logo

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2002, 124, 33, 9865-9869
RETURN TO ISSUEPREVArticleNEXT

Isolable Silyl and Germyl Radicals Lacking Conjugation with π-Bonds:  Synthesis, Characterization, and Reactivity

View Author Information
Contribution from the Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
Cite this: J. Am. Chem. Soc. 2002, 124, 33, 9865–9869
Publication Date (Web):July 27, 2002
https://doi.org/10.1021/ja0126780
Copyright © 2002 American Chemical Society
RIGHTS & PERMISSIONS
Article Views
1844
Altmetric
-
Citations
114
LEARN ABOUT THESE METRICS

Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.

Read OnlinePDF (98 KB)
Get e-Alerts
Supporting Info (2)»
SUBJECTS:

Abstract

Abstract Image

The one-electron oxidation reaction of tris[di-tert-butyl(methyl)silyl]silyl and -germyl anions with dichlorogermylene−dioxane complex results in the formation of stable tris[di-tert-butyl(methyl)silyl]silyl and -germyl radicals 1 and 2, representing the first isolable radical species of heavier Group 14 elements lacking stabilization by conjugation with π-bonds. The crystal structures of both silyl and germyl radicals 1 and 2 showed a completely planar geometry around the radical centers. The ESR spectra of 1 and 2 showed strong signals with characteristic satellites due to the coupling with the 29Si and 73Ge nuclei. The small values of the hyperfine coupling constants a(29Si) and a(73Ge) clearly indicate the π-character of both radicals, corresponding to a planar geometry and sp2 hybridization of the radical centers. Both 1 and 2 easily undergo halogenation reactions with carbon tetrachloride, 1,2-dibromoethane, and benzyl bromide to form the corresponding halosilanes and halogermanes.

*

 Author for correspondence. E-mail:  [email protected]

Supporting Information Available

ARTICLE SECTIONS
Jump To

Tables of crystallographic data including atomic positional and thermal parameters for 1 and 2 (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 138 publications.

