A Monomeric Stannabenzene: Synthesis, Structure, and Electronic Properties

• Published in: Angewandte Chemie International Edition Vol. 58; no. 23; pp. 7749 - 7752
• Main Authors: Kaiya, Canon, Suzuki, Katsunori, Yamashita, Makoto
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 03.06.2019; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Aromatic compounds; Benzene; Chemistry; Chemistry, Multidisciplinary; Crystallography; Electrochemistry; Group 14 elements; heavy atom; Molecular orbitals; NMR; Nuclear magnetic resonance; Organic chemistry; organotin; Physical Sciences; Planar structures; Science & Technology; Spectroscopy; stannabenzene; Tin; SILABENZENE; stannabenzene; ORDER REGULAR APPROXIMATION; organotin; COMPOUND; BONDS; heavy atom; REACTIVITY; CHEMISTRY; GENERATION; Group 14 elements; benzene
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201902639

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. Tin in: A tin‐containing benzene, stanna‐benzene, was isolated as a monomeric form. X‐ray crystallographic analysis revealed the planar structure and unsaturated bonds of the stannabenzene ring in agreement with the features of aromatic compound. The narrow HOMO–LUMO gap of stannabenzene ring was confirmed by UV/Vis spectroscopy, electrochemistry, and DFT calculations.