Investigation of the Dynamic Behavior of Bisumanenyl | Zendy

Shrestha Binod Babu | Zendy; Karanjit Sangita | Zendy; Higashibayashi Shuhei | Zendy; Amaya Toru | Zendy; Hirao Toshikazu | Zendy; Sakurai Hidehiro | Zendy

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Investigation of the Dynamic Behavior of Bisumanenyl

Author(s) -

Shrestha Binod Babu,

Karanjit Sangita,

Higashibayashi Shuhei,

Amaya Toru,

Hirao Toshikazu,

Sakurai Hidehiro

Publication year - 2015

Publication title -

asian journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.846

H-Index - 44

eISSN - 2193-5815

pISSN - 2193-5807

DOI - 10.1002/ajoc.201402226

Subject(s) - diastereomer , chemistry , conformational isomerism , rotation (mathematics) , inversion (geology) , computational chemistry , stereochemistry , crystallography , molecule , organic chemistry , paleontology , geometry , mathematics , structural basin , biology

The behavior of bisumanenyl is dynamic as a result of inversion of each of its sumanene bowls and rotation between the two bowls. This behavior was fully elucidated by a combination of NMR experiments and density functional theory calculations. The MM (or PP ) and MP diastereomers are in thermodynamic equilibrium at room temperature and the MM ( PP ) diastereomer is 1.4–1.9 kcal mol −1 more stable than MP diastereomer. The calculated energy for inversion between the two forms of the bowl is 19.2 kcal mol −1 . The MM ( PP ) and MP diastereomers have two rotational stable conformers that rapidly interconvert as a result of the low rotational energy barriers, which were calculated to be 3.9 and 8.9 kcal mol −1 , respectively.

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