  1. Shunya Honda, Ryutaro Sugawara, Shintaro Ishida, Takeaki Iwamoto. A Spiropentasiladiene Radical Cation: Spin and Positive Charge Delocalization across Two Perpendicular Si═Si Bonds and UV–vis–NIR Absorption in the IR-B Region. Journal of the American Chemical Society 2021, Article ASAP.
  2. Vladimir Ya. Lee, Yuki Ito, Olga A. Gapurenko, Ruslan M. Minyaev, Heinz Gornitzka, Akira Sekiguchi. From a (Silatrigerma)cyclobutenylium Ion to a (Silatrigerma)cyclobutenyl Radical and Back. Journal of the American Chemical Society 2020, 142 (38) , 16455-16460. https://doi.org/10.1021/jacs.0c08052
  3. Lizhi Tao, Ting Yi Lai, Philip P. Power, R David Britt. Germanium Hydride Radical Trapped during the Photolysis/Thermolysis of Diarylgermylene. Inorganic Chemistry 2019, 58 (22) , 15034-15038. https://doi.org/10.1021/acs.inorgchem.9b02504
  4. Soren K. Mellerup, Yunshu Cui, Felipe Fantuzzi, Paul Schmid, James T. Goettel, Guillaume Bélanger-Chabot, Merle Arrowsmith, Ivo Krummenacher, Qing Ye, Volker Engel, Bernd Engels, Holger Braunschweig. Lewis-Base Stabilization of the Parent Al(I) Hydride under Ambient Conditions. Journal of the American Chemical Society 2019, 141 (42) , 16954-16960. https://doi.org/10.1021/jacs.9b09128
  5. Jiaxiu Yu, Yingying Qin, Gengwen Tan, Huan Wang, Hecong Cheng, Wenyuan Wang, Anyang Li. Types of Six-Membered N-Heterocyclic Germanium Radicals: A Combined Computational and Experimental Study. Inorganic Chemistry 2019, 58 (9) , 5688-5694. https://doi.org/10.1021/acs.inorgchem.9b00034
  6. Shu-Hua Zhang, Emma Carter, Hong-Wei Xi, Yongxin Li, Kok Hwa Lim, and Cheuk-Wai So . Delocalized Hypervalent Silyl Radical Supported by Amidinate and Imino Substituents. Inorganic Chemistry 2017, 56 (2) , 701-704. https://doi.org/10.1021/acs.inorgchem.6b02427
  7. Naokazu Kano, Satoru Tsukada, Yusuke Shibata, Takayuki Kawashima, Hiroyasu Sato, Jing-Dong Guo, and Shigeru Nagase . Interconversion among Dianionic, Anionic, and Neutral Compounds Bearing a Bond between Two Pentacoordinated Germanium Atoms. Organometallics 2015, 34 (1) , 56-62. https://doi.org/10.1021/om500814g
  8. Hiroaki Tanaka, Masaaki Ichinohe, and Akira Sekiguchi . An Isolable NHC-Stabilized Silylene Radical Cation: Synthesis and Structural Characterization. Journal of the American Chemical Society 2012, 134 (12) , 5540-5543. https://doi.org/10.1021/ja301180v
  9. Kiera McNeice, Vladimir Ya. Lee, and Akira Sekiguchi . Making a Cyclotrigermene from a Digermene. Organometallics 2011, 30 (17) , 4796-4797. https://doi.org/10.1021/om200619v
  10. Takeshi Nozawa, Michiyo Nagata, Masaaki Ichinohe, and Akira Sekiguchi . Isolable p- and m-[(tBu2MeSi)2Si]2C6H4: Disilaquinodimethane vs Triplet Bis(silyl radical). Journal of the American Chemical Society 2011, 133 (15) , 5773-5775. https://doi.org/10.1021/ja2014746
  11. Dennis Sheberla, Boris Tumanskii, Dmitry Bravo-Zhivotovskii, Gregory Molev, Victoria Molev, Vladimir Ya. Lee, Kazunori Takanashi, Akira Sekiguchi, and Yitzhak Apeloig . Electronic Structure of Bis(silyl)carbon-, Bis(silyl)silicon-, and Bis(silyl)germanium-Centered Radicals (R3Si)2XE• (E = C, Si, Ge; X = H, Re(CO)5, F): EPR and DFT Studies. Organometallics 2010, 29 (21) , 5596-5606. https://doi.org/10.1021/om100812b
