Nonempirical calculations on hydrogen-bonded and stacked structures of p-benzoquinone—hydroquinone pyridine—pyrrole and pyridine-phenol complexes

Foucrault, M.; Hobza, Pavel; Sándorfy, C.

doi:10.1016/0166-1280(87)87002-1

Cited by 8 publications

(2 citation statements)

References 17 publications

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Section: Introductionmentioning

confidence: 86%

“…In an early paper dealing with p -benzoquinone−hydroquinone, pyridine−pyrrole, and pyridine−phenol stacking, the stacking interaction was studied at the Hartree−Fock level in combination with a London type expression for the dispersion energy . As expected, the Hartree−Fock contribution was found to be repulsive, while the stabilization of the stacking came exclusively from the dispersion energy . In their study of the face-to-face interaction between polycyclic aromatic hydrocarbons and nitrated benzenes, Heard and Boyd 24 claimed that interaction energies was dependent on the quadrupole moment, and apparently for these complexes dispersion effects do not contribute significantly to the binding energy.…”

Section: Introductionmentioning

confidence: 91%

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Intermolecular Interactions in p-Chlorobenzoic Acid Dimers

1998

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The molecular structure of the parallel orientation of the p-chlorobenzoic acid dimer has been studied at the second-order Møller-Plesset level using split-valence-quality basis sets augmented by polarization functions. In the obtained dimer structure, the Cl atoms are located behind the carboxyl groups of the neighboring monomer, while in crystalline copper and nickel p-chlorobenzoate complexes, the Cl atoms and the benzene nuclei form a parallel displaced umbrella structure with the Cl atoms mutually above the center of the respective benzene ring. The interaction energy for the parallel p-chlorobenzoic acid dimer complex is calculated at the second-order Møller-Plesset level to be 5.1 kcal mol -1 . The intermolecular attraction is mainly due to dispersion effects between the aromatic rings. The obtained distance between the benzene nuclei of 343 pm is in agreement with the experimental values of 341.6 and 366.6 pm measured for nickel and copper p-chlorobenzoate complexes, respectively. At the second-order Møller-Plesset level, the umbrella structure is found to be bound by 2.6 kcal mol -1 , as compared to infinite separations, with a chlorine-ring distance of 364 pm. However, at the second-order Møller-Plesset level, the umbrella structure is not a local minimum.

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Section: Introductionmentioning

confidence: 86%

Section: Introductionmentioning

confidence: 91%

Intermolecular Interactions in p-Chlorobenzoic Acid Dimers

1998

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Internal and External Implications of the Structure of Hydrogen Bonded Complexes . Ii. Mndo‐pm3 Studies on the Structure of the 4‐methylpyridine Complex With Pentachlorophenol

Koll

Majerz

1994

Bulletin des Soc Chimique

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The structure of the complex of 4-methylpyridine with pentachlorophenol in the gas phase was determined by the MNDO-PM3 procedure and compared with the experimental crystallographic structure. The calculated potential for internal rotation around the hydrogen bond axis predicts a free rotation in the gas phase and a large ability of the complex to adapt its shape to the requirements of the crystal packing. The influence of different internal and external factors on the structure of the studied complex is discussed.

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Decomposition analyses of the intermolecular interaction energies in two ππ stacking complexes: Quinhydrone and N,N,N′, N′‐tetramethyl‐P‐diaminobenzene‐chloranil complex

Kurita¹,

Takayama²,

Tanaka³

1994

J Comput Chem

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Although there is a similarity in the orbital interaction scheme between quinhydrone and N,N,N′,N′‐tetramethyl‐p‐diaminobenzene‐chloranil complex, the stacking conformations are different from each other. The former prefers the half‐stacked conformation, whereas the latter prefers the completely stacked conformation. We have done ab initio molecular orbital calculations and decomposition analyses of the intermolecular interaction energies to clarify the origin of the different stacking conformations. It was concluded that the main origin is the difference in the steric part of the interaction energies. © 1994 by John Wiley & Sons, Inc.

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Nonempirical calculations on hydrogen-bonded and stacked structures of p-benzoquinone—hydroquinone pyridine—pyrrole and pyridine-phenol complexes

Cited by 8 publications

References 17 publications

Intermolecular Interactions in p-Chlorobenzoic Acid Dimers

Intermolecular Interactions in p-Chlorobenzoic Acid Dimers

Internal and External Implications of the Structure of Hydrogen Bonded Complexes . Ii. Mndo‐pm3 Studies on the Structure of the 4‐methylpyridine Complex With Pentachlorophenol

Decomposition analyses of the intermolecular interaction energies in two ππ stacking complexes: Quinhydrone and N,N,N′, N′‐tetramethyl‐P‐diaminobenzene‐chloranil complex

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