C13 Nuclear Magnetic Resonance Spectroscopy. IV. Aniline, N,N-Dimethylaniline, and Their Methyl Derivatives: Steric Inhibition of Conjugation
- 15 March 1963
- journal article
- Published by AIP Publishing in The Journal of Chemical Physics
- Vol. 38 (6) , 1415-1431
- https://doi.org/10.1063/1.1733866
Abstract
The C13nuclear magnetic resonance spectra of aniline, nine methylanilines, N,N‐dimethylaniline and eight methyl‐N,N‐dimethylanilines have been obtained and analyzed. A detailed study of the influence of methyl substituents on ring carbon shieldings has been made, and estimates of the changes in charge distributions resulting from steric inhibition of conjugation derived from the results. Reasonably good agreement with other theoretical and experimental investigations of these effects has been found. The N‐methyl carbon shieldings appear to be correlated with the base strengths of the amines.Keywords
This publication has 27 references indexed in Scilit:
- Proton Exchange in Carbonium Ions of Methyl-Substituted BenzenesThe Journal of Chemical Physics, 1961
- Chemical Shifts in C5H5-, C6H6 and C7H7+; Chemical Shifts and π-Electron Densities1Journal of the American Chemical Society, 1960
- Electronic Structure and Spectrum of AcetanilideThe Journal of Chemical Physics, 1960
- SOLVENT EFFECTS ON MESOMERIC CHARGE SEPARATION1Journal of the American Chemical Society, 1960
- Steric effects on mesomerism. XVII. Some properties of aromatic nitro‐, amino‐, and acylamino compounds with bulky ortho‐substituentsRecueil des Travaux Chimiques des Pays-Bas, 1958
- Steric effects on mesomerism. XVI). Comparative investigations involving ultra‐violet absorption spectra, molecular refractions, rates of reaction, and basic strengths of aromatic aminesRecueil des Travaux Chimiques des Pays-Bas, 1957
- Homomorphs of 2,6-Dimethyl-t-butylbenzene1,2Journal of the American Chemical Society, 1953
- Steric effects on mesomerism IX : The basic strength of benzoquinuclidine and its bearing on the basic strength and the mesomeric energy of aromatic aminesRecueil des Travaux Chimiques des Pays-Bas, 1952
- Geometry and Spectra of Substituted AnilinesJournal of the American Chemical Society, 1949
- The Effects of Steric Inhibition of Resonance on Ultraviolet Absorption Spectra1Journal of the American Chemical Society, 1945