  12. Gregory Molev, Boris Tumanskii, Dennis Sheberla, Mark Botoshansky, Dmitry Bravo-Zhivotovskii and Yitzhak Apeloig. Isolable Photoreactive Polysilyl Radicals. Journal of the American Chemical Society 2009, 131 (33) , 11698-11700. https://doi.org/10.1021/ja905097b
  13. Marco Becker, Christoph Förster, Christian Franzen, Johannes Hartrath, Enzio Kirsten, Jörn Knuth, Karl W. Klinkhammer, Ajay Sharma and Dariush Hinderberger . Persistent Radicals of Trivalent Tin and Lead. Inorganic Chemistry 2008, 47 (21) , 9965-9978. https://doi.org/10.1021/ic801198p
  14. Anna Chrostowska, Alain Dargelos, Alain Graciaa, Patrick Baylère, Vladimir Ya. Lee, Masaaki Nakamoto and Akira Sekiguchi. Electronic Structure of Stable Radicals of the Heavy Group 14 Elements: UV-Photoelectron Spectroscopy Characterization. Organometallics 2008, 27 (13) , 2915-2917. https://doi.org/10.1021/om7012925
  15. Shigeyoshi Inoue, Masaaki Ichinohe and Akira Sekiguchi. The Isolable Cation Radical of Disilene: Synthesis, Characterization, and a Reversible One-Electron Redox System. Journal of the American Chemical Society 2008, 130 (19) , 6078-6079. https://doi.org/10.1021/ja801761w
  16. Shigeyoshi Inoue, Masaaki Ichinohe and Akira Sekiguchi. Isolable Alkali-Metal-Substituted Silyl Radicals (tBu2MeSi)2SiM (M = Li, Na, K): Electronically and Sterically Accessible Planar Silyl Radicals. Organometallics 2008, 27 (7) , 1358-1360. https://doi.org/10.1021/om8000185
  17. Takeshi Matsumoto, Takahiro Sasamori, Kazunobu Sato, Takeji Takui and Norihiro Tokitoh. Reduction of a Kinetically Stabilized Silabenzene Leading to the Formation of the Corresponding Anion Radical Species. Organometallics 2008, 27 (3) , 305-308. https://doi.org/10.1021/om701060a
  18. Vladimir Ya. Lee and Akira Sekiguchi. Stable Silyl, Germyl, and Stannyl Cations, Radicals, and Anions: Heavy Versions of Carbocations, Carbon Radicals, and Carbanions. Accounts of Chemical Research 2007, 40 (6) , 410-419. https://doi.org/10.1021/ar6000473
  19. Rei Kinjo,, Masaaki Ichinohe, and, Akira Sekiguchi. An Isolable Disilyne Anion Radical and a New Route to the Disilenide Ion upon Reduction of a Disilyne. Journal of the American Chemical Society 2007, 129 (1) , 26-27. https://doi.org/10.1021/ja066762x
  20. Vladimir Ya. Lee,, Tomohide Fukawa,, Masaaki Nakamoto,, Akira Sekiguchi,, Boris L. Tumanskii,, Miriam Karni, and, Yitzhak Apeloig. (tBu2MeSi)2SnSn(SiMetBu2)2:  A Distannene with a >SnSn< Double Bond That Is Stable Both in the Solid State and in Solution. Journal of the American Chemical Society 2006, 128 (35) , 11643-11651. https://doi.org/10.1021/ja063322x
  21. Masaaki Nakamoto,, Tomoki Yamasaki, and, Akira Sekiguchi. Stable Mononuclear Radical Anions of Heavier Group 13 Elements:  [(tBu2MeSi)3E•-]·[K+(2.2.2-Cryptand)] (E = Al, Ga). Journal of the American Chemical Society 2005, 127 (19) , 6954-6955. https://doi.org/10.1021/ja051814o
  22. Dmitry Bravo-Zhivotovskii,, Ilya Ruderfer,, Michael Yuzefovich,, Monica Kosa,, Mark Botoshansky,, Boris Tumanskii, and, Yitzhak Apeloig. Mercury-Substituted Silyl Radical Intermediates in Formation and Fragmentation of Geminal Dimercury Silyl Compounds. Organometallics 2005, 24 (11) , 2698-2704. https://doi.org/10.1021/om050118u
  23. Yutaka Ishida and, Akira Sekiguchi, , Kaoru Kobayashi and, Shigeru Nagase. 1,6,7-Trigermabicyclo[4.1.0]hept-3-en-7-yl:  The Isolable Bicyclic Germyl Radical. Organometallics 2004, 23 (21) , 4891-4896. https://doi.org/10.1021/om0400797
