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Collect. Czech. Chem. Commun. 1999, 64, 1001-1012
https://doi.org/10.1135/cccc19991001

Cation-π Interactions in the Solid State: Crystal Structures of M+(benzene)2CB11Me12- (M = Tl, Cs, Rb, K, Na) and Li+(toluene)CB11Me12-

Benjamin T. King, Bruce C. Noll and Josef Michl*

University of Colorado, Department of Chemistry and Biochemistry, Boulder, Colorado 80309-0215, U.S.A.

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  • Jie Xiaoming, Li Jun, Daniliuc Constantin G., Wübker Anna‐Lena, Hansen Michael Ryan, Eckert Hellmut, Mück‐Lichtenfeld Christian, Kehr Gerald, Erker Gerhard: The Bis(η 6 ‐benzene)lithium Cation: A Fundamental Main‐Group Organometallic Species. Angewandte Chemie 2021, 133, 23061. <https://doi.org/10.1002/ange.202108376>
  • Jie Xiaoming, Li Jun, Daniliuc Constantin G., Wübker Anna‐Lena, Hansen Michael Ryan, Eckert Hellmut, Mück‐Lichtenfeld Christian, Kehr Gerald, Erker Gerhard: The Bis(η 6 ‐benzene)lithium Cation: A Fundamental Main‐Group Organometallic Species. Angew Chem Int Ed 2021, 60, 22879. <https://doi.org/10.1002/anie.202108376>
  • Riddlestone Ian M., Kraft Anne, Schaefer Julia, Krossing Ingo: Die Schöne (WCA) und das (kationische) Biest: Neues aus der Chemie von und mit schwach koordinierenden Anionen. Angew. Chem. 2018, 130, 14178. <https://doi.org/10.1002/ange.201710782>
  • Riddlestone Ian M., Kraft Anne, Schaefer Julia, Krossing Ingo: Taming the Cationic Beast: Novel Developments in the Synthesis and Application of Weakly Coordinating Anions. Angew. Chem. Int. Ed. 2018, 57, 13982. <https://doi.org/10.1002/anie.201710782>
  • Merna Jan, Vlček Petr, Volkis Victoria, Michl Josef: Li+ Catalysis and Other New Methodologies for the Radical Polymerization of Less Activated Olefins. Chem. Rev. 2016, 116, 771. <https://doi.org/10.1021/acs.chemrev.5b00485>
  • Arz Marius I., Straßmann Martin, Geiß Daniel, Schnakenburg Gregor, Filippou Alexander C.: Addition of Small Electrophiles to N-Heterocyclic-Carbene-Stabilized Disilicon(0): A Revisit of the Isolobal Concept in Low-Valent Silicon Chemistry. J. Am. Chem. Soc. 2016, 138, 4589. <https://doi.org/10.1021/jacs.6b01018>
  • Sarmah Nabajit, Bhattacharyya Pradip Kr., Bania Kusum K.: Substituent and Solvent Effects on the Absorption Spectra of Cation−π Complexes of Benzene and Borazine: A Theoretical Study. J. Phys. Chem. A 2014, 118, 3760. <https://doi.org/10.1021/jp5021966>
  • Douvris Christos, Michl Josef: Update 1 of: Chemistry of the Carba-closo-dodecaborate(−) Anion, CB11H12–. Chem. Rev. 2013, 113, PR179. <https://doi.org/10.1021/cr400059k>
  • Pramanik Chandrani, Li Yushu, Singh Anup, Lin Weimin, Hodgson Jennifer L., Briggs Jonathan B., Ellis Simka, Müller Peter, McGruer Nicol E., Miller Glen P.: Water soluble pentacene. J. Mater. Chem. C 2013, 1, 2193. <https://doi.org/10.1039/c3tc00278k>
  • Wrede Michael, Ganza Viktoria, Kannenberg Geraldt, Rominger Frank, Straub Bernd F.: Synthesis, structure, and unprecedented solubility of lipophilic borate salts. Inorganica Chimica Acta 2011, 369, 71. <https://doi.org/10.1016/j.ica.2010.12.039>
  • Straub Bernd F., Wrede Michael, Schmid Karin, Rominger Frank: A Lipophilic, Fluorine‐Free, Thermostable, Inexpensive, S 4 ‐Symmetric, Highly Soluble, Weakly Coordinating, Protolabile Aluminate. Eur. J. Inorg. Chem. 2010, 2010, 1907. <https://doi.org/10.1002/ejic.201000197>
  • Krieck Sven, Görls Helmar, Westerhausen Matthias: Alkali Metal-Stabilized 1,3,5-Triphenylbenzene Monoanions: Synthesis and Characterization of the Lithium, Sodium, and Potassium Complexes. Organometallics 2010, 29, 6790. <https://doi.org/10.1021/om1009632>
