Abstract
The effect of benzannelation on the conformational flexibility of the six-membered 1,2- and 1,4-dihydroaromatic rings containing no saturated carbon atoms is studied by the ab initio HF/6-31G(d, p) method. It is shown that replacement of the C=C bond by the benzene ring leads to enhanced conformational flexibility of the ring due to weaker conjugation interactions involving the bridging carbonyl group or the heteroatom. The dihydro ring remains flexible even when included in the tetracene fragment. In all cases, the 1,2-dihydroaromatic rings are less rigid than their 1,4-dihydroanalogs.
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Shishkin, O.V., Kovalevskii, A.Y. Conformational Flexibility of Benzannelated Derivatives of Six-Membered 1,2- and 1,4-Dihydroaromatic Rings Containing No Saturated Carbon Atoms. Journal of Structural Chemistry 42, 550–554 (2001). https://doi.org/10.1023/A:1013177422796
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DOI: https://doi.org/10.1023/A:1013177422796