Intramolecular Hydrogen Bonds in Selected Aromatic Compounds: Recent Developments

Jezierska, Aneta; Tolstoy, Peter M.; Panek, Jarosław J.; Filarowski, Aleksander

doi:10.3390/catal9110909

Cited by 15 publications

(13 citation statements)

References 85 publications

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“…Nevertheless, there are still some open questions related to the proton transfer phenomenon, the strength of the interaction or to the environmental effects influence on the hydrogen bonding features. The steric and inductive effects play an important role in the modulation of the hydrogen bridge [ 29 , 30 ] determining the bridged proton position. The presence of the intramolecular hydrogen bond is associated with the quasi-ring formation and further with the internal reorganization of the geometric parameters and electronic structure.…”

Section: Introductionmentioning

confidence: 99%

Non-Covalent Forces in Naphthazarin—Cooperativity or Competition in the Light of Theoretical Approaches

Jezierska

Błaziak

Klahm

et al. 2021

IJMS

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Non-covalent interactions responsible for molecular features and self-assembly in Naphthazarin C polymorph were investigated on the basis of diverse theoretical approaches: Density Functional Theory (DFT), Diffusion Quantum Monte Carlo (DQMC), Symmetry-Adapted Perturbation Theory (SAPT) and Car-Parrinello Molecular Dynamics (CPMD). The proton reaction paths in the intramolecular hydrogen bridges were studied. Two potential energy minima were found indicating that the proton transfer phenomena occur in the electronic ground state. Diffusion Quantum Monte Carlo (DQMC) and other levels of theory including Coupled Cluster (CC) employment enabled an accurate inspection of Potential Energy Surface (PES) and revealed the energy barrier for the proton transfer. The structure and reactivity evolution associated with the proton transfer were investigated using Harmonic Oscillator Model of Aromaticity - HOMA index, Fukui functions and Atoms In Molecules (AIM) theory. The energy partitioning in the studied dimers was carried out based on Symmetry-Adapted Perturbation Theory (SAPT) indicating that dispersive forces are dominant in the structure stabilization. The CPMD simulations were performed at 60 K and 300 K in vacuo and in the crystalline phase. The temperature influence on the bridged protons dynamics was studied and showed that the proton transfer phenomena were not observed at 60 K, but the frequent events were noticed at 300 K in both studied phases. The spectroscopic signatures derived from the CPMD were computed using Fourier transformation of autocorrelation function of atomic velocity for the whole molecule and bridged protons. The computed gas-phase IR spectra showed two regions with OH absorption that covers frequencies from 2500 cm−1 to 2800 cm−1 at 60 K and from 2350 cm−1 to 3250 cm−1 at 300 K for both bridged protons. In comparison, the solid state computed IR spectra revealed the environmental influence on the vibrational features. For each of them absorption regions were found between 2700–3100 cm−1 and 2400–2850 cm−1 at 60 K and 2300–3300 cm−1 and 2300–3200 cm−1 at 300 K respectively. Therefore, the CPMD study results indicated that there is a cooperation of intramolecular hydrogen bonds in Naphthazarin molecule.

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Section: Introductionmentioning

confidence: 99%

Non-Covalent Forces in Naphthazarin—Cooperativity or Competition in the Light of Theoretical Approaches

Jezierska

Błaziak

Klahm

et al. 2021

IJMS

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“…As the title indicates, this review is dealing with intramolecular hydrogen bonding. Recent reviews cover this subject [ 1 , 2 ]. Review [ 1 ] concentrates on Schiff bases made from salicylaldehyde and TRIS.…”

Section: Introductionmentioning

confidence: 99%

“…Rules are set up to predict the predominant tautomer based on linear free energy relationships. Review [ 2 ] is focused on aromatic systems such as o -hydroxy Schiff bases and Mannich bases and mainly deals with tautomerism. However, in order to make it feasible within the limits of a review of this type, tautomeric systems as such are not dealt with.…”

