Measurement of equilibrium constants for complex formation between phenol and hydrogen-bond acceptors by kinetic laser flash photolysis

Journal of the American Chemical Society

Volumn 118, Issue 28, 1996, Pages 6790-6791

  Banks, J T ^a   Ingold, K U ^a   Lusztyk, J ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL;

ARTICLE; CHEMICAL REACTION KINETICS; EQUILIBRIUM CONSTANT; HYDROGEN BOND; LASER; PHOTOLYSIS;

EID: 0029680920     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961032i     Document Type: Article

References (24)

1. Issued as NRCC No. 39108.
2. NRCC Research Associate 1994-96.
3. (a) Pimental, G. C.; McClellan, A. L. The Hydrogen Bond ; W. H. Freeman and Co.: San Francisco, 1960.
4. (b) Joesten, M. D.; Schaad, L. J. Hydrogen Bonding; Marcell Dekker: New York, 1974.
5. (c) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer Verlag: Berlin, 1991.
6. Except, of course, for studies of self-association where both the HBD and HBA are DOH.
7. 4 is. itself, a weak HBA.
8. 3SiOH), vide infra.
9. Compiled by Dr. Merete F. Nielsen, Department of Chemistry, University of Copenhagen. We thank Dr. Nielsen for sharing the fruits of her labor with us.
10. Avila. D. V.; Ingold, K., U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 466-470.
11. Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Green, W. H.; Procopio, D. R. J. Am. Chem. Soc. 1995, 117, 2929-2930.
12. Valgimigli, L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc: 1995, 117, 9966-9971.
13. MacFaul, P. A.; Ingold, K. U.; Lusztyk, J. J. Org. Chem. 1996, 61, 1316-1321.
14. Valgimigli, L.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. To be submitted for publication.
15. 11
16. • other than the reaction with PhOH. The end of the abscissa corresponds to the neat solvent.
17. • and the last absorbed too strongly at 308 nm, the laser wavelength.
18. 2NCHO, 1.0.
19. Rouviére, J.; Salvinen, J. J. Chim. Phys., Phys.-Chim. Biol. 1969, 66, 149-153.
20. 17
21. -1, respectively. For relatively weak HBA's the normal IR method gives larger equilibrium constants than the kinetic method (vide supra and Table 1) rather than smaller. It would appear that reliable equilibrium constants for hydrogen bonding between phenols and alcohols cannot be obtained by IR spectroscopy.
22. Laurence, C.; Berthelot, M.; Helbert, M.; Sraidi, K. J. Phys. Chem. 1989, 93, 3799-3802.
23. Taft, R. W.; Gurka, D.; Joris, L.; Schleyer, P. v. R.; Rakshys, J. W. J. Am. Chem. Soc. 1969, 91, 4801-4807.
24. -1). This band is well separated from the O-H band for phenol.