Substituent effects on the benzene ring. Prediction of the thermochemical properties of alkyl substituted hydroquinones

Abstract

The standard molar enthalpies of formation Δ_fH_m^°(cr) at 298.15 K for hydroquinone, 2-methylhydroquinone, 2-tert-butylhydroquinone, 2,5-di-tert-butylhydroquinone, and 2,3-dicyanohydroquinone were measured by combustion calorimetry. The standard molar enthalpies of sublimation of 2-methylhydroquinone, 2-tert-butylhydroquinone, and 2,5-di-tert-butylhydroquinone were obtained from the temperature dependence of the vapour pressure measured in a flow system. Molar enthalpies of fusion Δ_cr^lH_m^° of the latter compounds were measured by differential scanning calorimetry (DSC). Resulting values of Δ_fH_m^°(g) were obtained at 298.15 K and were used to derive the strain enthalpies of alkylhydroquinones. The intramolecular interactions of the substituents are discussed in terms of the deviations of Δ_fH_m^°(g) from the group additivity rules. No peculiarities in the interaction energies among the alkyl and the hydroxy groups in the ortho- and meta-positions of alkylhydroquinones were detected in comparison with alkyl-substituted phenols. Thus, no new parameters are needed for the prediction of the Δ_fH_m^°(g) of similar shaped alkylhydroquinones by using the group-additive procedure.

References

1. R. Bender, V. Bieling and G. Mauer, J. Chem. Thermodyn., 1983, 15, 585.
2. C. G. DeKruif, E. J. Smit and H. A. Gover, J. Chem. Phys., 1981, 74, 5838.
3. S. Seki and K. Susuki, Bull. Chem. Soc. Jpn, 1953, 26, 206.
4. A. Magnus, Z. Phys. Chem. (Frankfurt), 1956, 9, 141.
5. J. P. Pedley, R. D. Naylor and S. P. Kirby, Thermochemical Data of Organic Compounds, Chapman and Hall, London, 2nd edn., 1986.
6. R. Sabbah and E. N. L. E. Buluku, Can. J. Chem., 1991, 69, 481.
7. G. S. Parks, K. E. Manchester and L. M. Vaughan, J. Chem. Phys., 1954, 22, 2089.
8. G. Pilcher and L. E. Sutton, J. Chem. Soc., 1956, 2695.
9. D. H. Andrews, G. Lynn and J. Johnston, J. Am. Chem. Soc., 1926, 48, 1274.
10. P. Bret-Dibat and A. Lichanot, Thermochim. Acta, 1989, 147, 261.
11. W. F. Hemminger and H. K. Cammenga, Methoden der Thermischen Analyse, Springer, Berlin, 1989, p. 269.
12. H.-D. Beckhaus, G. Kratt, K. Lay, J. Geiselmann, C. Rüchardt, B. Kitschke and H. J. Lindner, Chem. Ber., 1980, 113, 3441.
13. S. P. Verevkin, H.-D. Beckhaus and C. Rüchardt, Thermochim. Acta, 1992, 197, 27.
14. CODATA Key Values for Thermodynamics, ed. J. D. Cox, D. D. Wagman and V. A. Medvedev, Hemisphere, New York, 1989.
15. J. D. Cox and G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic Press, London, New York, 1970.
16. J. S. Chickos, D. G. Hesse, S. Y. Panshin, D. W. Rogers, M. Saunders, P. M. Uffer and J. F. Liebman, J. Org. Chem., 1992, 57, 1897.
17. W. N. Hubbard, D. W. Scott and G. Waddington, in Experimental Thermochemistry, ed. F. D. Rossini, Interscience, 1956, p. 75.
18. J. S. Chickos and R. Annunziata, J. Org. Chem., 1986, 51, 4311.
19. K. Rakus, S. P. Verevkin, H. D. Beckhaus and C. Rüchardt, Chem. Ber., 1994, 127, 1095.
20. M. H. Charlton, R. Docherty and M. G. Hutchings, J. Chem. Soc., Faraday Trans., 1995, 2023.
21. T. Sato-Toshima, M. Sakiyama and S. Seki, Bull. Chem. Soc. Jpn., 1980, 53, 2762.
22. H. Y. Afeefy, J. F. Liebman and S. E. Stein, Neutral Thermochemical Data in NIST Standard Reference Database Number 69, ed. W. G. Mallard and P. J. Linstrom, National Institute of Standards and Technology, Gaithersburg MD, 20899. March 1998, (http://webbook.nist.gov).
23. S. P. Verevkin, J. Chem. Thermodyn., 1998, 30 in press.
24. W. V. Steele, R. D. Chirico, S. E. Knipmeyer and A. Nguyen, J. Chem. Eng. Data, 1997, 42, 1008.
25. W. V. Steele, R. D. Chirico, S. E. Knipmeyer and A. Nguyen, J. Chem. Eng. Data, 1997, 42, 1021.
26. A. von Bayer, Chem. Ber., 1885, 98, 297.
27. J. F. Liebman and A. Greenberg, Strained Organic Molecules, Organic Chemistry Series 38, Academic Press, New York, 1978.
28. S. W. Benson, Thermochemical Kinetics, Wiley, New York, 1976.
29. N. Cohen, J. Phys. Chem. Ref. Data, 1996, 25, 1411.
30. P. von R. Schleyer, J. E. Williams and K. P. Blanchard, J. Am. Chem. Soc., 1970, 92, 2377.
31. H.-D. Beckhaus, Chem. Ber., 1983, 116, 86.
32. D. Zavoianu, I. Ciocazanu, S. Moga-Gheorghe and C. Bornaz, Rev. Chim. (Bucharest), 1988, 39, 487.
33. S. P. Verevkin, Ber. Bunsen Ges. Phys. Chem., 1998, 102, 1467.
34. S. P. Verevkin, J. Chem. Thermodyn., 1998, 30, 389.
35. S. P. Verevkin, J. Chem. Thermodyn., 1998, 30, 1029.