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Data · dataset · 2026

Raw data for "Isolation of Base-Stabilized 1,4-Disilaquinones"

Listed in TUDOdata

PROJECT DESCRIPTION: Despite the importance of quinones in organic synthesis and materials chemistry, their silicon analogues remain largely unexplored until to date.

Description

Herein, we report the synthesis of two base-stabilized 1,4-disilaquinones through dimerization of ketenyl-substituted silylenes. These silylenes were obtained in high yields by reaction of two differently substituted metalated ketenes with the amidinato-stabilized chloro silylene (PhC(NtBu)2SiCl).

X-ray crystallography combined with density functional theory (DFT) calculations revealed a planar, but unsymmetrical structure of the disilaquinone core, arising from its unusual bonding situation. The central heterocyclic motif is best described as a resonance hybrid of three principal forms: a silaquinone-type structure, or as a dimer of two enolates and carbanionic ketones, respectively. Despite its non-aromatic character, the disilaquinone core exhibits remarkable thermal and chemical stability, showing no tendency toward ring opening.

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Although unreactive toward nucleophiles, treatment with Lewis or Brønsted acids perturbs the π-electron density but preserves the integrity of the six-membered ring framework. DATASET DESCRIPTION: Single folders were created for all described molecules and reactivities and named in accordance with the manuscript. The folders contain a substructure with NMR spectra (raw data directory) for all molecules, and additional IR (.ipsd, .txt and .pdf), EA (.pdf) and computational (.out) data for compounds (3a, 3b).

Programs that can be used to open the data: IR: Can be opened with the LabSolutions software (an open source alternative would be the software "OpenChrom"). NMR: Can be opened with MestReNova EA: Can be opened with various pdf Readers (e.g. "Adobe Acrobat Reader" or "PDF24 Reader") Computations: Can be opened with various text-editing programs (e.g. "Windows Editor" or "Notepad++")

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Catalogue records · 1

Topics

Stated by source
Chemistry
Inferred from text
Density functional theory 75% · Organic chemistry 71%
Provenance · 1 source records, 14 field assertions
SourceKeyLast seenRaw
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