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      Silicon–silicon π single bond

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          Abstract

          A carbon–carbon double bond consists of a σ bond and a π bond. Recently, the concept of a π single bond, where a π bond is not accompanied by a σ bond, has been proposed in diradicals containing carbon and heteroatom radical centers. Here we report a closed-shell compound having a silicon–silicon π single bond. 1,2,2,3,4,4-Hexa- tert-butylbicyclo[1.1.0]tetrasilane has a silicon−silicon π single bond between the bridgehead silicon atoms. The X-ray crystallographic analysis shows that the silicon−silicon π single bond (2.853(1) Å) is far longer than the longest silicon−silicon bond so far reported. In spite of this unusually long bond length, the electrons of the 3p orbitals are paired, which is confirmed by measurement of electron paramagnetic resonance, and magnetic susceptibility and natural bond orbital analysis. The properties of the silicon−silicon π single bond are studied by UV/Vis and 29Si NMR spectroscopy, and theoretical calculations.

          Abstract

          Examples of π single bonds in diradicals are rare, as they are typically unstable. Here, the authors describe a room temperature-stable closed-shell bicyclic tetrasilane that features a Si-Si π single bond between two of the non-adjacent Si centers.

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          Most cited references 40

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          Pi-bonding and the lone pair effect in multiple bonds involving heavier main group elements: developments in the new millennium.

           P. Power,  C. Fischer (2010)
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            Diradicals.

             Manabu Abe (2013)
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              Tetramesityldisilene, a stable compound containing a silicon-silicon double bond.

              Irradiation of 2,2-bis(2,4,6-trimethylphenyl)hexamethyltrisilane in hydrocarbon solution produces tetramesityldisilene, which can be isolated as a yellow-orange solid stable to room temperature and above in the absence of air. Like the olefins of carbon chemistry, tetramesityldisilene undergoes addition reactions across the silicon-silicon double bond.
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                Author and article information

                Contributors
                kyushin@gunma-u.ac.jp
                ishida@tohoku.ac.jp
                hmatumoto@gunma-u.ac.jp
                Journal
                Nat Commun
                Nat Commun
                Nature Communications
                Nature Publishing Group UK (London )
                2041-1723
                11 August 2020
                11 August 2020
                2020
                : 11
                Affiliations
                [1 ]GRID grid.256642.1, ISNI 0000 0000 9269 4097, Division of Molecular Science, Graduate School of Science and Technology, , Gunma University, ; Kiryu, Gunma 376-8515 Japan
                [2 ]GRID grid.69566.3a, ISNI 0000 0001 2248 6943, Department of Chemistry, Graduate School of Science, , Tohoku University, ; Sendai, 980-8578 Japan
                [3 ]GRID grid.256642.1, ISNI 0000 0000 9269 4097, Division of Pure and Applied Science, Graduate School of Science and Technology, , Gunma University, ; Maebashi, Gunma 371-0044 Japan
                Article
                17815
                10.1038/s41467-020-17815-z
                7419521
                32782244
                © The Author(s) 2020

                Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

                Funding
                Funded by: FundRef https://doi.org/10.13039/501100001691, MEXT | Japan Society for the Promotion of Science (JSPS);
                Award ID: 18655011
                Award ID: 19350018
                Award Recipient :
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                © The Author(s) 2020

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                chemical bonding, stereochemistry

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