The C-13 chemical shift dependences of phenol on pH have been investigated and the shifts interpreted in terms of the phenol-phenoxide equilibrium and hydrogen bonding. In the low and high ranges of pH the carbon shifts have been related to subtle changes in the characteristics of solvent properties. The spectra were obtained using the Fourier transform technique.
MacielG. E. and JamesR. V., J. Amer. Chem. Soc.86, 3893 (1964).
2.
LauterburP. C., J. Amer. Chem. Soc.83, 1846 (1961).
3.
The essential invariance of the 13C shieldings over this pH range constitutes strong evidence that there is no significant protonation of phenol even at the lowest pH's included in this study.
4.
SpieseckeH. and SchneiderW. G., J. Chem. Phys.33, 731 (1961).
5.
PopleJ. A.BeveridgeD. L., and DoboshP. A., J. Chem. Phys.47, 2026 (1967).
