Substituent Effects on the Bond-Dissociation Energies of Cationic Arene-Transition-Metal Complexes

European Journal of Organic Chemistry

Volumn , Issue 4, 1998, Pages 565-571

  Schroeter, Katrin ^b   Wesendrup, Ralf ^a,b   Schwarz, Helmut ^b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Arenes; Bond dissociation energies; Gas phase chemistry; Ionization energies; Transition metals

Indexed keywords

EID: 0000402928     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199804)1998:4<565::aid-ejoc565>3.0.co;2-j     Document Type: Article

References (43)

1. T. J. Kealy, P. L. Pauson, Nature 1951, 168, 1039.
2. E. O. Fischer, W. Hafner, Z. Naturforsch. 1955, 10b, 665.
3. [3a] Q wilkinson, F. G. A. Stone, E. W. Abel (Eds.), Comprehensive Organometallic Chemistry, vol. 3-6, Pergamon Press, New York, 1982.
4. [3b] For a historical perspective, see: J. D. Dunitz in Organic Chemistry: Its Language and Its State of the Art (Ed.: V. M.. Kisakürek), VHCA, Basel, 1993, p. 9.
5. [3c] D. Braga, P. J. Dyson, F. Grepioni, F. G. Johnson, Chem. Rev. 1994, 94, 1585.
6. [3d] M. L. H. Green, D. K. P. Ng, Chem. Rev. 1995, 95, 439.
7. [4a] F. Meyer, F. A. Khan, P. B. Armentrout, J. Am. Chem. Soc. 1995, 117, 9740.
8. [4b] K. F. Willney, C. S. Yeh, D. L. Robbins, M. A. Duncan, J. Phys. Chem. 1992, 96, 9106.
9. [4c] D. Stöckigt, J. Hrušak, H. Schwarz, Int J. Mass Spectrom. Ion Processes 1995. 149/150, 1.
10. [4d] R. C. Dunbar, S. J. Klippenstein, J. Hrušak, D. Stöckigt, H. Schwarz, J. Am. Chem. Soc. 1996, 118, 5277.
11. [4e] C.-Y Lin, R. C. Dunbar, Organometallics 1997, 16, 2691.
12. [4f] B. P. Poznaik, R. C. Dunbar, J Am. Chem. Soc. 1997, 119, 10439.
13. [5a] C. W. Bauschlicher Jr., H. Partridge, S. R. Langhoff, J. Phys. Chem. 1992, 96, 3273.
14. [5b]N. L. Ma, K. M Ng, C. W. Tsang, Chem. Phys. Lett. 1997, 277, 306.
15. [6a] N. F. Dalleska, K. Honma, L. S. Sunderlin, P. B. Armentrout, J. Am. Chem. Soc. 1994, 116, 3519.
16. [6b] P. B. Armentrout. B. L. Kickel in Organometallic Ion Chemistry (Ed.: B. S. Freiser) Kluwer, Dordrecht, 1995, p. 1.
17. J. Groß, G. Harder, F. Vogtle, H. Stephan, K. Gloe, Angew. Chem. 1995, 107, 523; Angew. Chem. Int. Ed Engl. 1995, 34, 481.
18. J. Groß, G. Harder, F. Vogtle, H. Stephan, K. Gloe, Angew. Chem. 1995, 107, 523; Angew. Chem. Int. Ed Engl. 1995, 34, 481.
19. D. A. Dougherty, Science 1996, 261, 163.
20. [9a] D Schröder, D. Sülzle, J. Hrušak, D. K. Böhme, H. Schwarz, Int. J. Mass Spectrom. Ion Processes 1991, 110, 145.
21. [9b] K. Schroeter, C. A. Schalley, R. Wesendrup, D. Schröder, H. Schwarz, Organometallics 1997, 16, 986.
22. [9c] K. Schroeter, C. A Schalley, D. Schröder, H. Schwarz, Helv. Chim. Acta. 1997, 80, 1205.
23. [10a] R. G. Cooks, T. L Kruger, J. Am. Chem. Soc. 1977, 99, 1279.
24. [10b] For a recent review, see: R. G. Cooks, J. S. Patrick, T Kotiaho, S. A. McLuckey, Mass Spectrom. Rev. 1994, 13, 287.
25. [10c] See also: V.Vekey, J. Mass Spectrom. 1996, 31, 445.
26. [11a] A. Bjarnason, J. W. Taylor, Organometallics 1989, 8. 2020.
27. [11b] Y. Huang, B. S. Freiser, Inorg. Chem. 1990, 29, 2052.
28. [11c] A. Bjarnason, Organometallics 1991, 10, 1244.
29. [11d] A. Bjarnason, Organometallics 1996, 15, 3275.
30. This lower BDE is in qualitative agreement with the smaller rate of formation of neutral fluorobenzene-vanadium clusters: M. Hirano, K. Judai, A. Nakajima, K. Kaya, J. Phys. Chem. A 1997, 101, 4893.
31. As for the fluorotoluenes, the ortho isomer of chlorotoluene is slightly stronger bound; however, the ΔBDE for the different isomers do not exceed the experimental error.
32. See for example: H. C. Brown, J. D. Brady, J. Am. Chem. Soc. 1952, 74, 3570.
33. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165.
34. S. Mecozzi, A. P. West, Jr., D. A. Dougherty. J. Am. Chem. Soc. 1996, 118, 2307.
35. D. R. Lide (Ed.), CRC Handbook of Chemistry and Physics, CRC Press, Boca Raton, 1992.
36. [18b] S. G. Lias, J. F. Liebman, R. D. Levin, S. A. Kafafi, NIST Standard Reference Database, Positive Ion Energetics. Version 2.01, Gaithersburg, MD, January 1994.
37. [18b] S. G. Lias, J. F. Liebman, R. D. Levin, S. A. Kafafi, NIST Standard Reference Database, Positive Ion Energetics. Version 2.01, Gaithersburg, MD, January 1994.
38. [19a] R. Srinivas, D. Sülzle, T. Weiske, H. Schwarz, Int. J. Mass Spectrom. Ion Processes 1991, 707, 368.
39. [19b] R. Srinivas, D. Sülzle, W. Koch, C. H. dePuy, H. Schwarz, J. Am. Chem. Soc. 1991, 113, 5970.
40. [19c] C. A. Schalley, D. Schröder, H. Schwarz, Int. J. Mass Spectrom. Ion Processes 1996, 153, 173.
41. B. A. Rumpf, C. E. Allison, P. J. Derrick, Org. Mass Spectrom. 1986, 21, 295.
42. D. Schröder, H. Schwarz, J. Organomet. Chem 1995, 504, 123.
43. + 2.5 kcal/mol). See also: S. Ma. P. Wong, S. S. Yang, R.G. Cooks, J. Am. Chem. Soc. 1996, 118, 6010.