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Article

Sensitivity of Intra- and Intermolecular Interactions of Benzo[h]quinoline from Car–Parrinello Molecular Dynamics and Electronic Structure Inspection

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: Vincenzo Carravetta
Int. J. Mol. Sci. 2021, 22(10), 5220; https://doi.org/10.3390/ijms22105220
Received: 16 April 2021 / Revised: 3 May 2021 / Accepted: 5 May 2021 / Published: 14 May 2021
(This article belongs to the Section Physical Chemistry and Chemical Physics)
The O-H...N and O-H...O hydrogen bonds were investigated in 10-hydroxybenzo[h]quinoline (HBQ) and benzo[h]quinoline-2-methylresorcinol complex in vacuo, solvent and crystalline phases. The chosen systems contain analogous donor and acceptor moieties but differently coupled (intra- versus intermolecularly). Car–Parrinello molecular dynamics (CPMD) was employed to shed light onto principle components of interactions responsible for the self-assembly. It was applied to study the dynamics of the hydrogen bonds and vibrational features as well as to provide initial geometries for incorporation of quantum effects and electronic structure studies. The vibrational features were revealed using Fourier transformation of the autocorrelation function of atomic velocity and by inclusion of nuclear quantum effects on the O-H stretching solving vibrational Schrödinger equation a posteriori. The potential of mean force (Pmf) was computed for the whole trajectory to derive the probability density distribution and for the O-H stretching mode from the proton vibrational eigenfunctions and eigenvalues incorporating statistical sampling and nuclear quantum effects. The electronic structure changes of the benzo[h]quinoline-2-methylresorcinol dimer and trimers were studied based on Constrained Density Functional Theory (CDFT) whereas the Electron Localization Function (ELF) method was applied for all systems. It was found that the bridged proton is localized on the donor side in both investigated systems in vacuo. The crystalline phase simulations indicated bridged proton-sharing and transfer events in HBQ. These effects are even more pronounced when nuclear quantization is taken into account, and the quantized Pmf allows the proton to sample the acceptor area more efficiently. The CDFT indicated the charge depletion at the bridged proton for the analyzed dimer and trimers in solvent. The ELF analysis showed the presence of the isolated proton (a signature of the strongest hydrogen bonds) only in some parts of the HBQ crystal simulation. The collected data underline the importance of the intramolecular coupling between the donor and acceptor moieties. View Full-Text
Keywords: benzo[h]quinoline; gas phase; solvent; crystalline phase; CPMD; O-H stretching envelope; 1D and 2D Pmf; CDFT; ELF benzo[h]quinoline; gas phase; solvent; crystalline phase; CPMD; O-H stretching envelope; 1D and 2D Pmf; CDFT; ELF
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MDPI and ACS Style

Panek, J.J.; Zasada, J.; Szyja, B.M.; Kizior, B.; Jezierska, A. Sensitivity of Intra- and Intermolecular Interactions of Benzo[h]quinoline from Car–Parrinello Molecular Dynamics and Electronic Structure Inspection. Int. J. Mol. Sci. 2021, 22, 5220. https://doi.org/10.3390/ijms22105220

AMA Style

Panek JJ, Zasada J, Szyja BM, Kizior B, Jezierska A. Sensitivity of Intra- and Intermolecular Interactions of Benzo[h]quinoline from Car–Parrinello Molecular Dynamics and Electronic Structure Inspection. International Journal of Molecular Sciences. 2021; 22(10):5220. https://doi.org/10.3390/ijms22105220

Chicago/Turabian Style

Panek, Jarosław J., Joanna Zasada, Bartłomiej M. Szyja, Beata Kizior, and Aneta Jezierska. 2021. "Sensitivity of Intra- and Intermolecular Interactions of Benzo[h]quinoline from Car–Parrinello Molecular Dynamics and Electronic Structure Inspection" International Journal of Molecular Sciences 22, no. 10: 5220. https://doi.org/10.3390/ijms22105220

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