Thermochemical and theoretical studies of 4-methylbiphenyl, 4,4′-dimethylbiphenyl, 4,4′-dimethyl-2,2′-bipyridine

Abstract

The standard (p°=0.1 MPa) molar enthalpies of formation for 4-methylbiphenyl, 4,4′-dimethylbiphenyl and 4,4′-dimethyl-2,2′-bipyridine were derived from the standard molar enthalpies of combustion, in oxygen, at T=298.15 K, measured by static-bomb combustion calorimetry. The standard molar enthalpies of sublimation, at T=298.15 K, were measured by Calvet microcalorimetry. Theoretical calculations at the ab initio restricted Hartree–Fock (RHF) level with second-order Møller–Plesset (MP2) perturbation theory correlation corrections and density functional theory (DFT) have been carried out for all these molecules in order to access their stabilitites relative to the non-substituted ones. The theoretical results are in general good agreement with the experimental results.

References

1. M. A. V. Ribeiro da Silva, V. M. F. Morais, M. A. R. Matos and C. M. A. Rio, J. Org. Chem., 1995, 60, 5291.
2. M. A. V. Ribeiro da Silva, M. D. M. C. Ribeiro da Silva and G. Pilcher, Rev. Port. Quim., 1984, 26, 163.
3. M. A. V. Ribeiro da Silva, M. D. M. C. Ribeiro da Silva and G. Pilcher, J. Chem. Thermodyn., 1984, 16, 1149.
4. M. A. V. Ribeiro da Silva, M. L. C. H. Ferrão and A. M. R. O. A. Silva, J. Chem. Thermodyn., 1995, 27, 633.
5. W. N. Hubbard, D. W. Scott and G. Waddington, in Experimental Thermochemistry, ed. F. D. Rossini, Interscience, New York, 1956, vol. 1, ch. 5.
6. The NBS Tables of Chemical Thermodynamic Properties, J. Phys. Chem. Ref. Data, 1982, 11, suppl. no. 2.
7. Handbook of Chemistry and Physics, ed. R. C. Weast, 70th edn., CRC Press, Boca Raton, FL, 1989.
8. IUPAC, J. Phys. Chem. Ref. Data, 1993, 22, 1571.
9. F. A. Adedeji, D. L. S. Brown, J. A. Connor, M. Leung, M. I. Paz-Andrade and H. A. Skinner, J. Organomet. Chem., 1975, 97, 221.
10. D. R. Stull, E. F. Westrum and G. C. Sinke, The Chemical Thermodynamics of Organic Compounds, Wiley, New York, 1969.
11. F. D. Rossini, Experimental Thermochemistry, ed. F. D. Rossini, Interscience, New York, 1956, vol. 1, ch. 14.
12. CODATA, J. Chem. Thermodyn., 1978, 10, 903.
13. M. Dupuis, D. Spangler and J. J. Wendoloski, NRCC Software Catalog, University of California, Berkeley, CF, 1980, vol. 1, Program QG01.
14. M. W. Schmidt, J. A. Boatz, K. K. Baldridge, S. Koseki, M. S. Gordon, S. T. Elbert and B. Lam, Quantum Chemistry Program Exchange Bull., 1987, 7, 115.
15. P. C. Hariharan and J. A. Pople, Chem. Phys. Lett., 1972, 66, 217.
16. M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees and J. A. Pople, J. Chem. Phys., 1982, 77, 3645.
17. J. S. Binkley, J. A. Pople and W. J. Hehre, J. Am. Chem. Soc., 1980, 102, 939.
18. M. S. Gordon, J. S. Binkley, J. A. Pople, W. J. Pietro and W. J. Hehre, J. Am. Chem. Soc., 1982, 104, 2797.
19. A. St-Amant, PhD Thesis, 1992, Université de Montréal.
20. A. D. Becke, Phys. Rev. A: Gen. Phys., 1988, 38, 3098.
21. J. P. Perdew, Phys. Rev. B: Condens. Matter, 1986, 33, 8822.
22. W. J. Hehre, R. Ditchfield, R. Radom and J. A. Pople, J. Am. Chem. Soc., 1970, 92, 4796.
23. A. Almeningen, O. Bastiansen, L. Fernholt, B. N. Cyvin and S. Samdal, J. Mol. Struct., 1985, 128, 59.
24. J. P. Foster and F. Weinhold, J. Am. Chem. Soc., 1980, 102, 115.
25. A. E. Reed and F. Weinhold, J. Chem. Phys., 1983, 78, 4066.