Inter- vs. Intramolecular Hydrogen Bond Patterns and Proton Dynamics in Nitrophthalic Acid Associates

Jóźwiak, Kinga; Jezierska, Aneta; Panek, Jarosław J.; Goremychkin, E. A.; Tolstoy, Peter M.; Shenderovich, Ilya G.; Filarowski, Aleksander

doi:10.3390/molecules25204720

Cited by 16 publications

(13 citation statements)

References 146 publications

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“…Note, that for IINS method the scattering cross-section for the deutron is much smaller than that of the proton and thus the contribution of the vibrations involving deutrons in IINS spectra is weak. The experimentally observed positions of γ(OH) bands and the H/D isotope effects on them are consistent with the literature data [ 49 , 50 , 51 ].…”

Section: Resultssupporting

confidence: 91%

Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline

et al. 2021

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The ortho-hydroxy aryl Schiff base 2-[(E)-(phenylimino)methyl]phenol and its deutero-derivative have been studied by the inelastic incoherent neutron scattering (IINS), infrared (IR) and Raman experimental methods, as well as by Density Functional Theory (DFT) and Density-Functional Perturbation Theory (DFPT) simulations. The assignments of vibrational modes within the 3500–50 cm−1 spectral region made it possible to state that the strong hydrogen bond in the studied compound can be classified as the so-called quasi-aromatic bond. The isotopic substitution supplemented by the results of DFT calculations allowed us to identify vibrational bands associated with all five major hydrogen bond vibrations. Quasi-isostructural polymorphism of 2-[(E)-(phenylimino)methyl]phenol (SA) and 2-[(E)-(phenyl-D5-imino)methyl]phenol (SA-C6D5) has been studied by powder X-ray diffraction in the 20–320 K temperature range.

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Section: Resultssupporting

confidence: 91%

Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline

et al. 2021

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“…Noncovalent interactions allow our world to exist. Their specific interaction energies [ 1 , 2 , 3 , 4 ], their effect on the spectral [ 5 , 6 , 7 ], chemical [ 8 , 9 ], and structural [ 10 , 11 , 12 ] properties of individual molecules, those in adducts and solutions [ 13 , 14 , 15 ], have been and remain vital to the progress of chemistry. The interpretation of spectral shifts caused by changes in the properties of a particular interaction can be carried out in sufficient detail [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Modeling of Solute-Solvent Interactions Using an External Electric Field—From Tautomeric Equilibrium in Nonpolar Solvents to the Dissociation of Alkali Metal Halides

Shenderovich

Денисов

2021

Molecules

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An implicit account of the solvent effect can be carried out using traditional static quantum chemistry calculations by applying an external electric field to the studied molecular system. This approach allows one to distinguish between the effects of the macroscopic reaction field of the solvent and specific solute–solvent interactions. In this study, we report on the dependence of the simulation results on the use of the polarizable continuum approximation and on the importance of the solvent effect in nonpolar solvents. The latter was demonstrated using experimental data on tautomeric equilibria between the pyridone and hydroxypyridine forms of 2,6-di-tert-butyl-4-hydroxy-pyridine in cyclohexane and chloroform.

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“…The presence of the hydrogen bonding is visible as well in the spectroscopy, e.g., in the Nuclear Magnetic Resonance (NMR), strong hydrogen bonds are revealed by downfield shifts in the

H NMR spectrum. In the infrared spectroscopy (IR), the hydrogen bonding shifts the X-H stretching frequency to lower energy (the decrease in the vibration frequency is observed) [ 27 , 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Competition of Intra- and Intermolecular Forces in Anthraquinone and Its Selected Derivatives

et al. 2021

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Intra- and intermolecular forces competition was investigated in the 9,10-anthraquinone (1) and its derivatives both in vacuo and in the crystalline phase. The 1,8-dihydroxy-9,10-anthraquinone (2) and 1,8-dinitro-4,5-dihydroxy-anthraquinone (3) contain Resonance-Assisted Hydrogen Bonds (RAHBs). The intramolecular hydrogen bonds properties were studied in the electronic ground and excited states employing Møller-Plesset second-order perturbation theory (MP2), Density Functional Theory (DFT) method in its classical formulation as well as its time-dependent extension (TD-DFT). The proton potential functions were obtained via scanning the OH distance and the dihedral angle related to the OH group rotation. The topological analysis was carried out on the basis of theories of Atoms in Molecules (AIM—molecular topology, properties of critical points, AIM charges) and Electron Localization Function (ELF—2D maps showing bonding patterns, calculation of electron populations in the hydrogen bonds). The Symmetry-Adapted Perturbation Theory (SAPT) was applied for the energy decomposition in the dimers. Finally, Car–Parrinello molecular dynamics (CPMD) simulations were performed to shed light onto bridge protons dynamics upon environmental influence. The vibrational features of the OH stretching were revealed using Fourier transformation of the autocorrelation function of atomic velocity. It was found that the presence of OH and NO2 substituents influenced the geometric and electronic structure of the anthraquinone moiety. The AIM and ELF analyses showed that the quantitative differences between hydrogen bonds properties could be neglected. The bridged protons are localized on the donor side in the electronic ground state, but the Excited-State Intramolecular Proton Transfer (ESIPT) was noticed as a result of the TD-DFT calculations. The hierarchy of interactions determined by SAPT method indicated that weak hydrogen bonds play modifying role in the organization of these crystal structures, but primary ordering factor is dispersion. The CPMD crystalline phase results indicated bridged proton-sharing in the compound 2.

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Inter- vs. Intramolecular Hydrogen Bond Patterns and Proton Dynamics in Nitrophthalic Acid Associates

Cited by 16 publications

References 146 publications

Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline

Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline

Modeling of Solute-Solvent Interactions Using an External Electric Field—From Tautomeric Equilibrium in Nonpolar Solvents to the Dissociation of Alkali Metal Halides

Competition of Intra- and Intermolecular Forces in Anthraquinone and Its Selected Derivatives

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