IR Spectroscopic study of hydrogen bonding using a metal carbonyl probe

Abstract

The interaction of different hydrogen bond donors with [M(CO)₅L] [L = (E )-1,2-di-4-pyridylethene, M = Cr or W] was studied by means of IR spectroscopy. A clear shift to higher wavenumbers of the E and A₁ carbonyl vibration modes upon addition of the hydrogen bond donors is observed. The binding isotherms allowed calculation of both the equilibrium constants and free energies of formation of the adducts. These parameters depend on the nature of the carbonyl compound used, the pK_a of the hydrogen bond donor and the steric hindrance of its A–H bond.

References

1. D. Hadzi, Hydrogen Bonding, Pergamon, London, 1959; G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures, Springer, Berlin, 1991; P. Schuster, G. Zundel and C. Sandorfy, The Hydrogen Bond, North-Holland, Amsterdam, 1976; M. C. Etter, Acc. Chem. Res., 1990, 23, 120.
2. P. L. Huyskens, W. A. Luck and T. Zeegers-Huyskens, Intermolecular Forces; An Introduction to Modern Methods and Results, Springer, Berlin, 1991; A. V. Ioagansen, Hydrogen Bond, Nauka, Moscow, 1981; A. V. Iogansen, G. A. Kurkchi, V. M. Furman, V. P. Glazunov and S. E. Odinokov, Prikl. Spektrosk., 1980, 33, 460; R. M. Badger and S. H. Bauer, J. Chem. Phys., 1937, 5, 839.
3. D. Braga, F. Grepioni, E. Tedesco, K. Biradha and G. R. Desiraju, Organometallics, 1996, 15, 2692; 1997, 16, 1846; D. Braga and F. Grepioni, Acc. Chem. Res., 1997, 30, 81; D. Zhao, F. T. Ladipo, J. Bradock-Wilking, L. Brammer and P. Sherwood, Organometallics, 1996, 15, 1441; S. G. Kazarian, P. A. Hamley and M. Poliakoff, J. Am. Chem. Soc., 1993, 115, 9069; J. Chem. Soc., Chem. Commun., 1992, 994; L. M. Epstein, A. N. Krylov, A. Z. Kreindlin, M. I. Rubinskaya and E. S. Shubina, J. Mol. Struct., 1993, 301, 1; L. M. Epstein, A. N. Krylov and E. S. Shubina, J. Mol. Struct., 1994, 322, 345.
4. E. Peris, J. C. Lee, J. R. Rambo, O. Eisenstein and R. H. Crabtree, J. Am. Chem. Soc., 1995, 117, 3485; B. P. Patel, J. Wessel, W. Yao, J. C. Lee, E. Peris, T. F. Koeztle, G. P. A. Yap, J. B. Fortin, J. S. Ricci, G. Sini, A. Albinati, O. Eisenstein, A. L. Rheingold and R. H. Crabtree, New J. Chem., 1997, 21, 413; E. Peris, J. C. Lee and R. H. Crabtree, J. Chem. Soc., Chem. Commun., 1994, 2573; E. Peris, J. Wessel, B. P. Patel and R. H. Crabtree, J. Chem. Soc., Chem. Commun., 1995, 2175; E. Peris and R. H. Crabtree, J. Chem. Soc., Chem. Commun., 1995, 2179; J. C. Lee, E. Peris, A. L. Rheingold and R. H. Crabtree, J. Am. Chem. Soc., 1994, 116, 11014; J. Wessel, J. C. Lee, E. Peris, T. F. Koeztle, G. P. A. Yap, J. B. Fortin, J. S. Ricci, A. Albinati, O. Eisenstein, A. L. Rheingold and R. H. Crabtree, Angew. Chem., Int. Ed. Engl., 1995, 34, 2507.
5. E. A. Shubina, N. V. Belkova, A. N. Krylov, E. V. Vorontsov, L. M. Epstein, D. G. Gusev, M. Niedermann and H. Berke, J. Am. Chem. Soc., 1996, 118, 1105; L. M. Epstein, E. S. Shubina, E. V. Bakhmutova, L. N. Saitkulova, V. I. Bakhmutov, A. L. Chistiakov and I. V. Stankevich, Inorg. Chem., 1998, 37, 3013.
6. D. Braga, P. De Leonardis, F. Grepioni, E. Tedesco and M. J. Calhorda, Inorg. Chem., 1998, 37, 3337.
7. C. E. Anson, T. J. Baldwin, C. S. Creaser, M. A. Fey and R. Stephenson, Organometallics, 1996, 15, 1451.
8. W. Kaim, Angew. Chem., Int. Ed. Engl., 1983, 22, 171.
9. P. S. Bratterman, Metal Carbonyl Spectra, Academic Press, New York, 1975.
10. E. M. Arnett, L. Joris, E. Mitchell, T. S. S. R. Murty, T. M. Gorrie and R. Schleyer, J. Am. Chem. Soc., 1970, 92, 2365; H. H. Jaffe, J. Am. Chem. Soc., 1957, 79, 2373.
11. J. J. Turner, F. W. Grevels, S. M. Howdle, J. Jacke, M. T. Haward and W. E. Klotzbücher, J. Am. Chem. Soc., 1991, 113, 8347.
12. K. A. Connors, Binding Constants: The measurement of molecular complex stabilities, Wiley, New York, 1985.
13. H. Lineweaver and D. Burk, J. Am. Chem. Soc., 1934, 56, 658.
14. F. G. Bordwell, Acc. Chem. Res., 1988, 21, 456.
15. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, GAUSSIAN 94, Revision B.1, Gaussian, Inc., Pittsburgh, PA, 1995.
16. A. D. Becke, (a)Phys. Rev. A, 1988, 38, 3098; (b)J. Chem. Phys., 1993, 98, 5648.
17. C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785.
18. B. Miehlich, A. Savin, H. Stoll and H. Preuss, Chem. Phys. Lett., 1989, 157, 200.
19. J. A. Pople, M. Head-Gordon, D. J. Fox, K. Raghavachari and L. A. Curtis, J. Chem. Phys., 1989, 90, 5622; L. A. Curtis, C. Jones, G. W. Trucks, K. Raghavachari and J. A. Pople, J. Chem. Phys., 1990, 93, 2537.
20. H. B. Schlegel, J. Comput. Chem., 1982, 3, 214.
21. H. B. Schlegel, J. Chem. Phys., 1982, 77, 3676.