The Nature of Stacking Interactions between Organic Molecules Elucidated by Analysis of Crystal Structures.

Dahl, Tor; Kozma, Dávid; Ács, Mária; Weidlein, Johann; Schnöckel, Hansgeorg; Paulsen, Gudrun B.; Nielsen, Ruby I.; Olsen, Carl Erik; Pedersen, Christian; Stidsen, Carsten E.

doi:10.3891/acta.chem.scand.48-0095

Cited by 200 publications

(105 citation statements)

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“…The 3.3-3.6 Å interplanar distances in DHC is consistent with the range observed experimentally for stacked aromatic units 62 All three standard functional forms deviate significantly from the M06-2X description as the graphene-graphene separations are increased, as shown in Fig. 3 ͑the PD-Y PEC is similar to PD-X͒.…”

Section: A Structure and Energies Of Dhc Dimersupporting

confidence: 72%

Quantum mechanics based force field for carbon (QMFF-Cx) validated to reproduce the mechanical and thermodynamics properties of graphite

Pascal

Karasawa

Goddard

2010

The Journal of Chemical Physics

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As assemblies of graphene sheets, carbon nanotubes, and fullerenes become components of new nanotechnologies, it is important to be able to predict the structures and properties of these systems. A problem has been that the level of quantum mechanics practical for such systems ͑density functional theory at the PBE level͒ cannot describe the London dispersion forces responsible for interaction of the graphene planes ͑thus graphite falls apart into graphene sheets͒. To provide a basis for describing these London interactions, we derive the quantum mechanics based force field for carbon ͑QMFF-Cx͒ by fitting to results from density functional theory calculations at the M06-2X level, which demonstrates accuracies for a broad class of molecules at short and medium range intermolecular distances. We carried out calculations on the dehydrogenated coronene ͑C24͒ dimer, emphasizing two geometries: parallel-displaced X ͑close to the observed structure in graphite crystal͒ and PD-Y ͑the lowest energy transition state for sliding graphene sheets with respect to each other͒. A third, eclipsed geometry is calculated to be much higher in energy. The QMFF-Cx force field leads to accurate predictions of available experimental mechanical and thermodynamics data of graphite ͑lattice vibrations, elastic constants, Poisson ratios, lattice modes, phonon dispersion curves, specific heat, and thermal expansion͒. This validates the use of M06-2X as a practical method for development of new first principles based generations of QMFF force fields.

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Section: A Structure and Energies Of Dhc Dimersupporting

confidence: 72%

Quantum mechanics based force field for carbon (QMFF-Cx) validated to reproduce the mechanical and thermodynamics properties of graphite

Pascal

Karasawa

Goddard

2010

The Journal of Chemical Physics

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“…It seemsl ikely that electronic orbital and the lone pair electrons of N2 delocalized with p-electrons of thebenzenering. TheC11-N2distancewas foundtobe1.367(3)Å,which is consistentwithdouble bond character.The interplanardistance(3.4 Å) agrees well with the observation that crystals of many aromatic molecules form stacks with approximately parallel molecular planes separated by 3.3~3.6 Å [ 5]. Other prevalent interactions found in the crystal are intermolecular C-H···p interactions.…”

Section: Discussionsupporting

confidence: 75%

Crystal structure of 2-(4-diethylamino-2-hydroxyphenyl)-benzoxazole, C17H18N2O2

Zhang

et al. 2013

Zeitschrift Für Kristallographie - New Crystal Structures

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“…8,9 Certain drugs rely on π-π interactions for intercalation into DNA. 10,11 While these interactions have been studied extensively, [12][13][14][15][16][17][18][19][20][21][22][23][24] their relative weakness and shallow potential energy surface makes them challenging to describe by either experiment or theory. [25][26][27][28][29] The binding energy of the gas-phase benzene dimer, for example, is 2-3 kcal/mol, and the dimer is stable only at low temperatures.…”

Section: Introductionmentioning

confidence: 99%

Modeling π–π Interactions with the Effective Fragment Potential Method: The Benzene Dimer and Substituents

2008

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This study compares the results of the general effective fragment potential (EFP2) method to the results of a previous combined coupled cluster with single, double, and perturbative triple excitations [CCSD(T)] and symmetry-adapted perturbation theory (SAPT) study [Sinnokrot and Sherrill, J. Am. Chem. Soc., 2004, 126, 7690] on substituent effects in π-π interactions. EFP2 is found to accurately model the binding energies of the benzene-benzene, benzene-phenol, benzene-toluene, benzene-fluorobenzene, and benzene-benzonitrile dimers, as compared with high-level methods [Sinnokrot and Sherrill, J. Am. Chem. Soc., 2004, 126, 7690], but at a fraction of the computational cost of CCSD(T). In addition, an EFP-based Monte Carlo/simulated annealing study was undertaken to examine the potential energy surface of the substituted dimers.

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The Nature of Stacking Interactions between Organic Molecules Elucidated by Analysis of Crystal Structures.

Cited by 200 publications

References 0 publications

Quantum mechanics based force field for carbon (QMFF-Cx) validated to reproduce the mechanical and thermodynamics properties of graphite

Quantum mechanics based force field for carbon (QMFF-Cx) validated to reproduce the mechanical and thermodynamics properties of graphite

Crystal structure of 2-(4-diethylamino-2-hydroxyphenyl)-benzoxazole, C17H18N2O2

Modeling π–π Interactions with the Effective Fragment Potential Method: The Benzene Dimer and Substituents

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