Protonation of ferrocene, ruthenocene, and osmocene: A density functional study

Russian Chemical Bulletin

Volumn 51, Issue 10, 2002, Pages 1900-1908

  Borisov, Yu A ^a   Ustynyuk, N A ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Density functional theory; Electrophilic substitution; Ferrocene; Hydrogen isotope exchange; Onsager principle of microscopic reversibility; Osmocene; Proton affinity; Rearrangements; Regioselectivity of protonation; Ruthenocene; Sigmatropic hydrogen shifts

Indexed keywords

CATION; CYCLOPENTADIENE DERIVATIVE; FERROCENE; METAL; OSMOCENE; RUTHENOCENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CALCULATION; CHEMICAL BOND; CHEMICAL STRUCTURE; DENSITY; ELECTRIC POTENTIAL; ION EXCHANGE; MOLECULAR INTERACTION; PROTON TRANSPORT;

EID: 0036453971     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1021312820893     Document Type: Article

References (40)

1. W. E. Watts, in Comprehensive Organometallic Chemistry; Eds. G. Wilkinson, F. G. A. Stone, and E. N. Abel, Pergamon, New York, 1982, 8, Ch. 59, 1019.
2. J. H. Richards, Abstr. 135-th Meeting Am. Chem. Soc., April 1959, 86.
3. R. A. Benkeser, Y. Nagai, and J. Hooz, J. Am. Chem. Soc., 1964, 86, 3742.
4. K. L. Rinehart, D. E. Bublitz, and D. H. Gustafson, J. Am. Chem. Soc., 1963, 85, 970.
5. M. Rosenblum and F. W. Abbate, J. Am. Chem. Soc., 1966, 88, 4178.
6. J. C. Ware and T. G. Traylor, Tetrahedron Lett., 1965, 1295.
7. M. Rosenblum, J. O. Santer, and W. G. Howells, J. Am. Chem. Soc., 1963, 85, 1450.
8. T. J. Curphey, J. O. Santer, and M. Rosenblum, J. Am. Chem. Soc., 1960, 82, 5249.
9. E. G. Perevalova and T. V. Nikitina, in Organometallic Reactions, Eds. E. I. Becker and M. Tsutsui, Wiley-Interscience, New York, 1972, 4, 175.
10. A. F. Cunningham, J. Am. Chem. Soc., 1991, 113, 4864.
11. A. F. Cunningham, Organometallics, 1994, 13, 2480.
12. A. F. Cunningham, Organometallics, 1997, 16, 1114.
13. U. T. Mueller-Westerhoff, G. F. Haas, G. F. Swiegers, and T. K. Leipert, J. Organomet. Chem., 1994, 472, 229.
14. M. L. McKee, J. Am. Chem. Soc., 1993, 115, 2818.
15. M. J. Mayor-Lopez, J. Weber, B. Mannfors, and A. F. Cunningham, Organometallics, 1998, 17, 4983.
16. M. J. Mayor-Lopez, H. P. Luthi, H. Koch, P. Y. Morgantini, and J. Weber, J. Chem. Phys., 2000, 113, 8009.
17. A. Karlsson, A. Broo, and P. Ahlberg, Can. J. Chem., 1999, 77, 628.
18. A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
19. C. Lee, W. Yang, and R. G. Parr, Phys. Rev., B, 1988, 150, 785.
20. Niu Shuqiang and M. B. Hall, Chem. Rev., 2000, 100, 353.
21. T. H. Dunning, Jr. and P. J. Hay, in Modern Theoretical Chemistry, Ed. H. F. Schaefer III, Plenum, New York, 1976, 1.
22. P. J. Hay and W. R. Wadt, J. Chem. Phys., 1985, 82, 270.
23. C. Peng and H. B. Schlegel, Israel J. Chem., 1993, 33, 449.
24. GAUSSIAN 98, Revision A. 5, Gaussian, Inc., Pittsburgh PA, 1998.
25. M. S. Foster and J. L. Beuchamp, J. Am. Chem. Soc., 1975, 97, 4814.
26. M. G. Ikonomou, J. Sunner, and P. Kebarle, J. Phys. Chem., 1988, 92, 6308.
27. M. Meot-Ner (Mautner), J. Am. Chem. Soc., 1989, 111, 2830.
28. D. M. P. Mingos, in Comprehensive Organometallic Chemistry, Eds. G. Wilkinson, F. G. A. Stone, and E. N. Abel, Pergamon: New York, 1982, 3, Ch. 19.4.5.
29. R. H. Crabtree and D. G. Hamilton, Adv. Organomet. Chem., 1968, 28, 299.
30. J. A. M. Simões and J. L. Beauchamp, Chem. Rev., 1990, 90, 629.
31. L. M. Epshtein, L. D. Ashkinadze, S. O. Rabicheva, and L. A. Kazitsyna, Doklady Akad. Nauk SSSR, 1970, 190, 128 [Dokl. Chem., 1970 (Engl. Transl.)].
32. L. M. Epshtein, L. D. Ashkinadze, S. O. Rabicheva, and L. A. Kazitsyna, Doklady Akad. Nauk SSSR, 1970, 190, 128 [Dokl. Chem., 1970 (Engl. Transl.)].
33. B. Floris, G. Illuminati, and G. Ortaggi, Tetrahedron Lett., 1972, 269.
34. G. Gerichelli, G. Illuminati, G. Ortaggi, and A. M. Giuliani, J. Organomet. Chem., 1977, 127, 357.
35. T. E. Bitterwolf and A. C. Ling, J. Organomet. Chem., 1972, 40, 197.
36. L. M. Epshtein and E. S. Shubina, Metalloorg. Khim., 1992, 5, 61 [Organomet. Chem. USSR, 1992, 5 (Engl. Transl.)].
37. L. M. Epshtein and E. S. Shubina, Metalloorg. Khim., 1992, 5, 61 [Organomet. Chem. USSR, 1992, 5 (Engl. Transl.)].
38. L. M. Epstein, A. N. Krylov, and E. S. Shubina, J. Mol. Struct., 1999, 322, 345.
39. V. N. Setkina and D. N. Kursanov, Usp. Khim., 1968, 37, 1729 [Russ. Chem. Rev., 1968, 37 (Engl. Transl.)].
40. V. N. Setkina and D. N. Kursanov, Usp. Khim., 1968, 37, 1729 [Russ. Chem. Rev., 1968, 37 (Engl. Transl.)].