  24. Akira Sekiguchi,, Shigeyoshi Inoue,, Masaaki Ichinohe, and, Yoriko Arai. Isolable Anion Radical of Blue Disilene (tBu2MeSi)2SiSi(SiMetBu2)2 Formed upon One-Electron Reduction:  Synthesis and Characterization. Journal of the American Chemical Society 2004, 126 (31) , 9626-9629. https://doi.org/10.1021/ja040079y
  25. Tomohide Fukawa,, Masaaki Nakamoto,, Vladimir Ya. Lee, and, Akira Sekiguchi. Structural Diversity of the Tris(di-tert-butylmethylsilyl)stannyl Anion:  Monomeric vs Dimeric, Lithium Coordinated vs Lithium Free. Organometallics 2004, 23 (10) , 2376-2381. https://doi.org/10.1021/om0400090
  26. Philip P. Power. Persistent and Stable Radicals of the Heavier Main Group Elements and Related Species. Chemical Reviews 2003, 103 (3) , 789-810. https://doi.org/10.1021/cr020406p
  27. Masaaki Nakamoto,, Tomohide Fukawa,, Vladimir Ya. Lee, and, Akira Sekiguchi. Nearly Planar Nonsolvated Monomeric Silyl- and Germyllithiums as a Result of an Intramolecular CH−Li Agostic Interaction. Journal of the American Chemical Society 2002, 124 (51) , 15160-15161. https://doi.org/10.1021/ja021142r
  28. Shintaro Takahashi, Kazuki Nakaya, María Frutos, Antoine Baceiredo, Nathalie Saffon‐Merceron, Stéphane Massou, Norio Nakata, Daisuke Hashizume, Vicenç Branchadell, Tsuyoshi Kato. Synthesis of a Stable N‐Hetero ‐ Rh I ‐Metallacyclic Silanone. Angewandte Chemie 2020, 132 (37) , 16071-16075. https://doi.org/10.1002/ange.202006088
  29. Shintaro Takahashi, Kazuki Nakaya, María Frutos, Antoine Baceiredo, Nathalie Saffon‐Merceron, Stéphane Massou, Norio Nakata, Daisuke Hashizume, Vicenç Branchadell, Tsuyoshi Kato. Synthesis of a Stable N‐Hetero ‐ Rh I ‐Metallacyclic Silanone. Angewandte Chemie International Edition 2020, 59 (37) , 15937-15941. https://doi.org/10.1002/anie.202006088
  30. Zhongtao Feng, Yong Fang, Huapeng Ruan, Yue Zhao, Gengwen Tan, Xinping Wang. Stable Radical Cation and Dication of an N‐Heterocyclic Carbene Stabilized Digallene: Synthesis, Characterization and Reactivity. Angewandte Chemie 2020, 132 (17) , 6835-6840. https://doi.org/10.1002/ange.202000051
  31. Zhongtao Feng, Yong Fang, Huapeng Ruan, Yue Zhao, Gengwen Tan, Xinping Wang. Stable Radical Cation and Dication of an N‐Heterocyclic Carbene Stabilized Digallene: Synthesis, Characterization and Reactivity. Angewandte Chemie International Edition 2020, 59 (17) , 6769-6774. https://doi.org/10.1002/anie.202000051
  32. Haiyan Cui, Dengmengfei Xiao, Li Zhang, Huapeng Ruan, Yong Fang, Yue Zhao, Gengwen Tan, Lili Zhao, Gernot Frenking, Matthias Driess, Xinping Wang. Isolable cyclic radical cations of heavy main-group elements. Chemical Communications 2020, 56 (14) , 2167-2170. https://doi.org/10.1039/C9CC09582A
  33. Richard Holzner, Dominik Reiter, Philipp Frisch, Shigeyoshi Inoue. DMAP-stabilized bis(silyl)silylenes as versatile synthons for organosilicon compounds. RSC Advances 2020, 10 (6) , 3402-3406. https://doi.org/10.1039/C9RA10628F
  34. J. Robin Fulton. Germanium, Tin and Lead. 2020,,https://doi.org/10.1016/B978-0-12-409547-2.14900-5
  35. . Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. 2020,,https://doi.org/
