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Low-Barrier Hydrogen Bonds in Pyridine-Dichloroacetic Acid Complexes

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Amixture of Cl2CHCOOH-16O2 and Cl2CHCOOH-18O2 was combined with an excess of a pyridine and studied by NMR at 23_C, -43_C, and -81_C. The 1:1 complexes were analyzed by isotopic perturbation of equilibrium. Plots of OH chemical shift and of 13C isotope shift vs. pKa of the pyridinium ion both exhibit maxima ~ 5, when the basicities of the hydrogen-bond acceptors become matched, the hydrogen bond is strongest, and the equilibrium is maximally perturbed by the isotope. In contrast, for the complexes of pyridine and 3-picoline the isotopic perturbation seems to disappear, consistent with a low-barrier hydrogen bond in a single structure, rather than a hydrogen that can take either of two positions in a mixture of two tautomers.
Rocznik
Strony
1693--1702
Opis fizyczny
Bibliogr. 22 poz., rys.
Twórcy
autor
  • Department of Chemistry, University of California - San Diego, La Jolla, CA 92093-0358, USA
autor
  • Department of Chemistry, University of California - San Diego, La Jolla, CA 92093-0358, USA
autor
  • Department of Chemistry, University of California - San Diego, La Jolla, CA 92093-0358, USA
Bibliografia
  • 1. Jeffrey G.A., An Introduction to Hydrogen Bonding, Oxford, 1997; Scheiner S., Hydrogen Bonding: A Theoretical Perspective, Oxford, 1997.
  • 2. Emsley J., Chem, Soc. Revs., 9, 91 (1980); Hibbert F. and Emsley J., Adv. Phys. Org. Chem., 28, 255 (1990); Dega-Szafran Z. and Szafran M., Heterocycles, 37, 627 (1994).
  • 3. Gilli P., Bertolasi V., Ferretti V. and Gilli G.,J. Am. Chem. Soc., 116. 909 (1994).
  • 4. Gilli P., Bertolasi V., Ferretti V. and Gilli G., J. Am. Chem. Soc., 122, 10405 (2000).
  • 5. Frey P.A., Magn. Reson. Chem., 39, S190 (2001); Westler W.M., Frey P-A-, Lin J., Wemmer D.E., Morimoto H., Williams P.G. and Markley J.L., J. Am. Chem. Soc., 124, 4196 (2002).
  • 6. Perrin C.L. andThobum J.D., J. Am Chem. Soc., 111,8010 (1989); Perrin C.L. andThobum J.D,,J. Am Chem. Soc., 114, 8559 (1992); Perrin C.L., Science, 266, 1665 (1994); Perrin C.L. and Nielson J.B., J Am. Chem. Soc., 119, 12734 (1997).
  • 7. Perrin C.L. and Ohta B.K., J. Am. Chem. Soc., 123, 6520 (2001).
  • 8. Garcia-VilocaM.,Gonzalez-Lafont A. andLluch J.M.,7. Am. Chem. Soc., 121,9198 (1999); Bach R.D. Dmitrenko O. and Glukhovtsev M.N., J. Am. Chem. Soc., 123, 7134 (2001).
  • 9. Perrin C.L. and Ohta B.K., Bioorg. Chem., 30,3 (2002); Perrin C.L. and Ohta B.K., J. Mol. Struct., 644, (2003).
  • 10. Dega-Szafran Z. and Dulewicz E., J. Chem. Soc. Perkin Trans. 2,345 (1983).
  • 11. Gilli P., Bertolasi V., Pretto L., Lycka A. and Gilli G., J. Am. Chem. Soc., 124, 13554 (2002).
  • 12. Smirnov S.N., Golubev N.S., Denisov G.S., Benedict H., Schah-Mohammedi P. and Limbach H.H., J. Am. Chem. Soc., 118,4094 (1996); Smirnov S.N., Benedict H., Golubev N.S., Denisov G.S., Kreevo M.M., Schowen R.L. and Limbach H.-H., Canad. J. Chem., 77,943 (1999); Shenderovich I.G., Burtse A.P., Denisov G.S., Golubev N.S. and Limbach H.-H., Magn. Reson. Chem., 39, S91-S99 (2001 Shenderovich I.G., Limbach H.-H., Smirnov S.N., Tolstoy P.M., Denisov G.S. and Golubev N.S., Phy Chem. Chem. Phys., 4, 5488 (2002).
  • 13. Jencks W.P. and Regenstein J., in Handbook of Biochemistry, 2 ed., Chemical Rubber Co., Clevelan OH, 1970, p. J-216f.
  • 14. Denisov G.S., Gindin V.A., Golubev N.S., Ligay S.S., Shchepkin D.N. and Smirnov S.N., J. Mol. Lit 67,217(1995).
  • 15. Sobczyk L. and Pawełka Z.,J. Chem. Soc., Farad. Trans. 1,70,832 (1974); Brycki B., Dega-Szafran and Szafran M., Adv. Mol. Relax. Ini. Proc., IS, 71 (1979); Dega-Szafran Z., Szafran M., Stefaniak I Brevard C. and Bourdonneau M., Magn. Reson. Chem., 24, 424 (1986).
  • 16. Saunders M., Telkowski L. and Kates M.R.,7. Am. Chem. Soc., 99, 8070(1977); Siehl H.-U., Adv. Ph Org. Chem., 23, 63 (1987); Forsyth D.A., In Isotopes in Organic Chemistry; Eds. Buncel E. and L C. C., Elsevier, Amsterdam, 1987, Vol. 6, Chapter 1.
  • 17. Schah-Mohammedi P., Shenderovich I.G., Detering C., Limbach H.-H., Tolstoy P.M., Smirnov S.l Denisov G.S. and GolubevN.S., J. Am. Chem. Soc., 122,12878 (2000); DziembowskaT., Rozwadow: Z., Filarowski A. and Hansen, P.E., Magn. Reson. Chem., 39, S67 (2001); Grech E., Klimkiewicz Nowicka-Scheibe J., Pietrzak M., Schilf W., Pozharski A.F., Ozeryanski V.A., Bolvig S., Abildgaarc and Hansen P.E., J. Mol. Struct., 615, 121 (2002).
  • 18. Batiz-Hemandez H. and Bemheim R.A., Prog. Nucl. Magn. Reson. Spectrosc., 3, 63 (1967); Han: P.E., Annu. Rep. NMR Spectrosc., 15,105 (1983); Hansen P.E., Prog. Nucl. Magn. Reson. Spectrosc., 207 (1988); Hansen P.E., Magn. Reson. Chem., 38, 1 (2000).
  • 19. Ellison S.L.R. and Robinson M.J.T., J. Chem. Soc., Chem. Commun., 745 (1983); Tanaka N. and Ar M., J. Am. Chem. Soc., 107, 7780 (1985).
  • 20. Benedict H., Limbach H.-H., Wehlan M., Fehlhammer W.-P., Golubev N.S. and Janoschek R., J. Am. Chem. Soc., 120, 2939(1998).
  • 21. Barczynski P., Dega-Szafran Z. and Szafran M., J. Chem. Soc., Perkin Trans. 2, 901 (1987); Dega-Szafran Z., Dulewicz E. and Szafran M., J. Mol. Struct., 177, 317 (1988).
  • 22. Rospcnk M., Sobczyk L., Schah-Mohammedi P., Limbach H.-H., Golubev N.S. and Melikova S. Magn. Reson. Chem., 39, S81 (2001).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0022-0033
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