This study represents an integrated approach towards understanding the electronic and structural aspects of 2-benzylamino-1,4-naphthalenedione, a representative 2-amino-napfthoquinone. To this end, theoretical calculations performed at the B3PW91/6-31+G(d) level of density functional theory, electrochemical and X-ray structural investigation were employed. Two intramolecular H-bonds and other two intermolecular H-bonds were observed, including non-classical interactions. Cyclic voltammogram (CV) and differential pulse voltammetry (DPV) show two pairs of peaks, being each one a monoelectronic process.

The importance of hydration on the equilibrium involving internal rotation around carbon-carbon single bond is investigated for the furfural molecule dissolved in water. To analyze the solvent effects in stabilizing any preferred conformation of furfural, we perform Monte Carlo (MC) NPT simulations corresponding to different rotation angles of the carbonyl group. The hydrogen bonds formed between solute and solvent are also analyzed along the conformational equilibrium. They are found to be equivalent, both in number and in binding energy, for all rotation angles. These results give a strong evidence that the conformational stability and the rotation barrier of the furfural molecule in water relate to the bulk properties rater than solute-solvent hydrogen bonds.