Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium
Waerder B, Steinhauer S, Neumann B, Stammler H-G, Mix A, Vishnevskiy Y, Hoge B, Mitzel NW (2014)
Angewandte Chemie International Edition 53(43): 11640-11644.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Abstract / Bemerkung
Lithium carbenoids are versatile compounds for synthesis owing to their intriguing ambiphilic behavior. Although this class of compounds has been known for several years, few solid-state structures exist because of their high reactivity and often low thermal stability. Using cryo X-ray techniques, we were now able to elucidate the first solid-state structure of a Li/F alkyl carbenoid, pentafluoroethyllithium (LiC2F5), finally yielding a prototype for investigating structurereactivity relationships for this class of molecules. The compound forms a diethyl ether-solvated dimer bridged by a rare C-F-Li link. Complementary NMR spectroscopy studies in solution show dynamic processes and indicate rapid exchange of starting material and product. Theoretical investigations help to understand the formation of the observed unusual structural motif.
Stichworte
lithium;
aggregation;
carbenoid;
fluorine;
crystal structure
Erscheinungsjahr
2014
Zeitschriftentitel
Angewandte Chemie International Edition
Band
53
Ausgabe
43
Seite(n)
11640-11644
ISSN
1433-7851
Page URI
https://pub.uni-bielefeld.de/record/2707743
Zitieren
Waerder B, Steinhauer S, Neumann B, et al. Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition. 2014;53(43):11640-11644.
Waerder, B., Steinhauer, S., Neumann, B., Stammler, H. - G., Mix, A., Vishnevskiy, Y., Hoge, B., et al. (2014). Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition, 53(43), 11640-11644. doi:10.1002/anie.201406564
Waerder, Benedikt, Steinhauer, Simon, Neumann, Beate, Stammler, Hans-Georg, Mix, Andreas, Vishnevskiy, Yury, Hoge, Berthold, and Mitzel, Norbert W. 2014. “Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium”. Angewandte Chemie International Edition 53 (43): 11640-11644.
Waerder, B., Steinhauer, S., Neumann, B., Stammler, H. - G., Mix, A., Vishnevskiy, Y., Hoge, B., and Mitzel, N. W. (2014). Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition 53, 11640-11644.
Waerder, B., et al., 2014. Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition, 53(43), p 11640-11644.
B. Waerder, et al., “Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium”, Angewandte Chemie International Edition, vol. 53, 2014, pp. 11640-11644.
Waerder, B., Steinhauer, S., Neumann, B., Stammler, H.-G., Mix, A., Vishnevskiy, Y., Hoge, B., Mitzel, N.W.: Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium. Angewandte Chemie International Edition. 53, 11640-11644 (2014).
Waerder, Benedikt, Steinhauer, Simon, Neumann, Beate, Stammler, Hans-Georg, Mix, Andreas, Vishnevskiy, Yury, Hoge, Berthold, and Mitzel, Norbert W. “Solid-State Structure of a Li/F Carbenoid: Pentafluoroethyllithium”. Angewandte Chemie International Edition 53.43 (2014): 11640-11644.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
18 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Ylide-Functionalization via Metalated Ylides: Synthesis and Structural Properties.
Schwarz C, Scherpf T, Rodstein I, Weismann J, Feichtner KS, Gessner VH., ChemistryOpen 8(5), 2019
PMID: 31123665
Schwarz C, Scherpf T, Rodstein I, Weismann J, Feichtner KS, Gessner VH., ChemistryOpen 8(5), 2019
PMID: 31123665
On Pentakis(pentafluoroethyl)stannate, [Sn(C2 F5 )5 ]- , and the Gas-Free Generation of Pentafluoroethyllithium, LiC2 F5.
Wiesemann M, Klösener J, Neumann B, Stammler HG, Hoge B., Chemistry 24(8), 2018
PMID: 29068093
Wiesemann M, Klösener J, Neumann B, Stammler HG, Hoge B., Chemistry 24(8), 2018
PMID: 29068093
Tris(pentafluoroethyl)stannane: Tin Hydride Chemistry with an Electron-Deficient Stannane.
