We located ‘hidden’ S-character chirality in formally achiral glycine using a vector-based interpretation of the total electronic charge density distribution. We induced the formation of stereoisomers in glycine by the application of an electric field. Control of chirality was indicated from the proportionate response to a non-structurally distorting electric field. The bond-flexing was determined to be a measure of bond strain, which could be a factor of three lower or higher, depending on the direction of the electric field, than in the absence of the electric field. The bond-anharmonicity was found to be approximately independent of the electric field. We also compared the formally achiral glycine with the chiral molecules alanine and lactic acid, quantifying the preferences for the S and R stereoisomers. The proportional response of the chiral discrimination to the magnitude and direction of the applied electric field indicated use of the chirality discrimination as a molecular similarity measure.

We seek to explain why the hydrogen bond possesses unusual strength in small water clusters that account for many of the complex behaviors of water. We have investigated and visualized the donation of covalent character from covalent (sigma) to hydrogen-bonds, by calculating the eigenvector coupling properties of QTAIM, stress tensor σ(r) and Ehrenfest Force F(r) on the F(r) molecular graph. The next generation 3-D bond-path framework sets are presented and only the F(r) bond-path framework sets reproduce the earlier finding on the coupling between covalent (sigma) and hydrogen-bonds that possess a degree of covalent character. The directional character of the covalent (sigma) and hydrogen-bonds 3-D bond-path framework sets for the F(r) explains differences found in the earlier results from QTAIM and the stress tensor σ(r).