  36. Philipp Frisch, Shigeyoshi Inoue. NHC-stabilized silyl-substituted silyliumylidene ions. Dalton Transactions 2019, 48 (28) , 10403-10406. https://doi.org/10.1039/C9DT02010A
  37. Richard Holzner, Alexander Kaushansky, Boris Tumanskii, Philipp Frisch, Fabian Linsenmann, Shigeyoshi Inoue. Isolation of a Relatively Air-Stable, Bulky Silyl-Substituted, Neutral Silicon-Centered Radical. European Journal of Inorganic Chemistry 2019, 2019 (25) , 2977-2981. https://doi.org/10.1002/ejic.201900522
  38. Daniel Pinchuk, Yosi Kratish, Jomon Mathew, Lieby Zborovsky, Dmitry Bravo‐Zhivotovskii, Boris Tumanskii, Yitzhak Apeloig. Generation and EPR Spectroscopy of the First Silenyl Radicals, R 2 C=Si . −R: Experiment and Theory. Angewandte Chemie 2019, 131 (22) , 7513-7517. https://doi.org/10.1002/ange.201901772
  39. Daniel Pinchuk, Yosi Kratish, Jomon Mathew, Lieby Zborovsky, Dmitry Bravo‐Zhivotovskii, Boris Tumanskii, Yitzhak Apeloig. Generation and EPR Spectroscopy of the First Silenyl Radicals, R 2 C=Si . −R: Experiment and Theory. Angewandte Chemie International Edition 2019, 58 (22) , 7435-7439. https://doi.org/10.1002/anie.201901772
  40. Boris L. Tumanskii, Denis S. Sabirov, Stanislav P. Solodovnikov, Yury I. Lyakhovetsky. Manganese( iii ) acetate-mediated activation of C–H bonds of weak CH-acids; addition of o -carborane, its derivatives, and some other CH-acids to [60]-fullerene. Dalton Transactions 2019, 48 (6) , 2046-2058. https://doi.org/10.1039/C8DT04565H
  41. Priyabrata Ghana. Open-Shell Heavier Tetrylidyne Complexes of Group 6 Transition Metals. 2019,,, 77-81. https://doi.org/10.1007/978-3-030-02625-7_3
  42. Priyabrata Ghana. Synthesis, Characterization and Reactivity of Ylidyne and μ-Ylido Complexes Supported by Scorpionato Ligands. 2019,,https://doi.org/10.1007/978-3-030-02625-7
  43. Jie-Sheng Li, Jie Wu. Recent Developments in the Photo-Mediated Generation of Silyl Radicals and Their Application in Organic Synthesis. ChemPhotoChem 2018, 2 (10) , 839-846. https://doi.org/10.1002/cptc.201800110
  44. Ryan R. Maar, Sara D. Catingan, Viktor N. Staroverov, Joe B. Gilroy. Formazanate Complexes of Hypervalent Group 14 Elements as Precursors to Electronically Stabilized Radicals. Angewandte Chemie 2018, 130 (31) , 10018-10022. https://doi.org/10.1002/ange.201806097
  45. Ryan R. Maar, Sara D. Catingan, Viktor N. Staroverov, Joe B. Gilroy. Formazanate Complexes of Hypervalent Group 14 Elements as Precursors to Electronically Stabilized Radicals. Angewandte Chemie International Edition 2018, 57 (31) , 9870-9874. https://doi.org/10.1002/anie.201806097
  46. Vladimir Ya. Lee, Akira Sekiguchi. Silicon-Centered Cations. 2017,,, 197-230. https://doi.org/10.1016/B978-0-12-801981-8.00005-8
  47. . Organosilicon Compounds. 2017,,https://doi.org/
  48. Boris Tumanskii, Miriam Karni, Yitzhak Apeloig. Silicon-Centered Radicals. 2017,,, 231-294. https://doi.org/10.1016/B978-0-12-801981-8.00006-X
  49. . Organosilicon Compounds. 2017,,https://doi.org/
  50. Anna Chrostowska, Clovis Darrigan. UV-Photoelectron Spectroscopy of Organosilicon Compounds. 2017,,, 115-166. https://doi.org/10.1016/B978-0-12-814213-4.00004-6
  51. . Organosilicon Compounds. 2017,,https://doi.org/
  52. Lirong Yu, Yanglizhi Li, Xi Wang, Xingyong Wang, Panpan Zhou, Shangda Jiang, Xiaobo Pan. Consecutive reduction, radical-cyclization, and oxidative-dehydrogenation reaction of ortho-substituted diboryl compounds. Chemical Communications 2017, 53 (70) , 9737-9740. https://doi.org/10.1039/C7CC05689C
