A Monomeric Stannabenzene: Synthesis, Structure, and Electronic Properties

A tin‐containing benzene, stannabenzene, was synthesized and isolated as a monomeric form. The X‐ray crystallographic analysis revealed the planar structure of the stannabenzene ring and unsaturated Sn−C and C−C bonds without bond alternation. Low‐field shifted NMR signals and negative nuclear‐indep...

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Bibliographic Details
Published inAngewandte Chemie Vol. 131; no. 23; pp. 7831 - 7834
Main Authors Kaiya, Canon, Suzuki, Katsunori, Yamashita, Makoto
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 03.06.2019
Subjects
Aromatic compounds
Benzene
Benzol
Chemistry
Crystallography
Electrochemistry
Gruppe-14-Elemente
Molecular orbitals
NMR
Nuclear magnetic resonance
Organic chemistry
Organozinn-Verbindungen
Planar structures
Schwere Atome
Spectroscopy
Stannabanzol
Tin
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Summary:A tin‐containing benzene, stannabenzene, was synthesized and isolated as a monomeric form. The X‐ray crystallographic analysis revealed the planar structure of the stannabenzene ring and unsaturated Sn−C and C−C bonds without bond alternation. Low‐field shifted NMR signals and negative nuclear‐independent chemical shifts (NICS) values are in agreement with the features of aromatic compounds. The narrow HOMO–LUMO gap of stannabenzene has been revealed by UV/Vis spectroscopy and electrochemistry. Da ist Zinn im Ring drin: Ein Stannabenzol wurde in monomerer Form isoliert. Röntgenkristallographische Analysen zeigten eine planare Struktur und ungesättigte Bindungen im Stannabenzolring, Merkmale einer aromatischen Verbindung. Die schmale HOMO‐LUMO‐Lücke des Rings wurde durch UV/Vis‐Spektroskopie, Elektrochemie und DFT‐Berechnungen bestätigt.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201902639