Revealing Noncovalent Interactions

Johnson, Erin R.; Keinan, Shahar; Mori‐Sánchez, Paula; Contreras‐García, Julia; Cohen, Aron J.; Yang, Weitao

doi:10.1021/ja100936w

Cited by 7,181 publications

(5,761 citation statements)

References 53 publications

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“…40 They can be either, as shown by the results for the CH 4-x F x dimers ( Figure S7). According to our NCI results, which was here performed for noncovalent interactions, but could also be applied to the covalent framework, 16 the CF···FC interaction is attractive in compounds 1-3. We now turn to a critical analysis of this finding.…”

Section: Resultsmentioning

confidence: 99%

“…28 NCI calculations were also performed on the obtained MP2/aug-cc-pVDZ electron densities by using the NCIPLOT 3.0 program. 16 In addition, geometry optimisations, QTAIM and NCI calculations were performed at selected levels of density functional theory (DFT) with a variety of basis sets. These results are deposited in the electronic supplementary information (ESI).…”

Section: Computational Detailsmentioning

confidence: 99%

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Analysis of CF···FC Interactions on Cyclohexane and Naphthalene Frameworks

et al. 2014

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Intramolecular CF···FC interactions in selected organofluorine compounds (all-syn-1,2,3,4-and all-syn-1,2,4,5-tetrafluorocyclohexane, 1,8-difluoronaphthalene, 4,5-difluorophenanthrene, 2,2',5,5'-tetrafluorobiphenyl) were studied at the MP2/aug-ccpVDZ level using the recently developed noncovalent interaction (NCI) method. For the optimised minima, all CF···FC interactions that are identified by this method are classified as attractive, also in those cases where suitable isodesmic reaction energies fail to provide evidence for an energetic stabilisation. Possible relations between these interactions and the observable J FF spin-spin coupling constant values are discussed.

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Section: Resultsmentioning

confidence: 99%

Section: Computational Detailsmentioning

confidence: 99%

Analysis of CF···FC Interactions on Cyclohexane and Naphthalene Frameworks

et al. 2014

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“…Several schemes have been proposed in the last decades to extract from ρ(r) as much chemical information as possible, which involve its visualization (profiles, 2D maps, 3D graphical representations), partition according to different schemes, topological analysis, etc. [4][5][6][7][8][9][10][11][12][13][14][15] In this respect, one of the most powerful and popular techniques is represented by Bader's quantum theory of atoms in molecules (QTAIM), which relies on the topological analysis of ρ(r). 16 If a routine analysis of the wave-function |Ψ of a small system is a non particularly demanding task from a computational point of view (when compared to the convergence of the self-consistent field, SCF, procedure or to the analytical evaluation of energy gradients), this is clearly no more the case either when rather sophisticated techniques are adopted (such as QTAIM) or when large systems are studied.…”

Section: Introductionmentioning

confidence: 99%

Electron density analysis of large (molecular and periodic) systems: A parallel implementation

et al. 2015

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A parallel implementation is presented of a series of algorithms for the evaluation of several oneelectron properties of large molecular and periodic (of any dimensionality) systems. The electron charge and momentum densities of the system, the electrostatic potential, X-ray structure factors, directional Compton profiles can be effectively evaluated at low computational cost along with a full topological analysis of the electron charge density of the system according to Bader's quantum theory of atoms in molecules. The speedup of the parallelization of the different algorithms is presented. The search of all symmetry-irreducible critical points of the electron charge density of the crystallized crambin protein and the evaluation of all the corresponding bond paths, for instance, would require about 32 days if run in serial mode and reduces to less than 2 days when run in parallel mode over 32 processors.

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“…The NCI method calculates an index based on the electron density and the electron density gradient. 41 This index presents singularities at low density when a weak interaction appears between two fragments. The strength of these interactions can also be calculated and isosurfaces can be plotted to visualize the domains of noncovalent interactions.…”

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confidence: 99%

2-Hydroxypyridine-N-oxide-Embedded Aurones as Potent Human Tyrosinase Inhibitors

Haudecoeur

Carotti

Gouron

et al. 2016

ACS Med. Chem. Lett.

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With the aim to develop effective and selective human tyrosinase inhibitors, we investigated aurone derivatives whose B-ring was replaced by a non-oxidizable 2-hydroxypyridine-N-oxide (HOPNO) moiety. These aurones were synthesized and evaluated as inhibitors of purified human tyrosinase. Excellent inhibition activity was revealed and rationalized by theoretical calculations. The aurone backbone was especially found to play a crucial role, as the HOPNO moiety alone provided very modest activity on human tyrosinase. Furthermore, the in vitro activity was confirmed by measuring the melanogenesis suppression ability of the compounds in melanoma cell lysates and whole cells. Our study reveals that HOPNO-embedded 6-hydroxyaurone is to date the most effective inhibitor of isolated human tyrosinase. Owing to its low toxicity and its high inhibition activity, it could represent a milestone on the path toward new valuable agents in dermocosmetics, as well as in medical fields where it was recently suggested that tyrosinase could play key roles.

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Revealing Noncovalent Interactions

Cited by 7,181 publications

References 53 publications

Analysis of CF···FC Interactions on Cyclohexane and Naphthalene Frameworks

Analysis of CF···FC Interactions on Cyclohexane and Naphthalene Frameworks

Electron density analysis of large (molecular and periodic) systems: A parallel implementation

2-Hydroxypyridine-N-oxide-Embedded Aurones as Potent Human Tyrosinase Inhibitors

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