Prototropic equilibrium in complexes of N-methylmorpholine betaine with phenols studied by NMR and UV spectroscopy
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Add time:07/17/2019 Source:sciencedirect.com
Fourteen complexes of N-methylmorpholine betaine (MMBet) with phenols (pKa from 9.99 to 0.33) are synthesized and analysed by 1H and 13C NMR in DMSO-d6 and UV–Vis spectroscopy in CH2Cl2, CH3CN and DMSO. The UV spectra of complexes with medium-strong phenols show separate absorptions for A–H⋯B and A−⋯HB+ species. The prototropic equilibrium is also confirmed by sigmoidal plots of proton and carbon chemical shifts of the N+CH2 group versus pKa values of phenols. The effects of solvent polarity and excess of base on an acid–base equilibrium are discussed.
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