London Dispersion Enables the Shortest Intermolecular Hydrocarbon H···H Contact

Journal of the American Chemical Society
Sören RöselPeter R Schreiner

Abstract

Neutron diffraction of tri(3,5-tert-butylphenyl)methane at 20 K reveals an intermolecular C-H···H-C distance of only 1.566(5) Å, which is the shortest reported to date. The compound crystallizes as a C3-symmetric dimer in an unusual head-to-head fashion. Quantum chemical computations of the solid state at the HSE-3c level of theory reproduce the structure and the close contact well (1.555 Å at 0 K) and emphasize the significance of packing effects; the gas-phase dimer structure at the same level shows a 1.634 Å C-H···H-C distance. Intermolecular London dispersion interactions between contacting tert-butyl substituents surrounding the central contact deliver the decisive energetic contributions to enable this remarkable bonding situation.

References

Nov 13, 2004·Journal of the American Chemical Society·Tinh-Alfredo V KhuongMiguel A Garcia-Garibay
Jan 17, 2007·Angewandte Chemie·Björn O RoosLaura Gagliardi
Jan 31, 2007·Journal of the American Chemical Society·Gregory C Welch, Douglas W Stephan
Dec 17, 2008·Angewandte Chemie·Wei WuPhilippe C Hiberty
Jul 10, 2009·The Journal of Chemical Physics·Peifeng Su, Hui Li
Mar 30, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Stefan GrimmeStephan Ehrlich
Apr 26, 2011·Journal of Chemical Theory and Computation·Julia Contreras-GarcíaWeitao Yang
Oct 26, 2011·Angewandte Chemie·Stefan Grimme, Peter R Schreiner
Feb 23, 2012·Nature Chemistry·Sason ShaikPhilippe C Hiberty
Jul 28, 2012·Journal of the American Chemical Society·Andrey A FokinPeter R Schreiner
May 2, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Santiago Alvarez
Aug 27, 2013·Journal of the American Chemical Society·Jie ZongRobert A Pascal
Dec 4, 2013·Physical Chemistry Chemical Physics : PCCP·Laura BerstisKim K Baldridge
Aug 12, 2015·Angewandte Chemie·J Philipp Wagner, Peter R Schreiner
Nov 26, 2015·Journal of Chemical Theory and Computation·J Philipp Wagner, Peter R Schreiner
Nov 28, 2015·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Rohoullah Firouzi, Shant Shahbazian
Apr 15, 2016·Chemical Reviews·Stefan GrimmeChristoph Bannwarth
Jun 1, 2016·Physical Chemistry Chemical Physics : PCCP·Jan Gerit BrandenburgStefan Grimme
Aug 25, 2016·Chemistry : a European Journal·Martin RahmN W Ashcroft
Jan 6, 2017·The Journal of Physical Chemistry. B·Nilangshu MandalAyan Datta

❮ Previous
Next ❯

Citations

Nov 7, 2017·Angewandte Chemie·Stefan Grimme, Peter R Schreiner
Mar 24, 2018·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Arpita VaradwajKoichi Yamashita
Apr 11, 2018·Journal of Physics. Condensed Matter : an Institute of Physics Journal·Eike Caldeweyher, Jan Gerit Brandenburg
Aug 1, 2018·Physical Chemistry Chemical Physics : PCCP·Nisha MehtaLars Goerigk
Aug 29, 2018·Chemistry : a European Journal·Dominik LungerichNorbert Jux
Jul 27, 2018·Journal of Biomolecular Structure & Dynamics·Ol'ha O Brovarets', Dmytro M Hovorun
May 21, 2019·Angewandte Chemie·Robert Pollice, Peter Chen
Jul 18, 2018·Beilstein Journal of Organic Chemistry·Eric DetmarMartin Breugst
Jul 7, 2018·Beilstein Journal of Organic Chemistry·Tim GouldSherif Abdulkader Tawfik
Jul 18, 2018·Beilstein Journal of Organic Chemistry·Ganna Gryn'ova, Clémence Corminboeuf
Dec 18, 2019·Chemistry : a European Journal·Michael RuppelNorbert Jux
Feb 15, 2020·Journal of Computational Chemistry·José Luis Casals-SainzÁngel Martín Pendás
Aug 8, 2017·Journal of Computational Chemistry·Oinam Romesh Meitei, Andreas Heßelmann
Jun 24, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Ina ØstrømRenato L T Parreira
Jun 30, 2019·Luminescence : the Journal of Biological and Chemical Luminescence·Hazem AmarneSuning Wang
Jan 27, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Arpita VaradwajPradeep R Varadwaj
Apr 25, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Thomas R CundariPeter T Wolczanski
Sep 22, 2020·Faraday Discussions·L DonàB Civalleri
Oct 2, 2020·Angewandte Chemie·Marcel A Strauss, Hermann A Wegner
Nov 20, 2020·Chemical Communications : Chem Comm·Nilangshu Mandal, Ayan Datta
Nov 15, 2020·Nature Communications·Bartomeu MonserratBingqing Cheng
Apr 22, 2021·Journal of Chemical Theory and Computation·Nisha MehtaLars Goerigk
Oct 3, 2019·The Journal of Chemical Physics·L DonáB Civalleri
Jun 29, 2021·Chemical Communications : Chem Comm·Alfonso García-MárquezRafael Gramage-Doria
Jul 9, 2021·The Journal of Physical Chemistry. a·Martin-Louis Y RiuChristopher C Cummins
Apr 17, 2018·The Journal of Organic Chemistry·Ina ØstrømRenato L T Parreira
Aug 26, 2017·The Journal of Physical Chemistry Letters·Jan Gerit BrandenburgSimon R Hall
Oct 27, 2017·Journal of the American Chemical Society·David Van CraenMarkus Albrecht
Jul 18, 2019·The Journal of Physical Chemistry. a·Dominique A Wappett, Lars Goerigk
Oct 6, 2018·Journal of the American Chemical Society·Sören RöselPeter R Schreiner
Dec 1, 2021·Journal of the American Chemical Society·Ephrath SolelPeter R Schreiner

❮ 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.