  • Shukla Ruchi, Lindeman Sergey V., Rathore Rajendra: Terphenyl crowns: a new family of receptors containing ethereal canopies that direct potassium cation onto benzenoid platforms for cation–π interactions. Chem. Commun. 2009, 5600. <https://doi.org/10.1039/b912796h>
  • Kim Dongwook, Lee Eun Cheol, Kim Kwang S., Tarakeshwar P.: Cation−π−Anion Interaction:  A Theoretical Investigation of the Role of Induction Energies. J. Phys. Chem. A 2007, 111, 7980. <https://doi.org/10.1021/jp073337x>
  • Vyakaranam Kamesh, Janoušek Zbyněk, Eriksson Ludvig, Michl Josef: Preparation of undecamethylated and hexamethylated 1-halocarba-closo-dodecaborate anions. Heteroatom Chem. 2006, 17, 217. <https://doi.org/10.1002/hc.20224>
  • Körbe Stefanie, Schreiber Peter J., Michl Josef: Chemistry of the Carba-closo-dodecaborate(−) Anion, CB11H12-. Chem. Rev. 2006, 106, 5208. <https://doi.org/10.1021/cr050548u>
  • Zharov Ilya, Havlas Zdenek, Orendt Anita M., Barich Dewey H., Grant David M., Fete Matthew G., Michl Josef: CB11Me11 Boronium Ylides:  Carba-closo-dodecaboranes with a Naked Boron Vertex. J. Am. Chem. Soc. 2006, 128, 6089. <https://doi.org/10.1021/ja054256m>
  • Vyakaranam Kamesh, Körbe Stefanie, Michl Josef: Air-Initiated Radical Polymerization of Lithium Salts of ω-(Undecamethylcarba-closo-dodecaboran-1‘-yl)alk-1-enes, CH2CH(CH2)n-2C(BMe)11- Li+. J. Am. Chem. Soc. 2006, 128, 5680. <https://doi.org/10.1021/ja054967k>
  • Shukla Ruchi, Lindeman Sergey V., Rathore Rajendra: A Polyaromatic Receptor with an Ethereal Fence that Directs K+ for Effective Cation−π Interaction. J. Am. Chem. Soc. 2006, 128, 5328. <https://doi.org/10.1021/ja060502y>
  • Cametti Massimo, Nissinen Maija, Dalla Cort Antonella, Mandolini Luigi, Rissanen Kari: Recognition of Alkali Metal Halide Contact Ion Pairs by Uranyl−Salophen Receptors Bearing Aromatic Sidearms. The Role of Cation−π Interactions. J. Am. Chem. Soc. 2005, 127, 3831. <https://doi.org/10.1021/ja042807n>
  • Clarke Adam J., Ingleson Michael J., Kociok-Köhn Gabriele, Mahon Mary F., Patmore Nathan J., Rourke Jonathan P., Ruggiero Giuseppe D., Weller Andrew S.: Silver−Phosphine Complexes of the Highly Methylated Carborane Monoanion [closo-1-H-CB11Me11]-. J. Am. Chem. Soc. 2004, 126, 1503. <https://doi.org/10.1021/ja038173m>
  • Janoušek Zbyněk, Lehmann Uwe, Častulík Jakub, Císařová Ivana, Michl Josef: Li+-Induced σ-Bond Metathesis:  Aryl for Methyl Exchange on Boron in a Methylated Monocarbadodecaborate Anion. J. Am. Chem. Soc. 2004, 126, 4060. <https://doi.org/10.1021/ja0387857>
  • Zharov Ilya, Weng Tsu-Chien, Orendt Anita M., Barich Dewey H., Penner-Hahn James, Grant David M., Havlas Zdenek, Michl Josef: Metal Cation−Methyl Interactions in CB11Me12- Salts of Me3Ge+, Me3Sn+, and Me3Pb+. J. Am. Chem. Soc. 2004, 126, 12033. <https://doi.org/10.1021/ja0475205>
  • Hu Jiaxin, Barbour Leonard J., Gokel George W.: Ferrocene derivatives as receptors to explore ammonium cation–π interactions. New J. Chem. 2004, 28, 907. <https://doi.org/10.1039/B313422A>
  • Hu Jiaxin, Barbour Leonard J., Gokel George W.: Cation-π Interactions Between Alkali Metal Cations and Neutral Double Bonds. Collect. Czech. Chem. Commun. 2004, 69, 1050. <https://doi.org/10.1135/cccc20041050>
  • Fukin Georgy K., Lindeman Sergey V., Kochi Jay K.: Molecular Structures of Cation···π(Arene) Interactions for Alkali Metals with π- and σ-Modalities. J. Am. Chem. Soc. 2002, 124, 8329. <https://doi.org/10.1021/ja0203465>
