Pyramidanes
- Vladimir Ya. Lee ,
- Yuki Ito ,
- Akira Sekiguchi ,
- Heinz Gornitzka ,
- Olga A. Gapurenko ,
- Vladimir I. Minkin , and
- Ruslan M. Minyaev
View Author Information
† Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
‡ CNRS, LCC, Université de Toulouse, UPS, INPT, 205 route de Narbonne, BP 44099, F-31077 Toulouse Cedex 4, France
§ Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki ave., Rostov-on-Don 344090, Russian Federation
Abstract
Pyramidane is an elusive but highly desirable target for synthetic chemists that has attracted a great deal of attention because of its nonclassical structure and unusual bonding features. Although well studied on theoretical grounds, neither the parent all-carbon pyramidane nor its derivatives containing heavier group 14 elements have ever been isolated and characterized. In this Communication, we report on the synthesis and structural elucidation of the first stable representatives of this class of highly strained polyhedral compounds: germa- and stannapyramidanes Ge[C4(SiMe3)4] and Sn[C4(SiMe3)4]. The peculiar structural and bonding features of these compounds are verified by combined experimental and computational analyses, showing these derivatives to be nonclassical neutral compounds with a very large contribution of ionic character.
Cited By
This article is cited by 29 publications.
- Tobias Heitkemper, Julijan Sarcevic, Christian P. Sindlinger. A Neutral Silicon(II) Half-Sandwich Compound. Journal of the American Chemical Society 2020, 142 (51) , 21304-21309. https://doi.org/10.1021/jacs.0c11904
- Vladimir Ya. Lee, Haruka Sugasawa, Olga A. Gapurenko, Ruslan M. Minyaev, Vladimir I. Minkin, Heinz Gornitzka, Akira Sekiguchi. From Borapyramidane to Borole Dianion. Journal of the American Chemical Society 2018, 140 (19) , 6053-6056. https://doi.org/10.1021/jacs.8b03473
- Masaichi Saito . Transition-Metal Complexes Featuring Dianionic Heavy Group 14 Element Aromatic Ligands. Accounts of Chemical Research 2018, 51 (1) , 160-169. https://doi.org/10.1021/acs.accounts.7b00367
- Vladimir Ya. Lee, Kei Ota, Yuki Ito, Olga A. Gapurenko, Akira Sekiguchi, Ruslan M. Minyaev, Vladimir I. Minkin, and Heinz Gornitzka . Bis(stibahousene). Journal of the American Chemical Society 2017, 139 (39) , 13897-13902. https://doi.org/10.1021/jacs.7b07712
- Takuya Kuwabara, Marisa Nakada, Jumpei Hamada, Jing Dong Guo, Shigeru Nagase, and Masaichi Saito . (η4-Butadiene)Sn(0) Complexes: A New Approach for Zero-Valent p-Block Elements Utilizing a Butadiene as a 4π-Electron Donor. Journal of the American Chemical Society 2016, 138 (35) , 11378-11382. https://doi.org/10.1021/jacs.6b07304
- Robert Sedlak, Olga A. Stasyuk, Célia Fonseca Guerra, Jan Řezáč, Aleš Růžička, and Pavel Hobza . New Insight into the Nature of Bonding in the Dimers of Lappert’s Stannylene and Its Ge Analogs: A Quantum Mechanical Study. Journal of Chemical Theory and Computation 2016, 12 (4) , 1696-1704. https://doi.org/10.1021/acs.jctc.6b00065
- Vladimir Ya. Lee, Olga A. Gapurenko, Yuki Ito, Takahiko Meguro, Haruka Sugasawa, Akira Sekiguchi, Ruslan M. Minyaev, Vladimir I. Minkin, Rolfe H. Herber, and Heinz Gornitzka . Pyramidanes: The Covalent Form of the Ionic Compounds. Organometallics 2016, 35 (3) , 346-356. https://doi.org/10.1021/acs.organomet.5b00924
- Kseniya V. Tsys, Maxim G. Chegerev, Georgy K. Fukin, Andrey G. Starikov, Alexandr V. Piskunov. Low-valent oligogermanium amidophenolate complex comprising a unique Ge4 chain. Mendeleev Communications 2020, 30 (2) , 205-208. https://doi.org/10.1016/j.mencom.2020.03.025
- Denis Sabirov, Kamila Koledina, . Classification of isentropic molecules in terms of Shannon entropy. EPJ Web of Conferences 2020, 244 , 01016. https://doi.org/10.1051/epjconf/202024401016
- Olga A. Gapurenko, Vladimir Ya. Lee, Ruslan M. Minyaev, Vladimir I. Minkin. Theoretical Prediction for Synthetic Realization: Pyramidal Systems ClE[E′ 4 R 4 ] (E = B–Ga, E′ = C–Ge, R = SiMe 3 , SiMe t Bu 2 ): A DFT Study. Heteroatom Chemistry 2019, 2019 , 1-6. https://doi.org/10.1155/2019/3659287
