Preparation of donor–acceptor substituted fluorostilbenes and crystal chemistry of fluorinated (E)-4-(4-halogeno-styryl)-benzonitriles

Mariaca, Raúl; Labat, Gaël; Behrnd, N.-R.; Bonin, Michel; Helbling, Fabien; Eggli, Patrick; Couderc, Gaëtan; Neels, Antonia; Stœckli-Evans, Helen; Hulliger, Jürg

doi:10.1016/j.jfluchem.2008.09.012

Cited by 13 publications

(10 citation statements)

References 30 publications

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“…Therefore the quinone is simultaneously involved in both X‐bonding and lp–π interactions, which are important in the solid‐state architecture of this molecule. The second structure that we selected is a trans ‐stilbene‐based compound (QOSCAD,34 see Figure 3) that has iodo and cyano substituents strategically positioned to form an infinite 1D molecular chain dominated by CN ⋅⋅⋅ I contacts (3.042 Å and 172.5°). These infinite 1D chains form a 2D layer by means (among others) of lp–π contacts between the iodine atom and the electron‐deficient tetrafluorobenzonitrile ring (3.732 Å).…”

Section: Resultsmentioning

confidence: 99%

Theoretical Study on Cooperativity Effects between Anion–π and Halogen‐Bonding Interactions

et al. 2011

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This article analyzes the interplay between lone pair-π (lp-π) or anion-π interactions and halogen-bonding interactions. Interesting cooperativity effects are observed when lp/anion-π and halogen-bonding interactions coexist in the same complex, and they are found even in systems in which the distance between the anion and halogen-bond donor molecule is longer than 9 Å. These effects are studied theoretically in terms of energetic and geometric features of the complexes, which are computed by ab initio methods. Bader's theory of "atoms in molecules" is used to characterize the interactions and to analyze their strengthening or weakening depending upon the variation of charge density at critical points. The physical nature of the interactions and cooperativity effects are studied by means of molecular interaction potential with polarization partition scheme. By taking advantage of all aforementioned computational methods, the present study examines how these interactions mutually influence each other. Additionally, experimental evidence for such interactions is obtained from the Cambridge Structural Database (CSD).

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Section: Resultsmentioning

confidence: 99%

Theoretical Study on Cooperativity Effects between Anion–π and Halogen‐Bonding Interactions

et al. 2011

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“…A recent study by Mariaca et al 14,36 has shown the influence of fluorination on the crystal packing of donor-acceptor substituted stilbenes. A series of substituted halogeno-cyanostilbenes (Fig.…”

Section: Effect Of Exchange Of H Vs F (Complete or Partial Exchange)mentioning

confidence: 99%

Organic fluorine compounds: a great opportunity for enhanced materials properties

et al. 2011

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Interactions of "organic fluorine" have gained great interest not only in the context of crystal engineering, but also in the systematic design of functional materials. The first part of this tutorial review presents an overview on interactions known by organic fluorine. This involves π-π(F), C-F···H, F···F, C-F···π(F), C-F···π, C-F···M(+), C-F···C=O and anion-π(F) interactions, as well as other halogen bonds. The effect of the exchange of H vs. F is discussed by means of several examples and a short introduction to the young field of "fluorous" chemistry is given. The second part is dedicated to numerous applications of fluorine and fluorous interactions. It is shown how application of fluorination is used to enable a number of reactions, to improve materials properties and even open up new fields of research.

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“…[14] and references therein). As in the case of substituted stilbenes, already partial substitution can alter the crystal packing dramatically [14b,c] . However, under the isolated conditions of the gas phase, free of packing effects, there are fewer examples of this type of exchange and its effects.…”

Section: Figurementioning

confidence: 99%

Do Docking Sites Persist Upon Fluorination? The Diadamantyl Ether‐Aromatics Challenge for Rotational Spectroscopy and Theory

Quesada‐Moreno

Pinacho

Pérez

et al. 2021

Chemistry A European J

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Fluorinated derivatives of biological molecules have proven to be highly efficient at modifying the biological activity of a given protein through changes in the stability and the kind of docking interactions. These interactions can be hindered or facilitated based on the hydrophilic/hydrophobic character of a particular protein region. Diadamantyl ether (C20H30O) possesses both kinds of docking sites, serving as a good template to model these important contacts with aromatic fluorinated counterparts. In this work, an experimental study on the structures of several complexes between diadamantyl ether and benzene as well as a series of fluorinated benzenes is reported to analyze the effect of H→F substitution on the interaction and structure of the resulting molecular clusters using rotational spectroscopy. All experimentally observed complexes are largely dominated by London dispersion interactions with the hydrogen‐terminated surface areas of diadamantyl ether. Already single substitution of one hydrogen atom with fluorine changes the preferred docking site of the complexes. However, the overall contributions of the different intermolecular interactions are similar for the different complexes, contrary to previous studies focusing on the difference in interactions using fluorinated and non‐fluorinated molecules.

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Preparation of donor–acceptor substituted fluorostilbenes and crystal chemistry of fluorinated (E)-4-(4-halogeno-styryl)-benzonitriles

Cited by 13 publications

References 30 publications

Theoretical Study on Cooperativity Effects between Anion–π and Halogen‐Bonding Interactions

Theoretical Study on Cooperativity Effects between Anion–π and Halogen‐Bonding Interactions

Organic fluorine compounds: a great opportunity for enhanced materials properties

Do Docking Sites Persist Upon Fluorination? The Diadamantyl Ether‐Aromatics Challenge for Rotational Spectroscopy and Theory

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