  • Forbes Glenn C., Kennedy Alan R., Mulvey Robert E., Roberts Brett A., Rowlings René B.: Alkali Metal Cation−π Interactions Stabilized Solely by [M{N(SiMe3)2}3]- Anions (M = Mg or Zn):  The Competing Influence of Alkali Metal···C(Me) Agostic Interactions. Organometallics 2002, 21, 5115. <https://doi.org/10.1021/om020596u>
  • Hu Jiaxin, Barbour Leonard J., Gokel George W.: Probing alkali metal–π interactions with the side chain residue of tryptophan. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5121. <https://doi.org/10.1073/pnas.082645599>
  • Krossing Ingo: The Facile Preparation of Weakly Coordinating Anions: Structure and Characterisation of Silverpolyfluoroalkoxyaluminates AgAl(ORF)4, Calculation of the Alkoxide Ion Affinity. Chem Eur J 2001, 7, 490. <https://doi.org/10.1002/1521-3765(20010119)7:2<490::AID-CHEM490>3.0.CO;2-I>
  • Krossing Ingo: The Facile Preparation of Weakly Coordinating Anions: Structure and Characterisation of Silverpolyfluoroalkoxyaluminates AgAl(ORF)4, Calculation of the Alkoxide Ion Affinity. Chem. Eur. J. 2001, 7, 490. <https://doi.org/10.1002/1521-3765(20010119)7:2<490::AID-CHEM490>3.0.CO;2-I>
  • Gokel George W., Barbour Leonard J., De Wall Stephen L., Meadows Eric S.: Macrocyclic polyethers as probes to assess and understand alkali metal cation-π interactions. Coordination Chemistry Reviews 2001, 222, 127. <https://doi.org/10.1016/S0010-8545(01)00380-0>
  • Meadows Eric S., Barbour Leonard J., Ferdani Riccardo, Gokel George W.: Dimer formation in alkali metal complexes of 15- and 18-Membered indole-containing lariat ether amides. Journal of Supramolecular Chemistry 2001, 1, 111. <https://doi.org/10.1016/S1472-7862(01)00016-8>
  • Ferdani Riccardo, Barbour Leonard J, Hu Jiaxin, Djedovič Natasha K, Gokel George W: Solid state structures of N-2-(3-indolylethyl)aza-9-crown-3, N,N′-bis(2-(3-indolylethyl))-4,13-diaza-18-crown-6, and their protonated forms. Journal of Supramolecular Chemistry 2001, 1, 305. <https://doi.org/10.1016/S1472-7862(02)00058-8>
  • Hu Zhengbo, Gorun Sergiu M.: Synthesis and Characterization of Fluorinated Tris(pyrazolyl)borate Complexes. Observation of an (η5-Pyrazole)−K+ Interaction in the Solid State. Inorg. Chem. 2001, 40, 667. <https://doi.org/10.1021/ic000860g>
  • Moss Stefan, King Benjamin T., de Meijere Armin, Kozhushkov Sergei I., Eaton Philip E., Michl Josef: LiCB11Me12:  A Catalyst for Pericyclic Rearrangements. Org. Lett. 2001, 3, 2375. <https://doi.org/10.1021/ol0161864>
  • Franken Andreas, King Benjamin T., Rudolph Jens, Rao Photon, Noll Bruce C., Michl Josef: Preparation of [closo-CB11H12]- by Dichlorocarbene Insertion Into [nido-B11H14]-. Collect. Czech. Chem. Commun. 2001, 66, 1238. <https://doi.org/10.1135/cccc20011238>
  • Gokel George W., De Wall Stephen L., Meadows Eric S.: Experimental Evidence for Alkali Metal Cation−π Interactions. Eur. J. Org. Chem. 2000, 2000, 2967. <https://doi.org/10.1002/1099-0690(200009)2000:17<2967::AID-EJOC2967>3.0.CO;2-O>
  • Burns Carol J., Clark David L., Donohoe Robert J., Duval Paul B., Scott Brian L., Tait C. Drew: A Trigonal Bipyramidal Uranyl Amido Complex:  Synthesis and Structural Characterization of [Na(THF)2][UO2(N(SiMe3)2)3]. Inorg. Chem. 2000, 39, 5464. <https://doi.org/10.1021/ic0003168>
  • King Benjamin T., Michl Josef: The Explosive “Inert” Anion CB11(CF3)12-. J. Am. Chem. Soc. 2000, 122, 10255. <https://doi.org/10.1021/ja001573e>
  • De Wall Stephen L., Meadows Eric S., Barbour Leonard J., Gokel George W.: Synthetic receptors as models for alkali metal cation-π binding sites in proteins. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 6271. <https://doi.org/10.1073/pnas.97.12.6271>