Is Electrostatics Sufficient to Describe Hydrogen‐Bonding Interactions?

Hoja, Johannes; Sax, Alexander F.; Szalewicz, Krzysztof

doi:10.1002/chem.201303528

Cited by 62 publications

(100 citation statements)

References 33 publications

(45 reference statements)

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“…54 Recently, this formula has been successfully tested to reproduce the binding energy values of alcohols. 55 In addition, it improves the success rate of predicting relative stabilities in the full S66 test set of typical biomolecular complexes ( Figure 3). …”

Section: ■ Results and Discussionmentioning

confidence: 97%

Physical Nature of Fatty Acid Amide Hydrolase Interactions with Its Inhibitors: Testing a Simple Nonempirical Scoring Model

Giedroyć-Piasecka¹,

Dyguda-Kazimierowicz²,

Beker³

et al. 2014

J. Phys. Chem. B

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Fatty acid amide hydrolase (FAAH) is an enzyme responsible for the deactivating hydrolysis of fatty acid ethanolamide neuromodulators. FAAH inhibitors have gained considerable interest due to their possible application in the treatment of anxiety, inflammation, and pain. In the context of inhibitor design, the availability of reliable computational tools for predicting binding affinity is still a challenging task, and it is now well understood that empirical scoring functions have several limitations that in principle could be overcome by quantum mechanics. Herein, systematic ab initio analyses of FAAH interactions with a series of inhibitors belonging to the class of the N-alkylcarbamic acid aryl esters have been performed. In contrast to our earlier studies of other classes of enzyme-inhibitor complexes, reasonable correlation with experimental results required us to consider correlation effects along with electrostatic term. Therefore, the simplest comprehensive nonempirical model allowing for qualitative predictions of binding affinities for FAAH ligands consists of electrostatic multipole and second-order dispersion terms. Such a model has been validated against the relative stabilities of the benchmark S66 set of biomolecular complexes. As it does not involve parameters fitted to experimentally derived data, this model offers a unique opportunity for generally applicable inhibitor design and virtual screening.

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Section: ■ Results and Discussionmentioning

confidence: 97%

Physical Nature of Fatty Acid Amide Hydrolase Interactions with Its Inhibitors: Testing a Simple Nonempirical Scoring Model

Giedroyć-Piasecka¹,

Dyguda-Kazimierowicz²,

Beker³

et al. 2014

J. Phys. Chem. B

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“…Even in the water dimer, about 50% of the interaction energy is due to dispersion interaction, as we showed in a recent study on alcohol dimers. 23 In this study, we showed also that the importance of the dispersion component increases with the size and bulk of the molecules, because the number of atoms in close contact also increases with size. In the tert-butanol dimer, the dispersion interaction is responsible for about 90% of the dimer stabilization energy at the equilibrium geometry, with the sum of electrostatic, induction, and exchange interactions amounting to only 10%.…”

Section: ■ Introductionmentioning

confidence: 83%

Adsorption of Glucose, Cellobiose, and Cellotetraose onto Cellulose Model Surfaces

2014

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Reliable simulation of molecular adsorption onto cellulose surfaces is essential for the design of new cellulose nanocomposite materials. However, the applicability of classical force field methods to such systems remains relatively unexplored. In this study, we present the adsorption of glucose, cellobiose, and cellotetraose on model surfaces of crystalline cellulose Iα and Iβ. The adsorption of the two large carbohydrates was simulated with the GLYCAM06 force field. To validate this approach, quantum theoretical calculations for the adsorption of glucose were performed: Equilibrium geometries were studied with density functional theory (DFT) and dispersion-corrected DFT, whereas the adsorption energies were calculated with two standard density functional approximations and five dispersion-containing DFT approaches. We find that GLYCAM06 gives a good account of geometries and, in most cases, accurate adsorption energies when compared to dispersion-corrected DFT energies. Adsorption onto the (100) surface of cellulose Iα is, in general, stronger than onto the (100) surface of cellulose Iβ. Contrary to intuition, the adsorption energy is not directly correlated with the number of hydrogen bonds; rather, it is dominated by dispersion interactions. Especially for bigger adsorbates, a neglect of these interactions leads to a dramatic underestimation of adsorption energies.

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“…111, the relative weight of each component, defined as w = |E i |/ i |E i |, with E i denoting the different interaction energy contributions. We see that for most systems the energy decomposition describes a bonding behavior quite similar to conventional hydrogen bonds [112], despite for the present dihydrogen Table IV]. Interaction energy (kcal/mol) for the dihydrogen bond complexes.…”

Section: Energy Decomposition Analysismentioning

confidence: 71%

Wave Function and Density Functional Theory Studies of Dihydrogen Complexes

Fabiano

Constantin

Sala

2014

J. Chem. Theory Comput.

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We performed a benchmark study on a series of dihydrogen bond complexes and constructed a set of reference bond distances and interaction energies. The test set was employed to assess the performance of several wave-function correlated and density functional theory methods. We found that second-order correlation methods describe relatively well the dihydrogen complexes. However, for high accuracy inclusion of triple contributions is important. On the other hand, none of the considered density functional methods can simultaneously yield accurate bond lengths and interaction energies. However, we found that improved results can be obtained by the inclusion of non-local exchange contributions.

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Is Electrostatics Sufficient to Describe Hydrogen‐Bonding Interactions?

Cited by 62 publications

References 33 publications

Physical Nature of Fatty Acid Amide Hydrolase Interactions with Its Inhibitors: Testing a Simple Nonempirical Scoring Model

Physical Nature of Fatty Acid Amide Hydrolase Interactions with Its Inhibitors: Testing a Simple Nonempirical Scoring Model

Adsorption of Glucose, Cellobiose, and Cellotetraose onto Cellulose Model Surfaces

Wave Function and Density Functional Theory Studies of Dihydrogen Complexes

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