In silico design of heteroaromatic half-sandwich RhI catalysts for acetylene [2+2+2] cyclotrimerization: Evidence of a reverse indenyl effect

Chemistry - A European Journal

Volumn 19, Issue 40, 2013, Pages 13337-13347

  Orian, Laura ^a   Wolters, Lando P ^b   Bickelhaupt, F Matthias ^b,c  

^a UNIVERSITY OF PADOVA   (Italy)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

^c RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

activation strain analysis; catalyst design; cyclotrimerization; density functional calculations; indenyl effect; rhodium

Indexed keywords

ACTIVATION STRAIN; CATALYST DESIGNS; CYCLOTRIMERIZATION; DENSITY FUNCTIONAL THEORY STUDIES; HETEROAROMATIC LIGANDS; INDENYL; STRUCTURE REACTIVITY; STRUCTURE-REACTIVITY RELATIONSHIPS;

ACETYLENE; BENZENE; CATALYSTS; DENSITY FUNCTIONAL THEORY; IONS; LIGANDS; LIGHTING; ORGANOMETALLICS; RHODIUM;

RHODIUM COMPOUNDS;

EID: 84884812065     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301990     Document Type: Article

References (72)

1. G. Schmid, M. Schütz, Organometallics 1992, 11, 1789-1792
2. G. Schmid, M. J. Schütz, J. Organomet. Chem. 1995, 492, 185-189
3. G. Schmid, Comprehensive Heterocyclic Chemistry II, Vol. 3 (Ed.:, I. Shinkai,), Elsevier, Oxford, 1996, Chapter 3.17
4. G. Schmid, B. Kilanowski, R. Boese, D. Bläser, Chem. Ber. 1993, 126, 899-906
5. G. Schmid, F. Schmidt, Chem. Ber. 1986, 119, 1766-1775
6. G. Schmid, D. Kampmann, W. Meyer, R. Boese, P. Paetzold, K. Delpy, Chem. Ber. 1985, 118, 2418-2428
7. G. Schmid, S. Amirkhalili, U. Höner, D. Kampmann, R. Boese, Chem. Ber. 1982, 115, 3830-3841
8. G. Schmid, R. Boese, Z. Naturforsch. B 1983, 38, 485-492
9. G. Schmid, D. Kampmann, U. Höner, D. Blaser, R. Boese, Chem. Ber. 1984, 117, 1052-1060.
10. S.-Y. Liu, M. M.-C. Lo, G. C. Fu, Angew. Chem. 2002, 114, 182-184
11. Angew. Chem. Int. Ed. 2002, 41, 174-176.
12. A. J. Ashe III, X. Fang, Org. Lett. 2000, 2, 2089-2091
13. A. J. Ashe III, X. Fang, J. W. Kampf, Organometallics 2001, 20, 5413-5418
14. X. Fang, H. Yang, J. W. Kampf, M. M. Banaszak Holl, A. J. Ashe III, Organometallics 2006, 25, 513-518.
15. S. Saito, Y. Yamamoto, Chem. Rev. 2000, 100, 2901-2915
16. J. A. Varela, C. Saa, Chem. Rev. 2003, 103, 3787-3801
17. D. L. J. Broere, E. Ruijter, Synthesis 2012, 44, 2639-2672
18. Y. Shibata, K. Tanaka, Synthesis 2012, 44, 3269.
19. P. Cioni, P. Diversi, G. Ingrosso, A. Lucherini, P. Ronca, J. Mol. Catal. 1987, 40, 337-357
20. P. Diversi, L. Ermini, G. Ingrosso, A. Lucherini, J. Organomet. Chem. 1993, 447, 291-298
21. K. Abdulla, B. L. Booth, C. Stacey, J. Organomet. Chem. 1985, 293, 103-114.
22. L. Orian, J. N. P. Van Stralen, F. M. Bickelhaupt, Organometallics 2007, 26, 3816-3830.
23. L. Orian, Rev. Roum. Chim. 2007, 52, 551-558.
24. L. Orian, P. Ganis, S. Santi, A. Ceccon, J. Organomet. Chem. 2005, 690, 482-492
25. L. Orian, A. Bisello, S. Santi, A. Ceccon, G. Saielli, Chem. Eur. J. 2004, 10, 4029-4040
26. S. Santi, L. Orian, A. Bisello, C. Durante, P. Ganis, A. Ceccon, F. Benetollo, L. Crociani, Chem. Eur. J. 2007, 13, 1955-1968
27. S. Santi, L. Orian, C. Durante, E. S. Bencze, A. Bisello, A. Donoli, A. Ceccon, F. Benetollo, L. Crociani, Chem. Eur. J. 2007, 13, 7933-7947
28. S. Santi, C. Durante, A. Donoli, A. Bisello, L. Orian, A. Ceccon, L. Crociani, F. Benetollo, Organometallics 2009, 28, 3319-3326
29. S. Santi, C. Durante, A. Donoli, A. Bisello, L. Orian, F. Benetollo, P. Ganis, A. Ceccon, Organometallics 2010, 29, 2046-2053.
30. M. J. Calhorda, C. C. Romão, L. F. Veiros, Chem. Eur. J. 2002, 8, 868-875.
31. H. Adams, N. A. Bailey, B. E. Mann, B. F. Taylor, C. White, P. Yavari, J. Chem. Soc. Dalton Trans. 1987, 1947-1951
32. A. K. Kakkar, S. F. Jones, N. J. Taylor, S. Collins, T. B. Marder, J. Chem. Soc. Chem. Commun. 1989, 1454-1456
33. S.-Y. Liu, I. D. Hills, G. C. Fu, Organometallics 2002, 21, 4323-4325.