Wiesemann M, Niemann M, Klösener J, Neumann B, Stammler HG, Hoge B., Chemistry 24(11), 2018
PMID: 29211312
Wiesemann M, Niemann M, Klösener J, Neumann B, Stammler HG, Hoge B., Chemistry 24(11), 2018
PMID: 29211312
The Dynamic Equilibrium of Hexakis(pentafluoroethyl)distannane Adducts [XSn(C2 F5 )3 {Sn(C2 F5 )3 }]- (X=Cl, Br, I, Sn(C2 F5 )3 ).
Wiesemann M, Klösener J, Neumann B, Stammler HG, Hoge B., Chemistry 24(17), 2018
PMID: 29240270
Wiesemann M, Klösener J, Neumann B, Stammler HG, Hoge B., Chemistry 24(17), 2018
PMID: 29240270
Synthesis and Reactivity of Donor-Stabilized Bis(pentafluoroethyl)stannylene [Sn(C2 F5 )2 (D)n ] (D=THF, DMAP, PMe3 , [Sn(C2 F5 )3 ]- ).
Klösener J, Wiesemann M, Niemann M, Neumann B, Stammler HG, Hoge B., Chemistry 24(17), 2018
PMID: 29315901
Klösener J, Wiesemann M, Niemann M, Neumann B, Stammler HG, Hoge B., Chemistry 24(17), 2018
PMID: 29315901
Pentafluoroethylated Compounds of Silicon, Germanium and Tin.
Wiesemann M, Hoge B., Chemistry 24(62), 2018
PMID: 29722451
Wiesemann M, Hoge B., Chemistry 24(62), 2018
PMID: 29722451
Taming Metal/Fluorine Carbenoids.
Molitor S, Feichtner KS, Gessner VH., Chemistry 23(11), 2017
PMID: 27906492
Molitor S, Feichtner KS, Gessner VH., Chemistry 23(11), 2017
PMID: 27906492
Gold(I) Fluorohalides: Theory and Experiment.
Baya M, Pérez-Bitrián A, Martínez-Salvador S, Casas JM, Menjón B, Orduna J., Chemistry 23(7), 2017
PMID: 27933670
Baya M, Pérez-Bitrián A, Martínez-Salvador S, Casas JM, Menjón B, Orduna J., Chemistry 23(7), 2017
PMID: 27933670
Pentafluoroethyl Bismuth Compounds.
Solyntjes S, Bader J, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 23(7), 2017
PMID: 27862439
Solyntjes S, Bader J, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 23(7), 2017
PMID: 27862439
Alkali Metal Chlorine and Bromine Carbenoids: Their Thermal Stability and Structural Properties.
Molitor S, Gessner VH., Chemistry 23(50), 2017
PMID: 28597985
Molitor S, Gessner VH., Chemistry 23(50), 2017
PMID: 28597985
The Tris(pentafluoroethyl)stannate(II) Anion, [Sn(C2 F5 )3 ]- -Synthesis and Reactivity.
Wiesemann M, Klösener J, Niemann M, Neumann B, Stammler HG, Hoge B., Chemistry 23(58), 2017
PMID: 28671288
Wiesemann M, Klösener J, Niemann M, Neumann B, Stammler HG, Hoge B., Chemistry 23(58), 2017
PMID: 28671288
Alkali Metal Carbenoids: A Case of Higher Stability of the Heavier Congeners.
Molitor S, Gessner VH., Angew Chem Int Ed Engl 55(27), 2016
PMID: 27100278
Molitor S, Gessner VH., Angew Chem Int Ed Engl 55(27), 2016
PMID: 27100278
Lithium Halomethylcarbenoids: Preparation and Use in the Homologation of Carbon Electrophiles.
Pace V, Holzer W, De Kimpe N., Chem Rec 16(4), 2016
PMID: 27381551
Pace V, Holzer W, De Kimpe N., Chem Rec 16(4), 2016
PMID: 27381551
Stability and reactivity control of carbenoids: recent advances and perspectives.
Gessner VH., Chem Commun (Camb) 52(81), 2016
PMID: 27498609
Gessner VH., Chem Commun (Camb) 52(81), 2016
PMID: 27498609
Synthesis of Functional Bis(pentafluoroethyl)silanes (C2 F5 )2 SiX2 , with X=H, F, Cl, Br, OPh, and O2 CCF3.
