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Synthesis and Thermal Investigations of Eleven-Membered Ring Systems Containing One of the Heavier Group 14 Element Atoms Si, Ge, and Sn

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Institute for Analytical and Organic Chemistry, University of Bremen, Leobener Straße 7, D-28359 Bremen, Germany
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MAPEX Center for Materials and Processes, University of Bremen, Bibliothekstraße 1, D-28359 Bremen, Germany
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Institute of Inorganic Chemistry and Crystallography, University of Bremen, Leobener Straße 7, 28359 D-Bremen, Germany
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Institute for Physical and Theoretical Chemistry, University of Bremen, Leobener Str. 7, D-28359 Bremen, Germany
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Authors to whom correspondence should be addressed.
Academic Editor: Bagrat A. Shainyan
Molecules 2020, 25(2), 283; https://doi.org/10.3390/molecules25020283
Received: 19 November 2019 / Revised: 17 December 2019 / Accepted: 24 December 2019 / Published: 10 January 2020
(This article belongs to the Special Issue Structure and Conformational Analysis of Heterocyclic Compounds)
Unique eleven-membered rings containing silicon, germanium, and tin were synthesized in good yields by the reactions of the corresponding 1,2-bis((2-bromothiophen-3-yl)methoxy)benzenes with (C6H5)2ECl2 where E = Sn, Ge, Si. The Sn and Ge congeners were crystallized, but the conformers that these rings crystallized in, were quite different. As confirmed by Density Functional Theory (DFT) calculations, (C28H22O2S2Sn) assumes a unique crystal structure that leaves more room around the tetrel atom as compared to the crystal structure of the corresponding Ge compound. In the latter, the central cavity is quite open, whereas in the former, one of the methylene groups can fold inwards. Another consequence is the influence on the planes of the aromatic rings flanking the heterocycle. In the Ge case, the benzene ring is folded away from the central cavity, whereas in the Sn case, it is almost parallel to the imaginary axis through the center of the ring. Thermal analysis investigations (TGA and DSC methods) of these eleven-membered rings suggested the loss of a phenyl group in the first decomposition step. The decomposition temperature decreased from the Si containing heterocycle to Ge and was lowest for the Sn containing heterocycle. View Full-Text
Keywords: tetrels; group 14 elements; 11-membered rings; conformation tetrels; group 14 elements; 11-membered rings; conformation
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MDPI and ACS Style

Eleya, N.; Appiah, C.; Lork, E.; Gogolin, M.; Gesing, T.M.; Stauch, T.; Staubitz, A. Synthesis and Thermal Investigations of Eleven-Membered Ring Systems Containing One of the Heavier Group 14 Element Atoms Si, Ge, and Sn. Molecules 2020, 25, 283.

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