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A Monomeric Stannabenzene: Synthesis, Structure, and Electronic Properties.
Canon Kaiya1, Katsunori Suzuki1, Makoto Yamashita1
1Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603, Japan.
Angewandte Chemie (International Ed. in English)
|March 30, 2019
Summary
Researchers synthesized and isolated monomeric stannabenzene, a tin-containing benzene analog. Structural and spectroscopic analyses confirm its aromaticity, revealing a planar ring with unsaturated bonds and characteristics typical of aromatic compounds.
Area of Science:
- Organometallic Chemistry
- Aromaticity Studies
Background:
- Aromatic compounds are fundamental in chemistry, typically featuring carbon rings.
- The exploration of heavier heteroatoms within aromatic systems is an ongoing frontier.
Purpose of the Study:
- To synthesize and characterize a tin-containing benzene analog, stannabenzene.
- To investigate the structural, electronic, and aromatic properties of stannabenzene.
Main Methods:
- Synthesis and isolation of monomeric stannabenzene.
- X-ray crystallographic analysis for structural determination.
- Nuclear Magnetic Resonance (NMR) spectroscopy and UV/Vis spectroscopy.
- Electrochemical measurements and calculation of nuclear-independent chemical shifts (NICS).
Main Results:
- Successful synthesis and isolation of monomeric stannabenzene.
- X-ray crystallography confirmed a planar stannabenzene ring with unsaturated Sn-C and C-C bonds and no bond alternation.
- NMR signals and negative NICS values indicated aromatic character.
- UV/Vis spectroscopy and electrochemistry revealed a narrow HOMO-LUMO gap.
Conclusions:
- Stannabenzene exhibits key features characteristic of aromatic compounds.
- This work expands the scope of aromatic systems to include heavier main group elements like tin.
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