Abstract
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.
Highlights
The chemistry of heterocyclic systems that contain heavier group 14 elements has received wide interest because of their special properties and reactivity [1,2,3]
The tetrel series offers a unique probe for assessing these factors as there can be which typically show ring strain, these two factors are likely to be pivotal for ring conformation and expected be relatively little series electronic contribution
We describe in detail how the tetrel substitution affects the thermal properties of the detail how the tetrel substitution affects the thermal properties of the ring, with regards toring, their with ring regards to their ring stability and their melting behavior, and confirm the results using
Summary
The chemistry of heterocyclic systems that contain heavier group 14 elements has received wide interest because of their special properties and reactivity [1,2,3]. The tetrel series offers a unique probe for assessing these factors as there can be which typically show ring strain, these two factors are likely to be pivotal for ring conformation and expected be relatively little series electronic contribution Some these questions have been addressed ring strainto[15,16,17,18]. The tetrel offers a unique probe forofassessing these factors as there can be by us for other group element compounds [19], regarding their thermal properties expected to be relatively little electronic contribution. Some of these questions have been addressedand by conformational influences on the final structure. Functional calculationsTheory [20,21].(DFT) calculations [20,21]
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