Abstract
The thermodynamic parameters of reactions of phenyl isocyanate with methanol monomer, dimer, and trimer were calculated by the B3LYP and MP2 quantum-chemical methods. The enthalpies and entropies of transformations were found to increase as the degree of methanol association grew. An isokinetic dependence was observed for the transformations under consideration. The influence of the polarity of solvents on the Gibbs energies of these reactions was estimated.
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References
J. H. Saunders and K. C. Frisch, Polyurethanes: Chemistry and Technology, Part 1: Chemistry (Interscience, New York, 1962–1964; Khimiya, Moscow, 1968).
E. G. Lovering and K. J. Laider, Can. J. Chem. 40(1), 26 (1962).
M. C. Pannone and Ch. W. Macosko, J. Appl. Polym. Sci. 34(7), 2409 (1987).
W. Sultan and J. P. Busnel, J. Therm. Anal. Calorimetry 83(2), 355 (2006).
W. P. Yang, Ch. W. Macosco, and S. T. Wellinghoff, Polymer 27(8), 1235 (1986).
D. Joel and A. Hauser, Angew. Makromol. Chem. 217, 191 (1994).
Ch. Steinlein, L. Harnandez, and C. D. Eisenbach, Macromol. Chem. Phys. 197(10), 3365 (1996).
Q.-W. Lu, T. R. Hoye, and Ch. W. Macosko, J. Polym. Sci., Part A: Polym. Chem. 40(14), 2310 (2002).
N. J. Daly and F. Ziolkowski, J. Chem. Kinetics 12(4), 241 (1980).
A. E. Oberth and R. S. Bruenner, J. Am. Chem. Soc. 72(3), 845 (1968).
S. G. Entelis and R. P. Tiger, Reaction Kinetics in the Liquid Phase (Khimiya, Moscow, 1973; Wiley, New York, 1976).
S. P. Bondarenko, R. P. Tiger, and S. G. Entelis, Zh. Fiz. Khim. 55(7), 1716 (1981).
P. A. Berlin, S. P. Bondarenko, R. P. Tiger, and S. G. Entelis, Khim. Fiz. 3(5), 722 (1984).
P. A. Berlin, R. P. Tiger, Yu. N. Chirkov, and S. G. Entelis, Khim. Fiz. 3(10), 1448 (1984).
P. A. Berlin, R. P. Tiger, and S. G. Entelis, Kinet. Katal. 28(6), 1347 (1987).
G. Raspoet, M. T. Nguen, M. McGarraghy, and A. F. Hegarty, J. Org. Chem. 63(20), 6878 (1998).
O. Mo, M. Yanez, and J. Elguero, J. Chem. Phys. 107(9), 3592 (1997).
R. W. Larsen and M. A. Suhm, J. Chem. Phys. 125(15), 154314 (2006).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 03, Revision B.04 (Gaussian Inc., Pittsburg, PA, 2003).
A. A. C. C. Pais, A. Sousa, M. E. Eusebio, and J. S. Redinha, Phys. Chem. Chem. Phys. 3(18), 4001 (2001).
M. Frenkel, G. J. Kabo, K. N. Marsh, et al., Thermodynamics of Organic Compounds in the Gas State (Thermodynamics Research Center, College Station, TX, 1994).
K.-M. Marstokk and H. Mollendal, Acta Chem. Scand. 53(3), 79 (1999).
A. L. Moraczewski, L. A. Banaszynski, A. M. From, et al., J. Org. Chem. 63(21), 7258 (1998).
Yu. G. Bushuev and T. A. Dubinkina, Zh. Fiz. Khim. 70(9), 1628 (1996) [Russ. J. Phys. Chem. 70 (9), 1512 (1996)].
Yu. G. Bushuev, Doctoral Dissertation in Chemistry (Ivanovo State Univ. of Chemical Technology, Ivanovo, 2001).
O. A. Osipov, V. I. Minkin, and A. D. Garnovskii, Handbook of Dipole Moments, 3rd ed. (Vysshaya Shkola, Moscow, 1971) [in Russian].
W. Weltner and K. S. Pitzer, J. Am. Chem. Soc. 73(6), 2606 (1951).
R. A. Alberty, M. B. Chung, and T. M. Flood, J. Phys. Chem. Ref. Data 16(3), 391 (1987).
K. Ya. Burshtein and P. P. Shorygin, Quantum-Chemical Calculations in Organic Chemistry and Molecular Spectroscopy (Nauka, Moscow, 1989) [in Russian].
L. A. Curtiss and M. Blander, Chem. Rev. 88(6), 827 (1988).
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Original Russian Text © A.Ya. Samuilov, L.A. Zenitova, Ya.A. Levin, A.I. Kurdyukov, Ya.D. Samuilov, 2008, published in Zhurnal Fizicheskoi Khimii, 2008, Vol. 82, No. 12, pp. 2224–2229.
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Samuilov, A.Y., Zenitova, L.A., Levin, Y.A. et al. The thermodynamic parameters of reactions of phenyl isocyanate with methanol associates. Russ. J. Phys. Chem. 82, 1999–2004 (2008). https://doi.org/10.1134/S0036024408120042
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DOI: https://doi.org/10.1134/S0036024408120042