Proton, carbon, and nitrogen-14 nuclear magnetic resonance studies are reported of hydrogen bonding between the OH proton of o-phenylphenol (OPP) and the nitrogen electron donor of pyridine (Py). Data are also reported on the hydrogen bonding of the acid and base components of coal-derived asphaltenes with the model system. Determination was made of the equilibrium constant of the 1:1 complex between OPP and Py from the proton NMR studies. Qualitative results are reported from the 13C and 14N studies of the model system (OPP-Py) with the individual asphaltene fractions. Because of the recent renewed interest in coal liquefaction this investigation may provide a starting point for future research.
WellerS.PelipetzM. G., and FriedmanS., Ind. Eng. Chem.43, 1572 (1951).
2.
WellerS.PelipetzM. G., and FriedmanS., Ind. Eng. Chem.43, 1575 (1951).
3.
PelipetzM.KuhnE. M.FriedmanS., and StorchH. H., Ind. Eng. Chem.40, 1259 (1948).
4.
SternbergH. W.RaymondR., and SchweighardtF. K., Science188, 49 (1975).
5.
GivenP. H., Fuel33, 147 (1960).
6.
AkhtarS.MazzoccoN. J.WeintraubM., and YavorakyP. M., Paper presented at the 4th Synthetic Fuels from Coal Conference, Oklahoma State University, Stillwater, 6–7 May, 1974.
7.
HalleuxA. and TschamlerH., Fuel49, 291 (1959).
8.
DeardenJ. C. and ForbesW. F., Can. J. Chem.38, 896 (1960).
9.
DadokJ.SprecherR. F.Bothner-ByA. A., and LinkT., Paper presented at the 11th Experimental NMR Conference, Pittsburgh, April 1970. (250 MHz NMR Spectrometer Facility is supported by Public Health Service Grant RR 00292.)
10.
DadokJ. and SprecherR. F., J. Mag. Resonance13, 243 (1974).
11.
SpieseckeH. and SchneiderW. G., J. Chem. Phys.35, 731 (1961).
12.
FraenkelG.CarterR. E.McLachlanA., and RichardsJ. H., J. Am. Chem. Soc.82, 5846 (1960).
13.
WangS. M. and LiN. C., J. Am. Chem. Soc.88, 4592 (1966).
14.
SaitoH. and NukadaK., Tetrahedron Letters, 111 (1965).
15.
EvansD. F., J. Chem. Soc.5575 (1963).
16.
JoestenM. D. and SchaadL. J., Hydrogen Bonding (Dekker, New York, 1974).
17.
WangS. M. and LiN. C., J. Am. Chem. Soc.90, 5069 (1968).
18.
TakahashiF. and LiN. C., J. Phys. Chem.69, 1622 (1965).
19.
SchweighardtF. K.MollC., and LiN. C., J. Mag. Resonance2, 35 (1970).
20.
StillsonG. H.SawyerD. W., and HuntC. K., J. Am. Chem. Soc.67, 303 (1945).
21.
SomersB. G. and GutowskyH. S., J. Am. Chem. Soc.85, 3065 (1965).
22.
CohenL. A. and JonesW. M., J. Am. Chem. Soc.85, 3404 (1965).
23.
SchweighardtF. K.RetcofskyH. L., and FriedelR. A., Fuel, in press.
24.
StrothersJ. B., Carbon-13 NMR Spectroscopy (Academic Press, New York, 1972), Organic Chemistry, Vol. 24, p. 197.
25.
LevyG. C. and NelsonG. L., Carbon-13 Nuclear Magnetic Resonance for Organic Chemist (Wiley-Interscience, New York, 1972), p. 81.
26.
LarkindaleJ. P. and SimkinD. J., J. Chem. Phys.55, 5048 (1971).
27.
WitanowskiM. and WebbG. A., Nitrogen NMR (Plenum Press, London, 1973), p. 249.
28.
FriedelR. A. and QueiserJ. A., Anal. Chem.28, 22 (1956).
29.
OrchinM. and StorchH. H., Ind. Eng. Chem.40, 1385 (1948).
30.
SternbergH. W.RaymondR., and AkhtarS., Paper presented at the American Chemical Society Meeting, Philadelphia, 6–11 April 1975.
31.
PimentelG. C. and McClellanA. L., The Hydrogen Bond (Freeman, San Francisco, 1960).
