Abstract
The work reported here is the result of an experimental calo-rimetric investigation of a series of intermolecular complexes which fall into the category labeled “charge transfer” complexes (1–5) or “donor-acceptor” complexes (4). Specifically, the systems studied consist of two compounds which are postulated to have an electron donor-acceptor relationship to one another (1). The donor molecules used were benzene, the methyl substituted benzenes, thianthrene, naphthalene, acenaphthalene, phenanthrene, and pyrene. The acceptor molecules were tetracyanoethylene (TCNE), 1,3,5-trinitrobenzene (TNB), and picric acid (1,3,5-trinitrophenol or PA). The calorimetric experiments were carried out in methylene chloride solution, all possible donor-acceptor combinations were used, and a 1:1 acceptor to donor complex constitution was assumed. These calorimetric investigations are the first studies of this type.
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References
Mulliken, R.S. and Person, W.B., “Molecular Complexes,” Wiley-Interscience, New York (1969).
Andrews, L.J. and Keefer, R.M., “Molecular Complexes in Organic Chemistry,” Holden-Day, New York (1964).
Rose, J., “Molecular Complexes,” Peragon Press, New York (1967).
Briegleb, G., “Electronen-Donator Complexe,” Springer-Verlog, New York (1961).
Foster, R., “Organic Charge Transfer Complexes,” Academic Press, New York (1969).
Bentley, M.D. and Dewar, J.J.S., Tetrahedron Lett., 50, 5043 (1967).
Benesi, H.A. and Hildebrand, J.H., J. Amer. Chem. Soc., 70, 2382 (1948);
Benesi, H.A. and Hildebrand, J.H., J. Amer. Chem. Soc.,71, 2703 (1949).
Mulliken, R.S., J. Amer. Chem. Soc, 72, 600 (1950).
Mulliken, R.S., J. Amer. Chem. Soc., 74, 811 (1952).
Mulliken, R.S., J. Phys. Chem. 56, 801 (1952).
Mulliken, R.S. and Reid, C., J. Amer. Chem. Soc, 76, 3869 (1954).
Mulliken, R.S., Reciul, 75, 845 (1956).
Orgel, L.E. and Mulliken, R.S., J. Amer. Chem. Soc, 79, 4839 (1957).
Murrell, J.N., J. Amer. Chem. Soc, 81, 5037 (1959).
Subomaira, H.T. and Mulliken, R.S., J. Amer. Chem. Soc, 82 5966 (1960).
Mulliken, R.S. and Person, W.B., Ann. Rev. Phys. Chem., 13, 107 (1962).
Murrell, J.N., Quart. Rev., 15, 191 (1961).
Lepley, A.R., J. Amer. Chem. Soc, 86 2545 (1964).
Dewar, J.J.S. and Thompson, C.C., Tetrahedron Suppl., 7, 97 (1966).
Carter, S., Murrell, J.N., and Rosch, E.J., J. Chem. Soc. (London), 2048 (1965).
Johnson, G.D. and Bowen, R.E., J. Amer. Chem. Soc, 87, 1655 (1965).
Dewar, J.J.S. and Lepley, A.R. , J. Amer. Chem. Soc, 83, 4560 (1961).
Lepley, A.R., J. Amer. Chem. Soc, 84, 3577 (1962).
McConnel, H., Ham, J.S., and Platt, J.R., J. Chem. Phys., 21, 66 (1953).
Foster, R., Tetrahedron, 10, 95 (1960).
Andrews, L.J. and Keefer, R.M., J. Amer. Chem. Soc, 73, 4169 (1951).
Scott, R.L., Recuil, 75, 787 (1956).
Ketelaar, J.A.A., van de Stolpe, C., Goudsmit, A., and Dzcubas, W., Recuil, 71, 1104 (1952).
de Maine, P.A.D. and Seawaight, R.D., Ind. Eng. Chem., 55, 29 (1963).
de Maine, P.A.D., Spectroschim. Acta, 15, 1051 (1959).
Foster, R., Hammick, D.L., and Wardley, A.A., J. Chem. Soc. (London), 3817 (1953).
Nagakura, S., J. Amer. Chem. Soc, 80, 520 (1958).
