How Different are Electron-Rich and Electron-Deficient π Interactions?

Geronimo, Inacrist; Lee, Eun Cheol; Singh, N. Jiten; Kim, Kwang S.

doi:10.1021/ct100182u

Cited by 60 publications

(50 citation statements)

References 34 publications

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“…This phenomenon is opposite to the substituent effect in the substituted benzene systems C 6 H 5 …X, 18,26 where the binding was enhanced due to the substituent groups, such as X=F, CH 3 , NH 2 , OH, etc. The current result supports the previous report that the two N atoms in the histidine ring behave very differently in π interaction from benzene 28 …”

Section: Resultssupporting

confidence: 93%

Substituent effects in π-stacking of histidine on functionalized-SWNT and graphene

Wang

2015

Computational and Theoretical Chemistry

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Adsorptions of histidine on the functionalized (10,0) single-walled carbon nanotube (SWNT) and graphene were investigated using density function theory methods, M05-2x and DFT-D. The results show that the binding of the histidine ring to the functionalized SWNT is weaker than that to the pristine SWNT for both singlet and triplet complexes, regardless of the electron-donating (-OH, -NH2) or electron-withdrawing (-COOH) character and their attached sites. The present decreased binding is opposite to the well-known enhanced binding in the substituted benzene dimers. Since the atoms of the histidine are distant from the substituent atoms by over 6Å, there would be no direct interaction between histidine and the substituent as in the case of the substituted benzene systems. The decreased binding can be mainly driven by the aromaticity of the functionalized SWNT. The nucleus-independent chemical shift (NICS) index analysis for the functionalized SWNTs in deed shows that local aromaticity of SWNT is decreased because of the electron redistribution induced by functional groups, and the π-π stacking between the histidine ring and functionalized-SWNT is therefore decreased as compared to the pristine SWNT. However, the above trend does not remain for the binding between the histidine and graphene. The binding of the histidine to the functionalized graphene with -OH and -NH2 is just slightly weaker than that to the pristine graphene, while its binding to COOH-SWNT becomes a little bit stronger.

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Section: Resultssupporting

confidence: 93%

Substituent effects in π-stacking of histidine on functionalized-SWNT and graphene

Wang

2015

Computational and Theoretical Chemistry

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“…The SAPT2 energy component analysis of pyridine dimers [56] ( Ab initio investigation on p dimers of N-heterocycles (pyridine (Py), pyrazine (Pz), triazine (Tz), and tetrazine (Tt) in stacked (S), displaced-stacked (D), and T-shaped series (T)) using the Cambridge Structural Database showed stacked/displaced-stacked preference in their conformations. [57] Although the dispersion effect is dominating in stacked/displacedstacked dimers, their relative stabilities are controlled by electrostatic effects (Fig. 5).…”

Section: Review Wwwq-chemorgmentioning

confidence: 99%

Functional molecules and materials by π‐Interaction based quantum theoretical design

Tehrani

Kim

2016

Int J of Quantum Chemistry

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The intermolecular and intramolecular noncovalent interactions involving p-aromatic compounds have attracted increasing attention over the last decades in chemistry, biology and material sciences. In this review, we discuss contemporary computational studies on the nature and strength of H-p, p-p, and anion-p interactions. We emphasize how modern quantum theoretical approaches ahead of experiment can provide insight into the design of new materials and devices by tuning the p-interactions in cooperative and competitive manners. Usefulness of such approaches towards designing new materials is demonstrated with some examples of molecular recognition/sensing, self-assembly/engineering, receptors, catalysts, supramolecules, graphene, and other two-dimensional (2D) materials/devices.

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“…Interactions between two pyridine molecules were calculated at high levels of quantum chemistry, giving two energy minima, similar to ones found for benzene-benzene dimer [43]. Stacking interactions of two pyridines are, however, somewhat stronger than CH/π interactions (interaction energies are −3.80 and −3.56 kcal/mol, respectively) [58]. Recently, study on pyridine-pyridine interactions at large horizontal displacement was performed [23], and it will be discussed in this section.…”

Section: Heteroaromatic/heteroaromatic Interactions At Large Horizontmentioning

confidence: 56%

“…14.28) showed clear preference for head-to-tail orientation, which is the most stable orientation found by performing quantum chemical calculations [58]. The parameter T (torsion angle N-Ω-Ω′-N′, Fig.…”

Section: Cambridge Structural Database Search For Pyridine-pyridine Imentioning

confidence: 78%

Parallel Interactions of Aromatic Molecules at Large Horizontal Displacements

Malenov

Zarić

2016

Non‐covalent Interactions in the Synthesis and Design of New Compounds

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How Different are Electron-Rich and Electron-Deficient π Interactions?

Cited by 60 publications

References 34 publications

Substituent effects in π-stacking of histidine on functionalized-SWNT and graphene

Substituent effects in π-stacking of histidine on functionalized-SWNT and graphene

Functional molecules and materials by π‐Interaction based quantum theoretical design

Parallel Interactions of Aromatic Molecules at Large Horizontal Displacements

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