Enhancing the Antiaromaticity of s-Indacene through Naphthothiophene Fusion
| العنوان: | Enhancing the Antiaromaticity of s-Indacene through Naphthothiophene Fusion |
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| المؤلفون: | Joshua E. Barker, Lev N. Zakharov, Michael M. Haley, Gabrielle I. Warren |
| المصدر: | Organic Letters. 23:5012-5017 |
| بيانات النشر: | American Chemical Society (ACS), 2021. |
| سنة النشر: | 2021 |
| مصطلحات موضوعية: | Molecular orbital energy, Fusion, medicine.diagnostic_test, 010405 organic chemistry, Chemistry, Organic Chemistry, Aromaticity, Nuclear magnetic resonance spectroscopy, 010402 general chemistry, 01 natural sciences, Biochemistry, 0104 chemical sciences, Crystallography, Spectrophotometry, medicine, Molecule, Physical and Theoretical Chemistry, Cyclic voltammetry, Antiaromaticity |
| الوصف: | Addressing the instability of antiaromatic compounds often involves protection with bulky groups and/or fusion of aromatic rings, thus decreasing paratropicity. We report four naphthothiophene-fused s-indacene isomers, one of which is more antiaromatic than parent s-indacene. This surprising result is examined computationally through nucleus-independent chemical shift XY calculations and experimentally via nuclear magnetic resonance spectroscopy, X-ray crystallography, ultraviolet-visible spectrophotometry, and cyclic voltammetry, with the latter two indicating that this molecule possesses the lowest highest occupied molecular orbital-lowest unoccupied molecular orbital energy gap observed for heterocycle-fused s-indacene. |
| تدمد: | 1523-7052 1523-7060 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::f4fc8774efc29ea6a982fc8f9fc5e0a1 https://doi.org/10.1021/acs.orglett.1c01514 |
| حقوق: | CLOSED |
| رقم الأكسشن: | edsair.doi...........f4fc8774efc29ea6a982fc8f9fc5e0a1 |
| قاعدة البيانات: | OpenAIRE |
Find this issue from the American Chemical Society | تدمد: | 15237052 15237060 |
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