Parallel alignment of water and aryl rings—crystallographic and theoretical evidence for the interaction

Ostojić, Bojana; Janjić, Goran V.; Zarić, Snežana D.

doi:10.1039/b812925h

Cited by 47 publications

(34 citation statements)

References 31 publications

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“…[30] However, this distance is significantly longer than that found for the tetrasodium salt and indicates that the water molecule is not pushed into the cavity as forcefully. The distance of the second interacting oxygen atom (O21) to the corresponding aryl plane is 3.26 ; however, the normal is further from the centroid of the ring and thus this value is not directly comparable to the other oxygen-aryl distances.…”

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confidence: 90%

“…Another major factor in the difference of hydrogen-bond energies is the geometry of the bond, as shown for the interaction of water with benzene, [30,31] phenol [32] or graphite. [33] In the interaction of water with benzene, the optimal distance between water oxygen and aromatic ring plane ranges between 3.44 and 3.57 depending on the computational method applied.…”

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confidence: 99%

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The Structure of Water in p‐Sulfonatocalix[4]arene

Fucke

Anderson

Filby

et al. 2011

Chemistry A European J

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Tetrasodium p-sulfonatocalix[4]arene exists as a hydrate with approximately 14 water molecules and has three polymorphic modifications, all of which contain a water molecule in the molecular cavity that is engaged in OH···π interactions. Single-crystal neutron structures are reported for two of these three forms and reveal a "compressed" water molecule with short OH bonds. Partial atomic charges and hardness analysis (PACHA) calculations based on the neutron coordinates give an OH···π interaction energy of 6.9-7.5 kJ mol(-1). The PACHA analysis also reveals the dominance of the charge-assisted hydrogen bonds from the Na(+)-coordinated water molecules. The instability of the crystal towards dehydration can be traced to an uncoordinated lattice water site. The remarkable calixarene-Na(+)-hydrate motif is conserved almost unchanged across all three polymorphs. A single-crystal neutron structure is also reported for pentasodium p-sulfonatocalix[4]arene·12H(2)O, which exhibits an intracavity water molecule that is engaged in both OH···π and OH···O hydrogen bonding. The shorter covalent bond to the hydrogen atom that forms the interaction with the aromatic ring is again apparent.

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confidence: 90%

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confidence: 99%

The Structure of Water in p‐Sulfonatocalix[4]arene

Fucke

Anderson

Filby

et al. 2011

Chemistry A European J

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“…One of the most important characteristics of water is its ability to form hydrogen bonds to other molecules, including other water molecules. There have been numerous studies of its interactions with ions, molecules, and interfaces . These suggest, for example, that changes in the structure of liquid water due to ions involve more than just the first hydration shell…”

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confidence: 99%

Hydrogen Bonding between Metal‐Ion Complexes and Noncoordinated Water: Electrostatic Potentials and Interaction Energies

Andrić¹,

Misini-Ignjatović

Murray

et al. 2016

ChemPhysChem

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The hydrogen bonding of noncoordinated water molecules to each other and to water molecules that are coordinated to metal-ion complexes has been investigated by means of a search of the Cambridge Structural Database (CSD) and through quantum chemical calculations. Tetrahedral and octahedral complexes that were both charged and neutral were studied. A general conclusion is that hydrogen bonds between noncoordinated water and coordinated water are much stronger than those between noncoordinated waters, whereas hydrogen bonds of water molecule in tetrahedral complexes are stronger than in octahedral complexes. We examined the possibility of correlating the computed interaction energies with the most positive electrostatic potentials on the interacting hydrogen atoms prior to interaction and obtained very good correlation. This study illustrates the fact that electrostatic potentials computed for ground-state molecules, prior to interaction, can provide considerable insight into the interactions.

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“…In spite of extensive studies on benzene–benzene interactions,2, 3 no studies on stacking interactions with large horizontal displacement have been performed. Our recent results reveal that the parallel alignment on water–aromatic interactions can be significantly strong at large horizontal displacements 5. This prompted us to study benzene–benzene interactions at large horizontal displacements.…”

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confidence: 95%

“…Herein, we present our result on the interactions of two benzene molecules in the parallel orientation. Since analysis of the data in the crystal structures from the Cambridge Structural Database (CSD) enable the study of noncovalent interactions,5, 6 our analysis is based on crystal structures from the CSD. We also performed DFT and CCSD(T) calculations.…”

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confidence: 99%