Nuclear Magnetic Resonance in Amino-group of Aniline Derivatives
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概要
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Concentration dependence of the chemical shift of amino protons in aniline derivatives in carban tetrachloride and acetone solutions were measured. The chemical shift of the amino proton in aniline derivatives is revealed to be clearly dependent on the existence of the ortho-methyl group. In carbon tetrachloride solutions, the concentration dependence of the resonance lines is slight, suggesting that the association of the solute molecules by hydrogen bonding is very weak. In acetone solutions, the dependence suggests hydrogen bond formation between solute and acetone. The base strength of aniline derivatives appeared to have no direct correlation with the magnitude of the chemical shift of amino proton in these compounds. The ring proton spectra of dimethyl aniline are slightly concentration dependent. The resonance in the ortho-protons appers to be displaced to a lower field on dilution and this tendency was ascribed to the change in the electrostatic field at the proton arising from the N–H bond moment change by hydrogen bond formation.
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