The Conformation and Charge Distribution in the Hydrogen Bonded Chelate Ring of Mannich Bases
- 1 January 1983
- journal article
- research article
- Published by Wiley in Bulletin des Sociétés Chimiques Belges
- Vol. 92 (4) , 313-328
- https://doi.org/10.1002/bscb.19830920401
Abstract
The dipole moment of 17 Mannich bases has been measured for a broad range of the intramolecular hydrogen bond strength. The increase of the dipole moment caused by the hydrogen bond formation has been calculated and is discussed in terms of the proton transfer equilibrium.The conformation of the chelate ring was analyzed by means of the atom‐atom and Lippincott‐Schroeder potentials. The calculations predict a nonplanar structure for both the molecular hydrogen bonded form and the zwitterionic proton transfer form. The correlation between the chelate ring structure and the hydrogen bond strength is discussed.Keywords
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