  53. Daniel Pinchuk, Jomon Mathew, Alexander Kaushansky, Dmitry Bravo-Zhivotovskii, Yitzhak Apeloig. Isolation and Characterization, Including by X-ray Crystallography, of Contact and Solvent-Separated Ion Pairs of Silenyl Lithium Species. Angewandte Chemie 2016, 128 (35) , 10414-10418. https://doi.org/10.1002/ange.201603640
  54. Daniel Pinchuk, Jomon Mathew, Alexander Kaushansky, Dmitry Bravo-Zhivotovskii, Yitzhak Apeloig. Isolation and Characterization, Including by X-ray Crystallography, of Contact and Solvent-Separated Ion Pairs of Silenyl Lithium Species. Angewandte Chemie International Edition 2016, 55 (35) , 10258-10262. https://doi.org/10.1002/anie.201603640
  55. Kartik Chandra Mondal, Sudipta Roy, Herbert W. Roesky. Silicon based radicals, radical ions, diradicals and diradicaloids. Chemical Society Reviews 2016, 45 (4) , 1080-1111. https://doi.org/10.1039/C5CS00739A
  56. Vladimir Ya. Lee, Akira Sekiguchi. Heavier Group 14 Element Redox Systems. 2015,,, 545-561. https://doi.org/10.1002/9781118858981.ch19
  57. . Organic Redox Systems. 2016,,https://doi.org/10.1002/9781118858981
  58. Shinsuke Nishida, Yasushi Morita. Air-Stable Redox-Active Neutral Radicals. 2015,,, 177-243. https://doi.org/10.1002/9781118858981.ch6
  59. . Organic Redox Systems. 2016,,https://doi.org/10.1002/9781118858981
  60. Charles S. Weinert. Germanium: Organometallic Chemistry. 2015,,, 1-18. https://doi.org/10.1002/9781119951438.eibc0075.pub3
  61. . Encyclopedia of Inorganic and Bioinorganic Chemistry. 2011,,https://doi.org/
  62. Marius I. Arz, Martin Straßmann, Andreas Meyer, Gregor Schnakenburg, Olav Schiemann, Alexander C. Filippou. One-Electron Oxidation of a Disilicon(0) Compound: An Experimental and Theoretical Study of [Si 2 ] + Trapped by N-Heterocyclic Carbenes. Chemistry - A European Journal 2015, 21 (35) , 12509-12516. https://doi.org/10.1002/chem.201502199
  63. Takeshi Nozawa, Masaaki Ichinohe, Akira Sekiguchi. 1,3,5-[( t Bu 2 MeSi) 2 Si] 3 C 6 H 3 : Isolable Si-centered Triradical with a High-spin Quartet Ground State. Chemistry Letters 2015, 44 (1) , 56-57. https://doi.org/10.1246/cl.140913
  64. Alexandra Budanow, Haleh Hashemi Haeri, Inge Sänger, Frauke Schödel, Michael Bolte, Thomas Prisner, Matthias Wagner, Hans-Wolfram Lerner. Disupersilylperoxo Radical Anion [ t Bu 3 SiOOSi t Bu 3 ] ⋅− : An Intermediate of Supersilanide Oxidation. Chemistry - A European Journal 2014, 20 (33) , 10236-10239. https://doi.org/10.1002/chem.201403854
  65. Siew-Peng Chia, Emma Carter, Hong-Wei Xi, Yongxin Li, Cheuk-Wai So. Group II Metal Complexes of the Germylidendiide Dianion Radical and Germylidenide Anion. Angewandte Chemie 2014, 126 (32) , 8595-8598. https://doi.org/10.1002/ange.201404357
  66. Siew-Peng Chia, Emma Carter, Hong-Wei Xi, Yongxin Li, Cheuk-Wai So. Group II Metal Complexes of the Germylidendiide Dianion Radical and Germylidenide Anion. Angewandte Chemie International Edition 2014, 53 (32) , 8455-8458. https://doi.org/10.1002/anie.201404357
  67. Kanako Taira, Masaaki Ichinohe, Akira Sekiguchi. Isolable Aryl-Substituted Silyl Radicals: Synthesis, Characterization, and Reactivity. Chemistry - A European Journal 2014, 20 (30) , 9342-9348. https://doi.org/10.1002/chem.201402482