Schwarze N, Kurscheid B, Steinhauer S, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 22(48), 2016
PMID: 27778393
Schwarze N, Kurscheid B, Steinhauer S, Neumann B, Stammler HG, Ignat'ev N, Hoge B., Chemistry 22(48), 2016
PMID: 27778393
Nucleophilic Transfer Reactions of the [Si(C2 F5 )3 ]- Moiety.
Schwarze N, Steinhauer S, Neumann B, Stammler HG, Hoge B., Angew Chem Int Ed Engl 55(52), 2016
PMID: 27902862
Schwarze N, Steinhauer S, Neumann B, Stammler HG, Hoge B., Angew Chem Int Ed Engl 55(52), 2016
PMID: 27902862
The Tris(pentafluoroethyl)silanide Anion.
Schwarze N, Steinhauer S, Neumann B, Stammler HG, Hoge B., Angew Chem Int Ed Engl 55(52), 2016
PMID: 27902868
Schwarze N, Steinhauer S, Neumann B, Stammler HG, Hoge B., Angew Chem Int Ed Engl 55(52), 2016
PMID: 27902868
A Neutral Silicon/Phosphorus Frustrated Lewis Pair.
Waerder B, Pieper M, Körte LA, Kinder TA, Mix A, Neumann B, Stammler HG, Mitzel NW., Angew Chem Int Ed Engl 54(45), 2015
PMID: 26423202
Waerder B, Pieper M, Körte LA, Kinder TA, Mix A, Neumann B, Stammler HG, Mitzel NW., Angew Chem Int Ed Engl 54(45), 2015
PMID: 26423202
101 References
Daten bereitgestellt von Europe PubMed Central.
AUTHOR UNKNOWN, 0
Friedman, J. Am. Chem. Soc. 81(), 1959
Closs, J. Am. Chem. Soc. 86(), 1964
Anatomy of long-lasting love affairs with lithium carbenoids: past and present status and future prospects.
Capriati V, Florio S., Chemistry 16(14), 2010
PMID: 20222089
Capriati V, Florio S., Chemistry 16(14), 2010
PMID: 20222089
Simmons, J. Am. Chem. Soc. 81(), 1959
AUTHOR UNKNOWN, 0
Siegel, Top. Curr. Chem. 106(), 1982
Boche, 1995
The electrophilic nature of carbenoids, nitrenoids, and oxenoids.
Boche G, Lohrenz JC., Chem. Rev. 101(3), 2001
PMID: 11712501
Boche G, Lohrenz JC., Chem. Rev. 101(3), 2001
PMID: 11712501
α-Heteroatom-Substituted 1-Alkenyllithium Reagents: Carbanions and Carbenoids for C-C Bond Formation.
Braun M., Angew. Chem. Int. Ed. Engl. 37(4), 1998
PMID: 29711151
Braun M., Angew. Chem. Int. Ed. Engl. 37(4), 1998
PMID: 29711151
AUTHOR UNKNOWN, Angew. Chem. 110(), 1998
Braun, 2004
Florio, Curr. Org. Chem. 8(), 2004
AUTHOR UNKNOWN, 2014
AUTHOR UNKNOWN, 2010
AUTHOR UNKNOWN, 0
Addition of lithium carbenoids to isocyanates: a direct access to synthetically useful N-substituted 2-haloacetamides.
Pace V, Castoldi L, Holzer W., Chem. Commun. (Camb.) 49(75), 2013
PMID: 23938607
Pace V, Castoldi L, Holzer W., Chem. Commun. (Camb.) 49(75), 2013
PMID: 23938607
Facile B-H bond activation of borane by stable carbenoid species.
Heuclin H, Ho SY, Le Goff XF, So CW, Mezailles N., J. Am. Chem. Soc. 135(24), 2013
PMID: 23742108
Heuclin H, Ho SY, Le Goff XF, So CW, Mezailles N., J. Am. Chem. Soc. 135(24), 2013
PMID: 23742108
Reactivity of Stabilized Li/Cl Carbenoids towards Lewis Base Adducts of BH3: B-H Bond Activation versus Carbene Dimerization.
