X-ray diffraction and theoretical studies for the quantitative assessment of intermolecular arene-perfluoroarene stacking interactions

Chemistry : a European Journal
Sergio BacchiAngelo Gavezzotti

Abstract

The arene-perfluoroarene stacking interaction was studied by experimental and theoretical methods. A series of compounds with different possibilities for formation of this recognition motif in the solid state were synthesized, and their crystal structures determined by single-crystal X-ray diffraction. The crystal packing of these compounds, as well as the packing of related compounds retrieved from crystallographic databases, were analyzed with quantitative crystal potentials: total lattice energies and the cohesive energies of closest molecular pairs in the crystals were calculated. The arene-perfluoroarene recognition motif emerges as a dominant interaction in the non-hydrogen-bonding compounds studied here, to the point that asymmetric dimers formed over the stacking motif carry over to asymmetric units made of two molecules in the crystal both for pure compounds and for molecular complexes; however, inter-ring distances and angles range from 3.70 to 4.85 A and from 5 to 21 degrees , respectively. Pixel energy partitioning reveals that whenever aromatic rings stack, the largest cohesive energy contribution comes from dispersion, which roughly amounts to 20 kJ mol(-1) per phenyl ring, while the coulombic term is minor but si...Continue Reading

References

Sep 19, 2001·Chemistry : a European Journal·H AdamsJ G Vinter
Jul 12, 1996·The Journal of Organic Chemistry·Richard E. GillardDavid J. Williams
Oct 9, 2002·Angewandte Chemie·Gérald Mathis, Jürg Hunziker
Sep 5, 2002·Journal of the American Chemical Society·Mutasem Omar SinnokrotC David Sherrill
Oct 26, 2002·Chemical Communications : Chem Comm·Kathryn A Frey, Stephen A Woski
Dec 20, 2002·Chemistry : a European Journal·Gianni ChessariCristiano Zonta
Mar 20, 2003·Angewandte Chemie·Emmanuel A MeyerFrançois Diederich
Aug 7, 2003·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Siwaporn MeejooKenneth D Harris
Jan 12, 2005·Chemical Society Reviews·Katharina ReichenbächerJurg Hulliger
Jul 21, 2006·The Journal of Physical Chemistry. B·P Maarten Biesheuvel, Alexander Wittemann

❮ Previous
Next ❯

Citations

Mar 17, 2011·The Journal of Chemical Physics·A HinderhoferF Schreiber
Jan 17, 2012·Journal of Pharmaceutical Sciences·Ganesaratnam K BalendiranNigam P Rath
May 5, 2017·Acta Crystallographica. Section C, Structural Chemistry·Ya Jie KongShuang Yin
May 4, 2011·Angewandte Chemie·Laura M SalonenFrançois Diederich
Jan 31, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Alexander Hinderhofer, Frank Schreiber
Sep 20, 2008·Chemical Communications : Chem Comm·Ami DoshiFrieder Jäkle
Aug 4, 2010·Angewandte Chemie·Hong Zheng, Jianmin Gao
Mar 31, 2011·Chemical Society Reviews·Ricarda BergerJürg Hulliger
Aug 27, 2009·Organic & Biomolecular Chemistry·Gian Maria Dell'AnnaStefano Roelens
Jul 26, 2008·Journal of the American Chemical Society·Rui XuHolger Frauenrath
Jun 20, 2020·Inorganic Chemistry·Guillermo Moreno-AlcántarHugo Torrens
Dec 20, 2007·Journal of the American Chemical Society·Tanmoy DuttaMark D Watson
Jun 21, 2007·Journal of the American Chemical Society·Angiolina ComottiPiero Sozzani

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.