34. P. Hohenberg, W. Kohn, Phys. Rev. 1964, 136, B 864 -B 871
35. W. Kohn, L. J. Sham, Phys. Rev. 1965, 140, A 1133
36. R. G. Parr, W. Yang, Density-Functional Theory of Atoms and Molecules; Oxford University Press, New York, 1989.
37. E. J. Baerends, D. E. Ellis, P. Ros, Chem. Phys. 1973, 2, 41-51.
38. G. te Velde, F. M. Bickelhaupt, E. J. Baerends, C. Fonseca Guerra, S. J. A. van Gisbergen, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931-967
39. Computer code ADF2007 and ADF2012.01: E. J. Baerends, et al. (SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, 2007-2012).
40. E. van Lenthe, E. J. Baerends, J. G. Snijders, J. Chem. Phys. 1994, 101, 9783-9792.
41. A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100
42. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
43. W.-J. van Zeist, F. M. Bickelhaupt, Org. Biomol. Chem. 2010, 8, 3118-3127
44. G. Th. de Jong, F. M. Bickelhaupt, ChemPhysChem 2007, 8, 1170-1181
45. F. M. Bickelhaupt, J. Comput. Chem. 1999, 20, 114-128
46. F. M. Bickelhaupt, E. J. Baerends, in Reviews in Computational Chemistry, Vol. 15 (Eds.:, K. B. Lipkowitz, D. B. Boyd,) Wiley-VCH, Weinheim, 2000, pp. 1-86.
47. G. Th. de Jong, M. Solà, L. Visscher, F. M. Bickelhaupt, J. Chem. Phys. 2004, 121, 9982-9992
48. G. Th. de Jong, D. P. Geerke, A. Diefenbach, F. M. Bickelhaupt, Chem. Phys. 2005, 313, 261-270.
49. G. Th. de Jong, D. P. Geerke, A. Diefenbach, M. Solà, F. M. Bickelhaupt, J. Comput. Chem. 2005, 26, 1006-1020.
50. G. Th. de Jong, F. M. Bickelhaupt, J. Phys. Chem. A 2005, 109, 9685-9699.
51. G. Th. de Jong, F. M. Bickelhaupt, J. Chem. Theory Comput. 2006, 2, 322-335.
52. L. Orian, W. J. van Zeist, F. M. Bickelhaupt, Organometallics 2008, 27, 4028-4030.
53. A. Klamt, G. Schüürmann, J. Chem. Soc. Perkin Trans. 2 1993, 799-805
54. A. Klamt, J. Phys. Chem. 1995, 99, 2224-2235.
55. N. L. Allinger, X. Zhou, J. Bergsma, J. Mol. Struct. THEOCHEM 1994, 312, 69-83.
56. R. S. Bon, B. van Vliet, N. E. Sprenkels, R. F. Schmitz, F. J. J. de Kanter, Chr. V. Stevens, M. Swart, F. M. Bickelhaupt, M. B. Groen, R. V. A. Orru, J. Org. Chem. 2005, 70, 3542-3553.
57. I. Fernández, F. M. Bickelhaupt, F. P. Cossio, Chem. Eur. J. 2012, 18, 12395-12403.
58. C. Amatore, A. Jutand, J. Organomet. Chem. 1999, 576, 254-278.
59. S. Kozuch, S. Shaik, Acc. Chem. Res. 2011, 44, 101-110
60. S. Kozuch, S. Shaik, J. Am. Chem. Soc. 2006, 128, 3355-3356
61. S. Kozuch, S. Shaik, J. Phys. Chem. A 2008, 112, 6032-6041
62. A. Uhe, S. Kozuch, S. Shaik, J. Comput. Chem. 2011, 32, 978-985.
63. L. Orian, M. Swart, F. M. Bickelhaupt, unpublished results.
64. N. E. Schore, Chem. Rev. 1988, 88, 1081-1119.
65. J. H. Hardesty, J. B. Koerner, T. A. Albright, G.-Y. Lee, J. Am. Chem. Soc. 1999, 121, 6055-6067.
66. K. Kirchner, M. J. Calhorda, R. Schmid, L. F. Veiros, J. Am. Chem. Soc. 2003, 125, 11721-11729
67. M. J. Calhorda, P. J. Costa, K. Kirchner, Inorg. Chim. Acta 2011, 374, 24-35
68. Y. Yamamoto, T. Arakawa, R. Ogawa, K. Itoh, J. Am. Chem. Soc. 2003, 125, 12143-12160
69. Y. Yamamoto, K. Kinpara, T. Saigoku, H. Takagishi, S. Okuda, H. Nishiyama, K. Itoh, J. Am. Chem. Soc. 2005, 127, 605-613
70. Y. Yamamoto, K. Kinpara, R. Ogawa, H. Nishiyama, K. Itoh, Chem. Eur. J. 2006, 12, 5618-5631.
71. M. E. Rerek, L. N. Ji, F. Basolo, J. Chem. Soc. Chem. Commun. 1983, 1208.
72. 3 occurs, consistent with what is commonly termed indenyl effect. However, in their case, this absence of slippage and reduced reactivity occurs exactly for the indenyl complex. To avoid overlap in terminology with the effect revealed by us (i.e., reduced reactivity in the case of more slippage of the indenyl ligand) we propose here the slightly different designation of a "reverse indenyl effect"., K. A. Pevear, M. M. Banaszak Holl, G. B. Carpenter, A. L. Rieger, P. H. Rieger, D. A. Sweigart, Organometallics 1995, 14, 512-523.