Aromatic interactions

Hunter, Christopher A.; Lawson, Kevin R.; Perkins, Julie; Urch, Christopher J.

doi:10.1039/b008495f

Cited by 1,354 publications

(1,140 citation statements)

References 72 publications

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“…It has been proposed that such offset stacking maximises the electrostatic attraction between coplanar aromatic systems. 12 The distances between the meanplanes in the structures of 6, 7 and 8 are 3.398(5), 3.410(4) and 3.428(3) Å, respectively, which are similar to the distance between the planes of carbon atoms in graphite (3.35Å). The γ-herringbone pattern also allows edge-toface interactions to occur between molecules of adjacent stacks.…”

Section: Introductionmentioning

confidence: 55%

“…Since each of these compounds is also capable of acting as a chelating and/or bridging ligand, this study is also likely to be of interest to chemists studying the coordination and supramolecular chemistry of such ligands. The seven biheterocycles studied (6)(7)(8)(9)(10)(11)(12) were prepared by literature procedures and chosen for their ability to test the factors discussed above. Each could potentially exist in two planar conformations of different symmetry.…”

Section: Introductionmentioning

confidence: 99%

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Solid state conformations of symmetrical aromatic biheterocycles: an X-ray crystallographic investigation

2005

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Accurate, low temperature X-ray crystal structure determinations show that 3,3 -biquinoline (6), 2,2 -biquinazoline (7), 2,2 -biquinoxaline (8), 2,2 -bibenzoxazole (10) and 2,2 -bibenzothiazole (11) all exist in the solid state in centrosymmetric, planar conformations that minimise their dipole moments and maximise both conjugation between the rings and various types of attractive intermolecular associations. In contrast, 4,4 -biquinazoline ( 9) and 1,1 -bibenzotriazole (12) display non-planar conformations due to repulsive intramolecular interactions.

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Section: Introductionmentioning

confidence: 55%

Section: Introductionmentioning

confidence: 99%

Solid state conformations of symmetrical aromatic biheterocycles: an X-ray crystallographic investigation

2005

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“…Positive values of R 2 (2) indicate that the functional group is moving away from the center of the hexafluorobenzene ring and negative values of R 2 (3) indicate that the functional group is moving towards the center of the hexafluorobenzene ring. A distance of 0.0 Å is, therefore, for a sandwich complex (4).…”

Section: Computational Resultsmentioning

confidence: 99%

“…(2), where a,b, and c are adjustable constants, L is the van der Waals contact distance between the two arenes. (2) Thus the new functional model includes a term for charge-transfer interaction in addition to the repulsive and the London force terms in the Lennard-Jones equation.…”

Section: Distance Dependence Of Interaction Energy At Short Contacmentioning

confidence: 99%

Substituent Effects in C₆F₆C₆H₅X Stacking Interactions

2006

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Parallel displaced and sandwich configurations of hexafluorobenzene-substituted benzene dimers are studied by ab initio molecular orbital methods up to the MP2(full)/aug-cc-pVDZ level of theory to reveal how substituents influence π-π interactions. Two minimum energy configurations are found, one with the substituent group away from (2a-2f) and the other with the substituent group on top of the π-face of the hexafluorobenzene (3a-3f). Higher binding energies are predicted for dimers with the substituent on the π-face (3a-3f). All sandwich dimers (4a-4e) are found to be saddle points on the potential energy surfaces. A parallel displaced minimum energy configuration is also predicted for the parent complex, C 6 F 6 -C 6 H 6 , which is in contrast to predictions based on quadrupole moments of benzene and hexafuorobenzene. The preference for the parallel displaced, rather than the sandwich configuration, is rationalized based on the smaller interplanar distance in the former. The closeness of contact in the parallel displaced dimers leads to greater binding energies. The shape of the electron density isosurface of the monomers is suggested to provide a guide for the prediction of how arenes stack with one another. A large difference in binding energy between the C 6 F 6 complex of aniline (3e) and N,N-dimethylaniline (3f) is calculated and charge-transfer interactions are suggested to play a role in the latter.

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“…Aromatic-aromatic or p-p stacking interactions are well known as effective noncovalent intermolecular forces, which are normally employed for H-type or J-type stacking of aromatic groups with ring centroid-centroid distances of B3.3-3.8 Å [25][26][27] . In particular, they can facilitate self-assembly or molecular recognition processes while involving extended structures that are constructed from building blocks with aromatic moieties to matching MFI nanosheet 28,29 .…”

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confidence: 99%

π–π interaction of aromatic groups in amphiphilic molecules directing for single-crystalline mesostructured zeolite nanosheets

et al. 2014

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One of the challenges in material science has been to prepare macro-or mesoporous zeolite. Although examples of their synthesis exist, there is a need for a facile yet versatile approach to such hierarchical structures. Here we report a concept for designing a single quaternary ammonium head amphiphilic template with strong ordered self-assembling ability through p-p stacking in hydrophobic side, which stabilizes the mesostructure to form singlecrystalline mesostructured zeolite nanosheets. The concept is demonstrated for the formation of a new type of MFI (zeolite framework code by International Zeolite Association) nanosheets joined with a 90°rotational boundary, which results in a mesoporous zeolite with highly specific surface area even after calcination. Low binding energies for this selfassembling system are supported by a theoretical analysis. A geometrical matching between the arrangement of aromatic groups and the zeolitic framework is speculated for the formation of single-crystalline MFI nanosheets.

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Aromatic interactions

Cited by 1,354 publications

References 72 publications

Solid state conformations of symmetrical aromatic biheterocycles: an X-ray crystallographic investigation

Solid state conformations of symmetrical aromatic biheterocycles: an X-ray crystallographic investigation

Substituent Effects in C₆F₆C₆H₅X Stacking Interactions

π–π interaction of aromatic groups in amphiphilic molecules directing for single-crystalline mesostructured zeolite nanosheets

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Aromatic interactions

Cited by 1,354 publications

References 72 publications

Solid state conformations of symmetrical aromatic biheterocycles: an X-ray crystallographic investigation

Solid state conformations of symmetrical aromatic biheterocycles: an X-ray crystallographic investigation

Substituent Effects in C6F6C6H5X Stacking Interactions

π–π interaction of aromatic groups in amphiphilic molecules directing for single-crystalline mesostructured zeolite nanosheets

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Substituent Effects in C₆F₆C₆H₅X Stacking Interactions