  68. Johann Hlina, Judith Baumgartner, Christoph Marschner, Lena Albers, Thomas Müller, Viatcheslav V. Jouikov. Formation and Properties of a Bicyclic Silylated Digermene. Chemistry - A European Journal 2014, 20 (30) , 9357-9366. https://doi.org/10.1002/chem.201402785
  69. Robert West, Kerim Samedov, Amitabha Mitra, Paul W. Percival, Jean-Claude Brodovitch, Graeme Langille, Brett M. McCollum, Takeaki Iwamoto, Shintaro Ishida, Cameron Jones, Jiaye Li. Germanium-centered free radicals studied by muon spin spectroscopy. Canadian Journal of Chemistry 2014, 92 (6) , 508-513. https://doi.org/10.1139/cjc-2013-0427
  70. . Akira Sekiguchi. Angewandte Chemie 2014,,, 4842-4842. https://doi.org/10.1002/ange.201310966
  71. . Akira Sekiguchi. Angewandte Chemie International Edition 2014,,, 4746-4746. https://doi.org/10.1002/anie.201310966
  72. Hitoshi Maruyama, Hideyuki Nakano, Masaaki Nakamoto, Akira Sekiguchi. High-Power Electrochemical Energy Storage System Employing Stable Radical Pseudocapacitors. Angewandte Chemie 2014, 126 (5) , 1348-1352. https://doi.org/10.1002/ange.201308302
  73. Hitoshi Maruyama, Hideyuki Nakano, Masaaki Nakamoto, Akira Sekiguchi. High-Power Electrochemical Energy Storage System Employing Stable Radical Pseudocapacitors. Angewandte Chemie International Edition 2014, 53 (5) , 1324-1328. https://doi.org/10.1002/anie.201308302
  74. Soichiro Kyushin, Shintaro Ishida, Akihiro Tsurusaki, Kyohei Otsuka. Effect of Ring Sizes of Cyclooligosilanes on Construction of Organosilicon Clusters. Journal of Synthetic Organic Chemistry, Japan 2014, 72 (11) , 1290-1297. https://doi.org/10.5059/yukigoseikyokaishi.72.1290
  75. Kartik Chandra Mondal, Herbert W. Roesky, A. Claudia Stückl, Fabian Ehret, Wolfgang Kaim, Birger Dittrich, Bholanath Maity, Debasis Koley. Formation of Trichlorosilyl-Substituted Carbon-Centered Stable Radicals through the Use of π-Accepting Carbenes. Angewandte Chemie 2013, 125 (45) , 12020-12023. https://doi.org/10.1002/ange.201300668
  76. Kartik Chandra Mondal, Herbert W. Roesky, A. Claudia Stückl, Fabian Ehret, Wolfgang Kaim, Birger Dittrich, Bholanath Maity, Debasis Koley. Formation of Trichlorosilyl-Substituted Carbon-Centered Stable Radicals through the Use of π-Accepting Carbenes. Angewandte Chemie International Edition 2013, 52 (45) , 11804-11807. https://doi.org/10.1002/anie.201300668
  77. Takeaki Iwamoto, Shintaro Ishida. Multiple Bonds with Silicon: Recent Advances in Synthesis, Structure, and Functions of Stable Disilenes. 2013,,, 125-202. https://doi.org/10.1007/430_2013_119
  78. . Functional Molecular Silicon Compounds II. 2014,,https://doi.org/10.1007/978-3-319-03734-9
  79. T. Chivers, J. Konu. Stable and Persistent Radicals of Group 13-17 Elements. 2013,,, 349-373. https://doi.org/10.1016/B978-0-08-097774-4.00116-9
  80. . Comprehensive Inorganic Chemistry II. 2013,,https://doi.org/
  81. Caleb D. Martin, Michele Soleilhavoup, Guy Bertrand. Carbene-stabilized main group radicals and radical ions. Chemical Science 2013, 4 (8) , 3020. https://doi.org/10.1039/c3sc51174j
  82. Boris Tumanskii, Miriam Karni, Yitzhak Apeloig. Persistent and Stable Silyl Radicals. 2012,,https://doi.org/10.1002/9781119953678.rad066
  83. , . Encyclopedia of Radicals in Chemistry, Biology and Materials. 2012,,https://doi.org/
