Revisiting the origin of the preferential π-π stacking conformation of the (+)-8-phenylmenthyl acrylate

Capim, Saulo Luís; Santana, Sidney R.; Oliveira, Boaz G.; Rocha, Gerd B.; Vasconcellos, Mário L. A. A.

doi:10.1590/s0103-50532010000900018

Cited by 24 publications

(12 citation statements)

References 17 publications

(24 reference statements)

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“…Also, note that ΔZPE values outweigh the BSSE results albeit in the halogen complexes they are almost compatible with one each other. Furthermore, the intermolecular strength of the halogen bond complexes is deeply weak just like is observed in dispersive intermolecular complexes [77] or even stacking structures [78], and in some cases here, particularly the IV complex, whose interaction seems to be repulsive. In this assertion, we would like to emphasize that energy decomposition analysis was not made, although we are willing to include this topic in our discussion not at this current time, but actually in future works [19][20][21].…”

Section: Mep Analysis Interaction Energies Charge Transfers and Chmentioning

confidence: 71%

The electronic mechanism ruling the dihydrogen bonds and halogen bonds in weakly bound systems of H3SiH···HOX and H3SiH···XOH (X = F, Cl, and Br)

et al. 2015

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The dihydrogen bond complexes (H 3 SiH•••HOX) and halogen bond complexes (H 3 SiH•••XOH) formed between SiH 4 and hypohalous acids HOX (X = F, Cl, and Br) have been studied at the MP2/6-311++G(2d,2p) computational level. The analyses of structure and infrared vibration frequencies have revealed tendencies in the red shifts and blue shifts of the stretch frequencies of the Si-H, H-O, and O-X bonds. Besides the computation of the interaction energies, punctual atomic charges and charge transference amounts were determined at light of the Natural Bond Orbital (NBO) approach, by which the quantifications of the s-and p-characters of hydrogen, oxygen, and silicon also were useful to unveil the frequency shifts aforementioned. With the purpose to elucidate the donor/acceptor interface along the charge transfer mechanism between the dihydrogen bonds and halogen bonds, the application of the hierarchical cluster analysis (HCA) and principal component analysis (PCA) chemometric techniques were useful in this regard. Moreover, the interaction strengths of the H 3 SiH•••HOX and H 3 SiH•••XOH complexes was computed through a model that embodies the frequency shifts and topological parameters derived from quantum theory of atoms in molecules (QTAIM).

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Section: Mep Analysis Interaction Energies Charge Transfers and Chmentioning

confidence: 71%

The electronic mechanism ruling the dihydrogen bonds and halogen bonds in weakly bound systems of H3SiH···HOX and H3SiH···XOH (X = F, Cl, and Br)

et al. 2015

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“…[84] In some cases, the pure functionals such as MPWB95 have been successfully used, [85] specially in studies of cubic molecules, but not cubane or prismane, actually the polyhedral fullerene. [86] As a matter of fact, despite the MPWB95 has been efficiently tested and approved in studies of noncovalent dimers, [87] molecules containing noble-gases, [88] or even intramolecular π-stacked structures, [89] the intermolecular condition to be described through the use of pure functionals is always a challenging task. In view of these notes, we have chosen the MPWB95 functional as our standard level of theory for carrying out the electronic structure calculations.…”

Section: Computational Approaches and Quantum Electronic Structure mentioning

confidence: 99%

The definitive challenge of forming uncommon pseudo‐π···H–F and C···H–F hydrogen bonds on cyclic and cubic nonpolar hydrocarbons

Santos

Carvalho

Oliveira

et al. 2020

J of Physical Organic Chem

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Due to the high symmetry and low polarity of the cyclopropane (C 3 H 6), cyclobutane (C 4 H 8), prismane (C 6 H 6), and cubane (C 8 H 8), it is widely known that these structures unlikely act as proton receptors to form intermolecular interactions with monoprotic acids, such as the hydrogen fluoride. Although the C 3 H 6 ÁÁÁHF, C 4 H 8 ÁÁÁHF, C 6 H 6 ÁÁÁHF, and C 8 H 8 ÁÁÁHF are weakly bound complexes, in this current work, all of them were definitively certified on the basis of a theoretical analysis. In according with the structural parameters and spectroscopy modes appraised through the density-functional theory calculations, the more accentuated perturbations are manifested in the hydrogen fluoride. The new hydrogen bond forms framed as pseudo-πÁÁÁH and CÁÁÁH were unveiled through the calculations of the quantum theory of atoms in molecules and natural bond orbital. In this context, the knowledge about the nature of these hydrogen bonds is necessary, wherein it used the symmetry-adapted perturbation theory for computing the contributions of the electrostatic, polarization, exchange, dispersion, and charge transfer terms. Lastly, the practical behavior of these hydrocarbons under the condition to form intermolecular interactions was examined by taking into account the solvent effect with calculations of the polarizable continuum model.

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“…If the potential electron energy density is outweighed by the kinetic, the positive profile of ∇ 2 ρ indicates a depletion of charge density along the inter-nuclear connecting Bond Path (BP) [33]. Furthermore, the atomic connection is recognized as close-shell interaction, which is often designated to H-bonds or other intermolecular weakly bound contacts, such as halogen bonds, dihydrogen bonds, and π-staking [34][35][36][37][38][39][40]. Regarding the values gathered in Table 4, it should be highlighted that the positive values of ∇ 2 ρ ensure that all H-bonds are closed-shell interactions due to the low charge density concentration.…”

Section: Aim Analysismentioning

confidence: 99%

Complex pairing of B2H4 with H2O, CH3OH, NH3, NH2CH3, NH(CH3)2 and N(CH3)3

Tayebee¹,

Zabardasti²

2017

Front Nanosci Nanotech

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Revisiting the origin of the preferential π-π stacking conformation of the (+)-8-phenylmenthyl acrylate

Cited by 24 publications

References 17 publications

The electronic mechanism ruling the dihydrogen bonds and halogen bonds in weakly bound systems of H3SiH···HOX and H3SiH···XOH (X = F, Cl, and Br)

The electronic mechanism ruling the dihydrogen bonds and halogen bonds in weakly bound systems of H3SiH···HOX and H3SiH···XOH (X = F, Cl, and Br)

The definitive challenge of forming uncommon pseudo‐π···H–F and C···H–F hydrogen bonds on cyclic and cubic nonpolar hydrocarbons

Complex pairing of B2H4 with H2O, CH3OH, NH3, NH2CH3, NH(CH3)2 and N(CH3)3

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