Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry

Weisheim E, Reuter C, Heinrichs P, Vishnevskiy Y, Mix A, Neumann B, Stammler H-G, Mitzel NW (2015)
Chemistry - A European Journal 21(35): 12436-12448.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
Directed tridentate Lewis acids based on the 1,3,5-trisilacyclohexane skeleton with three ethynyl groups [CH2Si(Me)(C2H)](3) were synthesised and functionalised by hydroboration with HB(C6F5)(2), yielding the ethenylborane {CH2Si(Me)[C2H2B(C6F5)(2)]}(3), and by metalation with gallium and indium organyls affording {CH2Si(Me)[C2M(R)(2)]}(3) (M=Ga, In, R=Me, Et). In the synthesis of the backbone the influence of substituents (MeO, EtO and iPrO groups at Si) on the orientation of the methyl group was studied with the aim to increase the abundance of the all-cis isomer. New compounds were identified by elemental analyses, multi-nuclear NMR spectroscopy and in some cases by IR spectroscopy. Crystal structures were obtained for cis-trans-[CH2Si(Me)(Cl)](3), all-cis-[CH2Si(Me)(H)](3), all-cis-[CH2Si(Me)(C2H)](3), cis-trans[CH2Si(Me)(C2H)](3) and all-cis-[CH2Si(Me)(C2SiMe3)](3). A gas-phase electron diffraction experiment for all-cis[ CH2Si(Me)(C2H)](3) provides information on the relative stabilities of the all-equatorial and all-axial form; the first is preferred in both solid and gas phase. The gallium-based Lewis acid {CH2Si(Me)[C2Ga(Et)(2)]}(3) was reacted with a tridentate Lewis base (1,3,5-trimethyl-1,3,5-triazacyclohexane) in an NMR titration experiment. The generated host-guest complexes involved in the equilibria during this reaction were identified by DOSY NMR spectroscopy by comparing measured diffusion coefficients with those of the suitable reference compounds of same size and shape.
Erscheinungsjahr
Zeitschriftentitel
Chemistry - A European Journal
Band
21
Zeitschriftennummer
35
Seite
12436-12448
ISSN
PUB-ID

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Weisheim E, Reuter C, Heinrichs P, et al. Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry. Chemistry - A European Journal. 2015;21(35):12436-12448.
Weisheim, E., Reuter, C., Heinrichs, P., Vishnevskiy, Y., Mix, A., Neumann, B., Stammler, H. - G., et al. (2015). Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry. Chemistry - A European Journal, 21(35), 12436-12448. doi:10.1002/chem.201501683
Weisheim, E., Reuter, C., Heinrichs, P., Vishnevskiy, Y., Mix, A., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2015). Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry. Chemistry - A European Journal 21, 12436-12448.
Weisheim, E., et al., 2015. Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry. Chemistry - A European Journal, 21(35), p 12436-12448.
E. Weisheim, et al., “Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry”, Chemistry - A European Journal, vol. 21, 2015, pp. 12436-12448.
Weisheim, E., Reuter, C., Heinrichs, P., Vishnevskiy, Y., Mix, A., Neumann, B., Stammler, H.-G., Mitzel, N.W.: Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry. Chemistry - A European Journal. 21, 12436-12448 (2015).
Weisheim, Eugen, Reuter, Christian, Heinrichs, Peter, Vishnevskiy, Yury, Mix, Andreas, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “Tridentate Lewis Acids Based on 1,3,5-Trisilacyclohexane Backbones and an Example of Their Host-Guest Chemistry”. Chemistry - A European Journal 21.35 (2015): 12436-12448.

6 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Tridentate Lewis-acids based on triphenylsilane.
Tomaschautzky J, Neumann B, Stammler HG, Mix A, Mitzel NW., Dalton Trans 46(5), 2017
PMID: 28098286
Fluoride complexation by bidentate silicon Lewis acids.
Horstmann J, Niemann M, Berthold K, Mix A, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 46(6), 2017
PMID: 28106199
From Bidentate Gallium Lewis Acids to Supramolecular Complexes.
Horstmann J, Hyseni M, Mix A, Neumann B, Stammler HG, Mitzel NW., Angew Chem Int Ed Engl 56(22), 2017
PMID: 28418175
Organotin-based receptors for anions and ion pairs.
Naseer MM, Jurkschat K., Chem Commun (Camb) 53(58), 2017
PMID: 28580478
Tridentate Lewis acids with phenyl substituted 1,3,5-trisilacyclohexane backbones.
Weisheim E, Bücker L, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 45(1), 2016
PMID: 26599621
Silicon- and Tin-Containing Open-Chain and Eight-Membered-Ring Compounds as Bicentric Lewis Acids toward Anions.
Wendji AS, Dietz C, Kühn S, Lutter M, Schollmeyer D, Hiller W, Jurkschat K., Chemistry 22(1), 2016
PMID: 26616743

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