) K. Base, M. T. Tierney, A. Fort, J. Muller, M. W. Grinstaff, Inorg. Chem. 1999, 38, 287
26. d) Y.-D. Chen, Y.-H. Qin, L.-Y. Zhang, L.-X. Shi, Z.-N. Chen, Inorg. Chem. 2004, 43, 1197-1205;
27. e) Y.-D. Chen, L.-Y. Zhang, L.-X. Shi, Z.-N. Chen, Inorg. Chem. 2004, 43, 7493-7501.
28. a) C. Makedonas, C.-A. Mitsopoulou, J. Inorg. Biochem. 2001, 86, 326;
29. b) C. Makedonas, C.-A. Mitsopoulou, Eur. J. Inorg. Chem. 2006, 590-598;
30. c) C. Makedonas, C.-A. Mitsopoulou, Spectrochim. Acta Part A 2006, 64, 918-930;
31. d) C. Makedonas, C.-A. Mitsopoulou, F. J. Lahoz, A. I. Balana, Inorg. Chem. 2003, 42, 8853-8865.
32. P. v. R. Schleyer, Chem. Rev. 2001, 101, 1115 and references cited therein.
33. a) W. J. Hehre, R. T. McIver, J. A. Pople, P. v. R. Schleyer, J. Am. Chem. Soc. 1974, 96, 7162-7163;
34. b) L. Radom, J. Chem. Soc., Chem. Commun. 1974, 403-404;
35. c) T. M. Krygowski, M. Cyrañski, Tetrahedron 1996, 52, 1713-1722.
36. P. v. R. Schleyer, C. Maerker, A. Drausfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
37. a) G. Subramanian, P. v. R. Schleyer, H. Jiao, Angew. Chem. Int. Ed. Engl. 1996, 35, 2638-2641;
38. b) H. Jiao, P. v. R. Schleyer, R. B. Beno, K. N. Houk, R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 36, 2761-2764;
39. c) A. A. Fokin, H. Jiao, P. v. R. Schleyer, J. Am. Chem. Soc. 1998, 120, 9364-9365;
40. d) T. Zywietz, H. Jiao, P. v. R. Schleyer, A. de Meijere, J. Org. Chem. 1998, 63, 3417;
41. e) S. Patchkovskii, W. Thiel, J. Mol. Mod. 2000, 6, 67-75.
42. a) P. v. R. Schleyer, M. Manoharan, Z.-X. Wang, B. Kiran, H. Jiao, R. Puchta, N. J. R. v. E. Hommes, Org. Lett. 2001, 3, 2465-2468;
43. b) M. K. Cyrañski, T. M. Krygowski, A. R. Karizky, P. v. R. Schleyer, J. Org. Chem. 2002, 67, 1333-1338;
44. c) R. W. A. Havenith, H. Jiao, L. W. Jenneskens, J. H. van Lentle, M. Sarobe, P. v. R. Schleyer, M. Kataoka, A. Necula, L. T. Scott, J. Am. Chem. Soc. 2002, 124, 2363-2370.
45. a) M. Bühl, Chem. Eur. J. 1998, 4, 734-739;
46. b) M. L. McKee, Z. X. Wang, P. v. R. Schleyer, J. Am. Chem. Soc. 2000, 122, 4781-4793;
47. c) A. Hirsch, Z. Chen, H. Jiao, Angew. Chem. Int. Ed. 2000, 39, 3915-3917;
48. d) M. Bühl, A. Hirsch, Chem. Rev. 2001, 101, 1153-1183.
49. P. v. R. Schleyer, B. Kiran, D. V. Simon, T. S. Sorensen, J. Am. Chem. Soc. 2000, 122, 510-513.
50. a) Z. Zhou, R. G. Parr, J. F. Garst, Tetrahedron Lett. 1988, 29, 4843-4846;
51. b) Z. Zhou, R. G. Parr, J. Am. Chem. Soc. 1989, 111, 7371-7379.
52. T. M. Cocker, R. E. Bachman, Inorg. Chem. 2001, 40, 1550-1556.
53. W. B. Connick, H. B. Gray, J. Am. Chem. Soc. 1997, 119, 11620-11627.
54. C. E. Keefer, R. D. Bereman, S. T. Purrington, B. W. Knight, P. D. Boyle, Inorg. Chem. 1999, 38, 2294-2302.
55. a) S. Nishigaki, H. Yoshioka, K. Nakatsu, Acta Crystallogr., Sect. B 1978, 34, 875-879;
56. b) Y.-D. Tian Duan, X.-X. Xu, X.-Z. You, Acta Crystallogr., Sect. C 1995, 51, 2309-2312;
57. c) L. L. Merritt, E. D. Schroeder, Acta Crystallogr. 1956, 12, 801-804.
58. H. Günther, NMR Spectroscopy - Basic Principles, Concepts and Applications in Chemistry, 2nd ed., John Wiley & Sons, Chichester, 1995.
59. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, 3rd ed., Pergamon Press, New York, 1988.
60. R. G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, 1989.
61. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, 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, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.9, Gaussian, Inc., Pittsburgh PA, 1998.
62. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
63. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
64. a) A. D. McLean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639-5648;
65. b) R. Krishnan, J. S. Binkley, R. Seeyer, J. A. Pople, J. Chem. Phys. 1980, 72, 650-654.
66. D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, H. Preuss, Theor. Chim. Acta 1990, 77, 123-141.
67. a) K. Wolinski, J. F. Hilton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251-8260;
68. b) J. L. Dodds, R. McWeeny, A. J. Sadlej, Mol. Phys. 1977, 34, 1779-1791;
69. c) R. Ditchfield, Mol. Phys. 1974, 27, 789;
70. d) R. McWeeny, Phys. Rev. 1962, 126, 1028-1034.
71. a) S. I. Gorelsky, AOMix program, revisions 4.7 and 5.1 http://www.sg-chem.net/aomix/;
72. b) S. I. Gorelsky, A. B. P. Lever, J. Organomet. Chem. 2001, 635, 187-196.