- Olga A. Gapurenko, Ruslan M. Minyaev, Nikita S. Fedik, Vitaliy V. Koval, Alexander I. Boldyrev, Vladimir I. Minkin. Structure and bonding of new boron and carbon superpolyhedra. Structural Chemistry 2019, 30 (3) , 805-814. https://doi.org/10.1007/s11224-019-1279-5
- Yunus E. Türkmen. Three-Membered Rings with One Silicon, Germanium, Tin or Lead Atom. 2019,,https://doi.org/10.1016/B978-0-12-409547-2.14787-0
- . Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. 2019,,https://doi.org/
- Paresh Kumar Majhi, Takahiro Sasamori. Tetrylones: An Intriguing Class of Monoatomic Zero-valent Group 14 Compounds. Chemistry - A European Journal 2018, 24 (38) , 9441-9455. https://doi.org/10.1002/chem.201800142
- Olga A. Gapurenko, Vladimir Ya. Lee, Ruslan M. Minyaev, Vladimir I. Minkin, Akira Sekiguchi. Hybrid group 15(E 15 )–group 14(E 14 ) element cationic pyramidal structures E 15 [E 14 4 (SiR 3 ) 4 ] + : A DFT study. Tetrahedron Letters 2017, 58 (21) , 2054-2057. https://doi.org/10.1016/j.tetlet.2017.04.040
- Larissa A. Leites, Rinat R. Aysin, Sergey S. Bukalov, Vladimir Ya. Lee, Hakura Sugasawa, Akira Sekiguchi. The study of bonding in pyramidanes [(Me3Si)4C4]E (E = Ge, Sn, Pb) by optical (Raman, UV–vis) spectroscopy and quantum-chemical methods. Journal of Molecular Structure 2017, 1130 , 775-780. https://doi.org/10.1016/j.molstruc.2016.11.001
- Olga A. Gapurenko, Ruslan M. Minyaev, Vladimir I. Minkin. Nonclassical Organosilicon Compounds. 2017,,, 3-24. https://doi.org/10.1016/B978-0-12-801981-8.00001-0
- . Organosilicon Compounds. 2017,,https://doi.org/
- Dong Fan, Shaohua Lu, Yundong Guo, Xiaojun Hu. Novel bonding patterns and optoelectronic properties of the two-dimensional Si x C y monolayers. Journal of Materials Chemistry C 2017, 5 (14) , 3561-3567. https://doi.org/10.1039/C6TC05415C
- Kori D. McDonald, Evelyn O. Ojo, Joel F. Liebman. What Are the Structures of the Octet Rule Obeying All-Carbon Species Cx (2 ≤ x ≤ 7 and Larger x)?. 2017,,, 1-45. https://doi.org/10.4018/978-1-5225-0492-4.ch001
- , . Sustainable Nanosystems Development, Properties, and Applications. 2017,,https://doi.org/10.4018/978-1-5225-0492-4
- Vladimir Ya. Lee, Haruka Sugasawa, Olga A. Gapurenko, Ruslan M. Minyaev, Vladimir I. Minkin, Heinz Gornitzka, Akira Sekiguchi. A Cationic Phosphapyramidane. Chemistry - A European Journal 2016, 22 (49) , 17585-17589. https://doi.org/10.1002/chem.201604480
- Errol G. Lewars. Selected Literature Highlights, Books, Websites, Software and Hardware. 2016,,, 613-643. https://doi.org/10.1007/978-3-319-30916-3_9
- Errol G. Lewars. Computational Chemistry. 2016,,https://doi.org/10.1007/978-3-319-30916-3
- Mikhail M. Levitsky, Alexey N. Bilyachenko. Modern concepts and methods in the chemistry of polyhedral metallasiloxanes. Coordination Chemistry Reviews 2016, 306 , 235-269. https://doi.org/10.1016/j.ccr.2015.07.007
- Vladimir Ya. Lee, Yuki Ito, Olga A. Gapurenko, Akira Sekiguchi, Vladimir I. Minkin, Ruslan M. Minyaev, Heinz Gornitzka. Pentagermapyramidane: Crystallizing the “Transition-State” Structure. Angewandte Chemie 2015, 127 (19) , 5746-5749. https://doi.org/10.1002/ange.201500731
- Vladimir Ya. Lee, Yuki Ito, Olga A. Gapurenko, Akira Sekiguchi, Vladimir I. Minkin, Ruslan M. Minyaev, Heinz Gornitzka. Pentagermapyramidane: Crystallizing the “Transition-State” Structure. Angewandte Chemie International Edition 2015, 54 (19) , 5654-5657. https://doi.org/10.1002/anie.201500731
- Vladimir Ya. Lee, Akira Sekiguchi. 1,1-Dilithiosilanes, 1,1-dilithiogermanes, 1,1-dilithiostannanes and related compounds: Organometallic reagents of the new generation. Mendeleev Communications 2015, 25 (3) , 161-167. https://doi.org/10.1016/j.mencom.2015.05.001
- . Anorganische Chemie 2013. Nachrichten aus der Chemie 2014,,, 219-236. https://doi.org/10.1002/nadc.201490083