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Article

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

1
Faculty of Chemistry, University of Wrocław, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland
2
Department of Fuels Chemistry and Technology, Wrocław University of Science and Technology, ul. Gdańska 7/9, 50-344 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Enrico Bodo
Symmetry 2021, 13(4), 564; https://doi.org/10.3390/sym13040564
Received: 8 March 2021 / Revised: 22 March 2021 / Accepted: 24 March 2021 / Published: 29 March 2021
Intra- and inter-molecular interactions were studied in 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone and 1,4-dihydroxy-anthraquinone to shed more light on the molecular assembly phenomena. The electronic ground and excited states features of the compounds were investigated to find structure-property dependencies. The theoretical study was carried out on the basis of Density Functional Theory (DFT), its Time-Dependent (TD-DFT) extension, and using Car–Parrinello Molecular Dynamics (CPMD). In order to show how the environmental effects modulate the physico-chemical properties, the simulations were performed in vacuo, with the solvent reaction field (Polarizable Continuum Model (PCM) and water as a solvent) and crystalline phase. The intramolecular hydrogen bonds and the bridged proton dynamics were analyzed in detail. The aromatic rings and electronic structure changes were estimated using the Harmonic Oscillator Model of Aromaticity (HOMA) and Atoms in Molecules (AIM) theory. The Symmetry-Adapted Perturbation Theory (SAPT) was employed for interaction energy decomposition in the studied dimers and trimers. It was found that the presence of a polar solvent decreased the energy barrier for the bridged proton transfer. However, it did not significantly affect the aromaticity and electronic structure. The SAPT results showed that the mutual polarization of the monomers in the dimer was weak and that the dispersion was responsible for most of the intermolecular attraction. The intermolecular hydrogen bonds seem to be much weaker than the intramolecular bridges. The TD-DFT results confirmed that the electronic excitations do not play any significant role in the intramolecular proton transfer. The CPMD results indicated that the protons are very labile in the hydrogen bridges. Short proton transfer and proton-sharing events were observed, and a correlation between them in the twin bridges was noticed, especially for the first investigated compound. View Full-Text
Keywords: naphthoquinone; anthraquinone; DFT; HOMA; AIM; SAPT; TD-DFT; CPMD naphthoquinone; anthraquinone; DFT; HOMA; AIM; SAPT; TD-DFT; CPMD
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MDPI and ACS Style

Kizior, B.; Panek, J.J.; Szyja, B.M.; Jezierska, A. Structure-Property Relationship in Selected Naphtho- and Anthra-Quinone Derivatives on the Basis of Density Functional Theory and Car–Parrinello Molecular Dynamics. Symmetry 2021, 13, 564. https://doi.org/10.3390/sym13040564

AMA Style

Kizior B, Panek JJ, Szyja BM, Jezierska A. Structure-Property Relationship in Selected Naphtho- and Anthra-Quinone Derivatives on the Basis of Density Functional Theory and Car–Parrinello Molecular Dynamics. Symmetry. 2021; 13(4):564. https://doi.org/10.3390/sym13040564

Chicago/Turabian Style

Kizior, Beata, Jarosław J. Panek, Bartłomiej M. Szyja, and Aneta Jezierska. 2021. "Structure-Property Relationship in Selected Naphtho- and Anthra-Quinone Derivatives on the Basis of Density Functional Theory and Car–Parrinello Molecular Dynamics" Symmetry 13, no. 4: 564. https://doi.org/10.3390/sym13040564

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