Structure-Property Relationship in Selected Naphtho- and Anthra-Quinone Derivatives on the Basis of Density Functional Theory and Car–Parrinello Molecular Dynamics

Intra- and inter-molecular interactions were studied in 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone 1,4-dihydroxy-anthraquinone to shed more light on the molecular assembly phenomena. The electronic ground excited states features of compounds investigated find structure-property dependencies. theoretical study was carried out basis Density Functional Theory (DFT), its Time-Dependent (TD-DFT) extension, using Car–Parrinello Molecular Dynamics (CPMD). In order show how environmental effects modulate physico-chemical properties, simulations performed vacuo, with solvent reaction field (Polarizable Continuum Model (PCM) water as a solvent) crystalline phase. intramolecular hydrogen bonds bridged proton dynamics analyzed detail. aromatic rings structure changes estimated Harmonic Oscillator Aromaticity (HOMA) Atoms Molecules (AIM) theory. Symmetry-Adapted Perturbation (SAPT) employed for interaction energy decomposition dimers trimers. It found that presence polar decreased barrier transfer. However, it did not significantly affect aromaticity structure. SAPT results showed mutual polarization monomers dimer weak dispersion responsible most intermolecular attraction. seem be much weaker than bridges. TD-DFT confirmed excitations do play any significant role CPMD indicated protons are very labile Short transfer proton-sharing events observed, correlation between them twin bridges noticed, especially first compound.