Section: Introductionmentioning

confidence: 99%

A Spectroscopic Overview of Intramolecular Hydrogen Bonds of NH…O,S,N Type

Hansen

2021

Molecules

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Intramolecular NH…O,S,N interactions in non-tautomeric systems are reviewed in a broad range of compounds covering a variety of NH donors and hydrogen bond acceptors. 1H chemical shifts of NH donors are good tools to study intramolecular hydrogen bonding. However in some cases they have to be corrected for ring current effects. Deuterium isotope effects on 13C and 15N chemical shifts and primary isotope effects are usually used to judge the strength of hydrogen bonds. Primary isotope effects are investigated in a new range of magnitudes. Isotope ratios of NH stretching frequencies, νNH/ND, are revisited. Hydrogen bond energies are reviewed and two-bond deuterium isotope effects on 13C chemical shifts are investigated as a possible means of estimating hydrogen bond energies.

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“…Although, large basis sets are needed to calculate the 31 P NMR CSA tensors correctly and to reach the limiting value of the isotropic absolute chemical shielding, much smaller basis sets are required to obtain a narrow confidence range of σ ref . Therefore, different effects (such as isotope effect, [33] proton exchange, [34] intra‐ [35] and intermolecular [34] noncovalent interactions, and conformation [36] ) on 31 P isotropic chemical shift can be studied using small basis sets for large molecular systems.…”

Section: Discussionmentioning

confidence: 99%

“…Therefore, different effects (such as isotope effect, [33] proton exchange, [34] intra- [35] and intermolecular [34] noncovalent inter- actions, and conformation [36] ) on P isotropic chemical shift can be studied using small basis sets for large molecular systems.…”

Section: Discussionmentioning

confidence: 99%

Experimentally Established Benchmark Calculations of ³¹P NMR Quantities

Shenderovich

2020

Chemistry Methods

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The accuracy of different density function theory functionals and the MP2 approximation in 31P NMR calculations has been evaluated for ten phosphorous containing molecules in which the phosphorous atoms are not involved in intermolecular interactions. The obtained absolute chemical shielding tensors are compared to experimental ones. The dependence of the numerical values on the size of basis sets has been inspected from the 6‐311G(2d,p) to the pcSseg‐3 basis sets. General recommendations on the most reliable functionals and the smallest possible size of a basis set have been reported. For example, the use of the M06 L functional should be avoided. For five polycrystalline samples, the conformation of molecules has been identified with a high precision. These structures have been used to determine the reference values of the absolute chemical shielding for the TPSSh, B3LYP, and ωB97XD functionals and different basis sets. As reported in the supporting information, these structures can be used to determine the reference value of the absolute chemical shielding for any approximation of interest.

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Intramolecular Hydrogen Bonds in Selected Aromatic Compounds: Recent Developments

Cited by 15 publications

References 85 publications

Non-Covalent Forces in Naphthazarin—Cooperativity or Competition in the Light of Theoretical Approaches

Non-Covalent Forces in Naphthazarin—Cooperativity or Competition in the Light of Theoretical Approaches

A Spectroscopic Overview of Intramolecular Hydrogen Bonds of NH…O,S,N Type

Experimentally Established Benchmark Calculations of ³¹P NMR Quantities

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Intramolecular Hydrogen Bonds in Selected Aromatic Compounds: Recent Developments

Cited by 15 publications

References 85 publications

Non-Covalent Forces in Naphthazarin—Cooperativity or Competition in the Light of Theoretical Approaches

Non-Covalent Forces in Naphthazarin—Cooperativity or Competition in the Light of Theoretical Approaches

A Spectroscopic Overview of Intramolecular Hydrogen Bonds of NH…O,S,N Type

Experimentally Established Benchmark Calculations of 31P NMR Quantities

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Product

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Experimentally Established Benchmark Calculations of ³¹P NMR Quantities