Molitor S, Gessner VH., Chemistry 19(36), 2013
PMID: 23897779
Molitor S, Gessner VH., Chemistry 19(36), 2013
PMID: 23897779
Niecke, Angew. Chem. Int. Ed. Engl. 34(), 1995
AUTHOR UNKNOWN, Angew. Chem. 107(), 1995
AUTHOR UNKNOWN, 0
Formation of a stable dicarbenoid and an unsaturated C2P2S2 ring from two-electron oxidation of the [C(PPh2S)2]2- dianion.
Konu J, Chivers T., Chem. Commun. (Camb.) (40), 2008
PMID: 18931764
Konu J, Chivers T., Chem. Commun. (Camb.) (40), 2008
PMID: 18931764
Boche, Chem. Ber. 125(), 1992
On the structure and ambiphilicity of a sulfonyl substituted α-chloro lithium base.
Becker J, Gessner VH., Dalton Trans 43(11), 2014
PMID: 24162557
Becker J, Gessner VH., Dalton Trans 43(11), 2014
PMID: 24162557
AUTHOR UNKNOWN, 0
Gassman, Tetrahedron Lett. 26(), 1985
Ernst, Inorg. Chem. 28(), 1989
Shevchenko, J. Fluorine Chem. 129(), 2008
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Kolomeitsev, Tetrahedron Lett. 44(), 2003
AUTHOR UNKNOWN, 0
Synthesis of five- and six-coordinate tris(pentafluoroethyl)fluorosilicates.
Steinhauer S, Stammler HG, Neumann B, Ignat'ev N, Hoge B., Angew. Chem. Int. Ed. Engl. 53(2), 2013
PMID: 24288152
Steinhauer S, Stammler HG, Neumann B, Ignat'ev N, Hoge B., Angew. Chem. Int. Ed. Engl. 53(2), 2013
PMID: 24288152
AUTHOR UNKNOWN, Angew. Chem. 126(), 2014
Synthesis of tris- and tetrakis(pentafluoroethyl)silanes.
Steinhauer S, Bader J, Stammler HG, Ignat'ev N, Hoge B., Angew. Chem. Int. Ed. Engl. 53(20), 2014
PMID: 24692241
Steinhauer S, Bader J, Stammler HG, Ignat'ev N, Hoge B., Angew. Chem. Int. Ed. Engl. 53(20), 2014
PMID: 24692241
AUTHOR UNKNOWN, Angew. Chem. 126(), 2014
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
The Bis(pentafluoroethyl)phosphinous acid (C2F5)2POH.
Hoge B, Bader J, Beckers H, Kim YS, Eujen R, Willner H, Ignatiev N., Chemistry 15(14), 2009
PMID: 19219874
Hoge B, Bader J, Beckers H, Kim YS, Eujen R, Willner H, Ignatiev N., Chemistry 15(14), 2009
PMID: 19219874
First solid-state structures of real diorganyl phosphinous acids R2POH (R=CF3, C2F5).
Bader J, Berger RJ, Stammler HG, Mitzel NW, Hoge B., Chemistry 17(48), 2011
PMID: 22052837
Bader J, Berger RJ, Stammler HG, Mitzel NW, Hoge B., Chemistry 17(48), 2011
PMID: 22052837
AUTHOR UNKNOWN, 0
Chambers, 1973
Roddick, Chem. Eng. News 75(), 1997
Kvíčala, J. Fluorine Chem. 113(), 2002
AUTHOR UNKNOWN, 0
Clark, J. Chem. Soc. Chem. Commun. (), 1979
Schleyer, J. Am. Chem. Soc. 106(), 1984
Mareda, J. Am. Chem. Soc. 105(), 1983
AUTHOR UNKNOWN, 0
Boche, Angew. Chem. Int. Ed. Engl. 33(), 1994
AUTHOR UNKNOWN, Angew. Chem. 106(), 1994
[Lithium tert-butylperoxide]12 : Crystal Structure of an Aggregated Oxenoid.
Boche G, Mobus K, Harms K, Lohrenz JCW, Marsch M., Chemistry 2(5), 1996
PMID: 29178227
Boche G, Mobus K, Harms K, Lohrenz JCW, Marsch M., Chemistry 2(5), 1996
PMID: 29178227
Bode, Z. Anorg. Allg. Chem. 621(), 1995
AUTHOR UNKNOWN, 0
Mitzel, J. Am. Chem. Soc. 122(), 2000
Three-membered ring or open chain molecule - (F3C)F2SiONMe2 a model for the alpha-effect in silicon chemistry.
