Predicting face-to-face arene–arene binding energies

Beg, Shana; Waggoner, Kristine; Yaraghi, Ahmad; Watt, Michelle; Lewis, Michael

doi:10.1016/j.cplett.2008.02.043

Cited by 29 publications

(21 citation statements)

References 27 publications

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“…Notably, Lewis et al [29] showed that there was no correlation between the quadrupole moment of the halogenated ring and the predicted interaction energy.…”

Section: Sandwich Dimermentioning

confidence: 98%

“…The following year, Lewis and coworkers [29] examined the effect of halogen substituents on the benzene sandwich dimer, showing a correlation between the sum of s p constants and MP2 stacking interaction energies. Notably, Lewis et al [29] showed that there was no correlation between the quadrupole moment of the halogenated ring and the predicted interaction energy.…”

Section: Sandwich Dimermentioning

confidence: 98%

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Substituent Effects on Non‐Covalent Interactions with Aromatic Rings: Insights from Computational Chemistry

et al. 2011

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Non-covalent interactions with aromatic rings pervade modern chemical research. The strength and orientation of these interactions can be tuned and controlled through substituent effects. Computational studies of model complexes have provided a detailed understanding of the origin and nature of these substituent effects, and pinpointed flaws in entrenched models of these interactions in the literature. Here, we provide a brief review of efforts over the last decade to unravel the origin of substituent effects in π-stacking, XH/π, and ion/π interactions through detailed computational studies. We highlight recent progress that has been made, while also uncovering areas where future studies are warranted.

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“…Notably, Lewis et al [29] showed that there was no correlation between the quadrupole moment of the halogenated ring and the predicted interaction energy.…”

Section: Sandwich Dimermentioning

confidence: 98%

Section: Sandwich Dimermentioning

confidence: 98%

Substituent Effects on Non‐Covalent Interactions with Aromatic Rings: Insights from Computational Chemistry

et al. 2011

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“…Starting in the early 2000s, Sherrill and co-workers, [17,18,22,23,45,46,[64][65][66][67][68][69][82][83][84][85] as well as others, [5,[75][76][77]86] began publishing systematic, high-accuracy gas-phase interaction energies for prototypical stacked dimers of benzene and substituted benzenes. The data quickly revealed unexpected substituent effects for these gas-phase dimers, [18,[64][65][66][67] kicking off a frenzy of computational and experimental studies of substituent effects in π-stacking interactions.…”

Section: Unexpected Substituent Effects In the Benzene Dimermentioning

confidence: 98%

Unraveling the Origin of Substituents Effects in π-Stacking Interactions

Wheeler

2015

Challenges and Advances in Computational Chemistry and Physics

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Non-covalent interactions involving aromatic rings, which include π-stacking, anion-π, and cation-π interactions, among others, are central to modern chemical research. These interactions play vital roles in everything from protein-DNA interactions and the properties of organic electronic materials to stereoselective organocatalyzed reactions. We discuss recent efforts to understand the impact of substituents on the strength of π-stacking interactions through the application of modern tools of computational quantum chemistry. We first provide an account of previous efforts to develop qualitative physical models of these interactions, followed by apparent flaws in these previous models. We then present our local, direct interaction model of substituent effects in π-stacking interactions, and discuss recent extensions of this model based on the examination of electric fields of arenes. We also discuss related misconceptions regarding molecular electrostatic potentials (ESPs), and offer a simpler view of the origin of ESP differences arising from the incorporation of heteroatoms or substituents into aromatic rings. Finally, we conclude with an outlook for future advances in our understanding of π-stacking interactions.

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“…Computational results [10,13,16,17] have shown that all substituents enhance the pp stacking interactions. Another computational study on the p-p interactions of benzene and poly-halo-substituted aromatics [18] showed that the sum of the Hammett constants ( P r p ) correlate very well with the binding energies. In pyridine-substituted benzene complexes, the H-bond ability of the nitrogen atom of the pyridine is related to the p-p stacking interactions [19,20].…”

Section: Introductionmentioning

confidence: 96%

Investigation of the effect of π–π stacking interaction on the properties of –CONH2 functional group of benzamide

Momeni

Ebrahimi

2015

Struct Chem

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The effect of p-p stacking between substituted benzene and benzamide on the properties of -CONH 2 functional group, as an important unit in the drugs activities, was studied at the M06-2X/6-311??G(d,p) level of theory. All substituents enhanced the p-p interaction energies, where a reasonably good correlation was found between the interaction energies and Hammett constants of substituents. A linear correlation is observed between the sum of electron charge density at the cage critical point P q ccp obtained from the atoms in molecules (AIM) analysis and the interaction energies, where both values grow up with electron-withdrawing substituents (EWSs). The electrostatic potential around the O and N atoms, the natural charges, and the dipole moment of C=O bond have been calculated to predict the ability of functional group on the electrophilic and nucleophilic attacks. The charge transfer increases the electrostatic potential around the benzamide functional group in the presence of electrondonating substituents (EDSs). EWSs increase the acidity of the N atom of the -NH 2 group; a linear relationship is observed between the acidity calculated with the molecular electrostatic potential around the N atom and the natural valence orbital energies.

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Predicting face-to-face arene–arene binding energies

Cited by 29 publications

References 27 publications

Substituent Effects on Non‐Covalent Interactions with Aromatic Rings: Insights from Computational Chemistry

Substituent Effects on Non‐Covalent Interactions with Aromatic Rings: Insights from Computational Chemistry

Unraveling the Origin of Substituents Effects in π-Stacking Interactions

Investigation of the effect of π–π stacking interaction on the properties of –CONH2 functional group of benzamide

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