Enhancing the Antiaromaticity of s-Indacene through Naphthothiophene Fusion
| Autor: | Joshua E. Barker, Lev N. Zakharov, Michael M. Haley, Gabrielle I. Warren |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
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 |
| Zdroj: | Organic Letters. 23:5012-5017 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.1c01514 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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