Mitzel NW, Vojinovic K, Frohlich R, Foerster T, Robertson HE, Borisenko KB, Rankin DW., J. Am. Chem. Soc. 127(39), 2005
PMID: 16190736
Mitzel NW, Vojinovic K, Frohlich R, Foerster T, Robertson HE, Borisenko KB, Rankin DW., J. Am. Chem. Soc. 127(39), 2005
PMID: 16190736
AUTHOR UNKNOWN, 0
Ansorge, Angew. Chem. Int. Ed. Engl. 32(), 1993
AUTHOR UNKNOWN, Angew. Chem. 105(), 1993
Winkelhaus, Z. Anorg. Allg. Chem. 639(), 2013
AUTHOR UNKNOWN, 0
Stey, 2004
Structure formation principles and reactivity of organolithium compounds.
Gessner VH, Daschlein C, Strohmann C., Chemistry 15(14), 2009
PMID: 19260001
Gessner VH, Daschlein C, Strohmann C., Chemistry 15(14), 2009
PMID: 19260001
Boche, Angew. Chem. Int. Ed. Engl. 32(), 1993
AUTHOR UNKNOWN, Angew. Chem. 105(), 1993
Müller, Angew. Chem. Int. Ed. Engl. 35(), 1996
AUTHOR UNKNOWN, Angew. Chem. 108(), 1996
AUTHOR UNKNOWN, 0
From a stable dianion to a stable carbenoid.
Cantat T, Jacques X, Ricard L, Le Goff XF, Mezailles N, Le Floch P., Angew. Chem. Int. Ed. Engl. 46(31), 2007
PMID: 17607672
Cantat T, Jacques X, Ricard L, Le Goff XF, Mezailles N, Le Floch P., Angew. Chem. Int. Ed. Engl. 46(31), 2007
PMID: 17607672
AUTHOR UNKNOWN, Angew. Chem. 119(), 2007
Kupper, Organometallics 33(), 2014
Boche, J. Chem. Soc. Chem. Commun. (), 1994
Seebach, Helv. Chim. Acta 63(), 1980
Dolomanov, J. Appl. Cryst. 42(), 2009
A short history of SHELX.
Sheldrick GM., Acta Crystallogr., A, Found. Crystallogr. 64(Pt 1), 2007
PMID: 18156677
Sheldrick GM., Acta Crystallogr., A, Found. Crystallogr. 64(Pt 1), 2007
PMID: 18156677
Salomone, Chem. Sci. 5(), 2014
The Coordination Chemistry of the CF Unit in Fluorocarbons.
Plenio H., Chem. Rev. 97(8), 1997
PMID: 11851493
Plenio H., Chem. Rev. 97(8), 1997
PMID: 11851493
AUTHOR UNKNOWN, 0
Tipton, J. Chem. Phys. 46(), 1967
Beagley, J. Mol. Struct. 71(), 1981
Blanco, J. Mol. Struct. 599(), 2001
Halocarbon and arene coordination of lithium(I) in (1-anilino-3-phenyliminopropenyl)chloro(methyl)aluminium bis
Guzei IA, Radzewich CE, Jordan RF., Acta Crystallogr C 56 (Pt 3)(), 2000
PMID: 10777919
Guzei IA, Radzewich CE, Jordan RF., Acta Crystallogr C 56 (Pt 3)(), 2000
PMID: 10777919
Stalke, J. Chem. Soc. Chem. Commun. (), 1990
AUTHOR UNKNOWN, 0
Tian, Organometallics 24(), 2004
Lustig, Organometallics 22(), 2003
AUTHOR UNKNOWN, 0
Bader, 1990
Popelier, 2000
AUTHOR UNKNOWN, 2007
AUTHOR UNKNOWN, 0
Rankin, 2013
Toward a consistent interpretation of the QTAIM: tortuous link between chemical bonds, interactions, and bond/line paths.
Foroutan-Nejad C, Shahbazian S, Marek R., Chemistry 20(32), 2014
PMID: 24990224
Foroutan-Nejad C, Shahbazian S, Marek R., Chemistry 20(32), 2014
PMID: 24990224
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Stalke, J. Organomet. Chem. 344(), 1988
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 25205058
PubMed | Europe PMC
Suchen in