Rose, N.J. and Drago, R.S., J. Amer. Chem. Soc, 81, 6138 (1959).
Merrifield, R.E. and Phillips, W.D., J. Amer. Chem. Soc, 80, 2778 (1958).
Weissberger, A., “Physical Methods of Organic Chemistry,” Vol. I, Part I, Interscience, New York (1959).
Skinner, H.A., “Experimental Thermochemistry,” Interscience, New York (1962).
Christensen, J.J., Izatt, R.M., Hansen, L.D., and Partridge J.A., J. Phys. Chem., 70, 2003 (1966).
Izatt, R.M., Eatough, D., and Christensen, J.J., J. Phys. Chem., 72 2720 (1968).
Gol’clstein, I.P., Gur’yanova, E.N., and Karpovich, I.R., Russian J. Chem., 39, 491 (1965).
Jordan, J. and Alleman, T.G., Anal. Chem., 29, 9 (1957).
Bolles, T.F. and Drago, R.S., J. Amer. Chem. Soc, 87, 5015 (1965).
Olofsson, G., Acta Chim. Scandanavia, 20, 2289 (1966).
Epley, T.D. and Drago, R.S., J. Amer. Chem. Soc., 89, 5770 (1967).
Nelander, B., Acta Chim. Scand., 20, 2289 (1966).
Gill, S.J. and Forquhar, E.L., J. Amer. Chem. Soc, 90, 3039 (1968).
Izatt, R.M., Eatough, D., Snow, R.L., and Christensen, J.J., J. Phys. Chem. 72, 1208 (1968).
Christensen, J.J., Wrathall, D.P., Izatt, R.M. , and Tolman, D.O., J. Phys. Chem., 71., 3001 (1967).
Christensen, J.J., Wrathall, D.P., and Izatt, R.M., Anal. Chem., 40, 175 (1968).
Sillen, L.G., Acta Chim. Scand., 16, 159 (1962).
Pasletti, P., Vacca, A., and Arenare, D., J. Phys. Chem., 70, 193 (1966).
Somen, G., Coops, Y., and Tolk, M.W., Recuil, 82, 231 (1963).
Wagner, W., Zeischrift für Physical Chemistry, 218, 392 (1961).
Wadso, I., Science Tools, 13, 33 (1966).
Vandersee, CE. and Swanson, J.S., J. Phys. Chem., 67, 208 (1963).
Hale, J.P., Izatt, R.M., and Christensen, J.J., J. Phys. Chem., 67, 2605 (1963).
Gunn, S.R., J. Phys. Chem., 69, 2920 (1965).
Everett, D.H. and Wynne-Jones, W.F.K., Trans. Faraday Soc, 35, 1380 (1939).
Harned, H.S. and Robinson, R.A., Trans. Faraday Soc., 36, 973 (1940).
Fieser, L.F. and Fieser, M., “Reagents in Organic Synthesis,” Wiley, New York (1967).
“Handbook of Chemistry and Physics,” Chemical Rubber Company, 50th edition (1969).
Herndon, W.C. and Goodin, R.D., J. Phys. Chem., 73, 2793 (1969).
Roseinsky, D.R. and Kellaivi, H., J. Chem. Soc. (London), 1207 (1969).
Thompson, C.C. and de Maine, P.A.C., J. Phys. Chem., 69, 2766 (1965).
Jureniki, N.B. and de Maine, P.A.D., J. Amer. Chem. Soc, 86, 3217 (1964).
Prue, J.E., J. Chem. Soc. (London), 7534 (1965).
Person, W.B., J. Amer. Chem. Soc, 87, 167 (1965).
Emslie, P.H., Foster, R., Fyfe, C.A., and Norman, I., Tetrahedron, 21, 2843 (1965).
Hammond, P.R., J. Chem. Soc. (London), 481 (1964).
Foster, R. and Horman, I., J. Chem. Soc. (B) (London), 171 (1966).
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Herndon, W.C., Feuer, J., Mitchell, R.E. (1974). Calorimetric Studies of Pi-Molecular Complexes. In: Porter, R.S., Johnson, J.F. (eds) Analytical Calorimetry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-4509-2_20
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