  84. Mark Banaszak Holl, David R. Peck. Germanium: Organometallic Chemistry. 2011,,https://doi.org/10.1002/9781119951438.eibc0075
  85. . Encyclopedia of Inorganic and Bioinorganic Chemistry. 2011,,https://doi.org/
  86. Hideki Sakurai. Silicon: Organosilicon Chemistry. 2011,,https://doi.org/10.1002/9781119951438.eibc0204
  87. . Encyclopedia of Inorganic and Bioinorganic Chemistry. 2011,,https://doi.org/
  88. Vladimir Ya. Lee, Yuki Ito, Akira Sekiguchi. 1,2-Dibromo- 3 Δ-1,2,3,4-disiladigermetene. Phosphorus, Sulfur, and Silicon and the Related Elements 2011, 186 (6) , 1351-1355. https://doi.org/10.1080/10426507.2010.543104
  89. . Heavy Analogs of Organic Free Radicals: Si-, Ge-, Sn- and Pb-Centered Radicals. 2010,,, 45-88. https://doi.org/10.1002/9780470669266.ch2
  90. Vladimir Ya. Lee, Akira Sekiguchi. Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb. 2010,,https://doi.org/
  91. . Heavy Analogs of Carbanions: Si-, Ge-, Sn- and Pb-Centered Anions. 2010,,, 89-138. https://doi.org/10.1002/9780470669266.ch3
  92. Vladimir Ya. Lee, Akira Sekiguchi. Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb. 2010,,https://doi.org/
  93. Jari Konu, Tristram Chivers. Stable Radicals of the Heavy p-Block Elements. 2010,,, 381-406. https://doi.org/10.1002/9780470666975.ch10
  94. . Stable Radicals. 2010,,https://doi.org/10.1002/9780470666975
  95. Norio Nakata, Sayaka Masubuchi, Akira Sekiguchi. Spiro[2,5-dibenzo-1,4-disilacyclohexa-2,5-diene-1,7′-2′,5′- dibenzo-1′,4′,7′-trisilanorbornadiene]: Unusual Dimerization of Silyl-Substituted 9,10-Disila(Dewar Anthracene). Phosphorus, Sulfur, and Silicon and the Related Elements 2010, 185 (5-6) , 957-963. https://doi.org/10.1080/10426501003771385
  96. Dennis Kurzbach, Shenglai Yao, Dariush Hinderberger, Karl W. Klinkhammer. EPR spectroscopic characterization of persistent germyl-substituted Pb(iii)- and Sn(iii)-radicals. Dalton Transactions 2010, 39 (28) , 6449. https://doi.org/10.1039/c001144d
  97. Sakya S. Sen, Herbert W. Roesky, Kathrin Meindl, Daniel Stern, Julian Henn, A. Claudia Stückl, Dietmar Stalke. Synthesis, structure, and theoretical investigation of amidinato supported 1,4-disilabenzene. Chemical Communications 2010, 46 (32) , 5873. https://doi.org/10.1039/c0cc01753a
  98. Haiying Bie, Arthur Mar. Ge Pairs and Sb Ribbons in Rare-Earth Germanium Antimonides RE 12 Ge7− x Sb 21 ( RE =La-Pr). Chemistry - An Asian Journal 2009, 4 (9) , 1465-1473. https://doi.org/10.1002/asia.200900063
  99. James Y. Becker, Vladimir Ya. Lee, Masaaki Nakamoto, Akira Sekiguchi, Anna Chrostowska, Alain Dargelos. Electrochemical Properties and Computations of Stable Radicals of the Heavy Group 14 Elements (Si, Ge, and Sn). Chemistry - A European Journal 2009, 15 (34) , 8480-8484. https://doi.org/10.1002/chem.200900935
  100. Akira Sekiguchi, Rei Kinjo, Masaaki Ichinohe. Interaction of π-bonds of the silicon–silicon triple bond with alkali metals: An isolable anion radical upon reduction of a disilyne. Synthetic Metals 2009, 159 (9-10) , 773-775. https://doi.org/10.1016/j.synthmet.2009.01.007

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

OOPS

You have to login with your ACS ID befor you can login with your Mendeley account.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE