Effect of the metal ion and the medium on the electronic structure of anthranilic acid: a modelling study on the Li and the BeH derivatives

Abstract

This computational organic chemistry study illustrates that the size of the metal ion is a critical point in determining the bonding mode of the anthranilate (2-aminobenzoate). The beryllium model structure is the first example in the chemical literature on the ability of this amino acid to bond as N–O chelate. The medium has variable effect on the energies and the dipole moments of the studied models, which was found originating essentially from the differences in the atomic charges of the metals. Analysis of the molecular charge distribution allowed stating a new theory on the effect of the medium on the two pairs of isomers.

Keywords:

• anthranilic acid
• solvent effect
• dipole moment
• natural population analysis charges

Acknowledgement

We thank Al-Hussein Bin Talal University for supporting this research through the research grant 2008/78.