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The X\u2010ray crystallographic analysis revealed the planar structure of the stannabenzene ring and unsaturated Sn\u2212C and C\u2212C bonds without bond alternation. Low\u2010field shifted NMR signals and negative nuclear\u2010independent chemical shifts (NICS) values are in agreement with the features of aromatic compounds. The narrow HOMO\u2013LUMO gap of stannabenzene has been revealed by UV\/Vis spectroscopy and electrochemistry.<\/jats:p>","DOI":"10.1002\/anie.201902639","type":"journal-article","created":{"date-parts":[[2019,3,29]],"date-time":"2019-03-29T08:37:07Z","timestamp":1553848627000},"page":"7749-7752","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["A Monomeric Stannabenzene: Synthesis, Structure, and Electronic Properties"],"prefix":"10.1002","volume":"58","author":[{"given":"Canon","family":"Kaiya","sequence":"first","affiliation":[{"name":"Department of Molecular and Macromolecular Chemistry Graduate School of Engineering Nagoya University  Furo-cho Chikusa-ku Nagoya 464-8603 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7971-5863","authenticated-orcid":false,"given":"Katsunori","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Department of Molecular and Macromolecular Chemistry Graduate School of Engineering Nagoya University  Furo-cho Chikusa-ku Nagoya 464-8603 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3665-5311","authenticated-orcid":false,"given":"Makoto","family":"Yamashita","sequence":"additional","affiliation":[{"name":"Department of Molecular and Macromolecular Chemistry Graduate School of Engineering Nagoya University  Furo-cho Chikusa-ku Nagoya 464-8603 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,5,2]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/9780470669266"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar020093k"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.77.429"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar50124a005"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1007\/BFb0039199"},{"key":"e_1_2_2_7_1","unstructured":"\u00a0"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(20000204)39:3<634::AID-ANIE634>3.0.CO;2-#"},{"key":"e_1_2_2_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(20000204)112:3<648::AID-ANGE648>3.0.CO;2-3"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja000309i"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/jccs.200800073"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja072759h"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0dt00115e"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8DT03081B"},{"key":"e_1_2_2_14_1","unstructured":"\u00a0"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0262941"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/om501204u"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.20160269"},{"key":"e_1_2_2_18_2","author":"Sugahara T.","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_2_19_1","unstructured":"\u00a0"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/om100382n"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8DT02994F"},{"key":"e_1_2_2_22_1","unstructured":"\u00a0"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700801"},{"key":"e_1_2_2_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201700801"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201804858"},{"key":"e_1_2_2_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja057531d"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.8b00938"},{"key":"e_1_2_2_27_1","unstructured":"\u00a0"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja504771d"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.5b00310"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC08397A"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b08714"},{"key":"e_1_2_2_32_1","unstructured":"Similar to the germanium case we tried to synthesize stannabenzene by the reaction of3with two equivalents of MesLi. However we could not isolate the stannabenzene."},{"key":"e_1_2_2_33_1","unstructured":"This reaction would contain a cyclic stannylene as a reaction intermediate followed by oxidation of SnIIto SnIV. To obtain a high yield of3 three equivalents of SnCl2were required. In contrast reaction with one or two equivalents of SnCl2gave significantly lower yield of3 indicating an excess amount of SnCl2was effective. Although the detailed oxidation mechanism for the formation of3was not clear SnCl2might be one of the plausible chlorination sources."},{"key":"e_1_2_2_34_1","unstructured":"\u00a0"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100133q"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198705461"},{"key":"e_1_2_2_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19870990607"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00044a005"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/b512097g"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200701277"},{"key":"e_1_2_2_40_1","volume-title":"Aromaticity and Antiaromaticity; Electronic and Structural Aspects","author":"Minkin V. J.","year":"1994"},{"key":"e_1_2_2_41_1","unstructured":"2Jand2Jcould not be resolved due to overlapping of the satellite signals."},{"key":"e_1_2_2_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/0079-6565(79)80006-0"},{"key":"e_1_2_2_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/0470857188.ch6"},{"key":"e_1_2_2_44_1","unstructured":"The broadening of absorption band was observed. Although the reason was not clear at the present stage the conformational change of stannabenzene ando-tol moiety by rotation might be plausible reason."},{"key":"e_1_2_2_45_1","unstructured":"Details of the calculations are given in the Supporting Information. We also performed structure optimization of1-Snwithout symmetrical restriction to reproduce almost identicalC1structure to theCssymmetrical structure with identical SCF energy. The corresponding triplet state was also structurally optimized however the energy of triplet state was estimated to be 26.3\u2005kcal\u2009mol\u22121higher than that of the singlet state."},{"key":"e_1_2_2_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr030088"},{"key":"e_1_2_2_47_1","unstructured":"\u00a0"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.472460"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.478680"},{"key":"e_1_2_2_50_1","unstructured":"By the gauge-independent atomic orbital (GIAO) calculation using effective core potential such as LanL2DZ for Sn the119Sn NMR chemical shift was estimated to be 1.9\u2005ppm being different from experimentally observed value. Thus we used all-electron basis set with relativistic Hamiltonian for NICS by GIAO calculation. In this calculation the119Sn chemical shift of1-Snwas calculated to be at low field region 580.7\u2005ppm being similar to the experimentally observed value."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201902639","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201902639","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201902639","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/am-pdf\/10.1002\/anie.201902639","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201902639","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,6]],"date-time":"2023-09-06T21:07:05Z","timestamp":1694034425000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201902639"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,5,2]]},"references-count":53,"journal-issue":{"issue":"23","published-print":{"date-parts":[[2019,6,3]]}},"alternative-id":["10.1002\/anie.201902639"],"URL":"https:\/\/doi.org\/10.1002\/anie.201902639","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,5,2]]},"assertion":[{"value":"2019-03-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-05-02","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}