Investigation of the dynamic behavior of bisumanenyl

Binod Babu Shrestha, Sangita Karanjit, Shuhei Higashibayashi, Toru Amaya, Toshikazu Hirao, Hidehiro Sakurai

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

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 1.4-1.9kcalmol-1 more stable than MP diastereomer. The calculated energy for inversion between the two forms of the bowl is 19.2kcalmol-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 8.9kcalmol-1, respectively.

Original languageEnglish
Pages (from-to)62-68
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume4
Issue number1
DOIs
Publication statusPublished - 2015 Jan 1
Externally publishedYes

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Energy barriers
Density functional theory
Nuclear magnetic resonance
Thermodynamics
Experiments
Temperature
sumanene

Keywords

  • Bisumanenyl
  • Bowl inversion
  • Conformation analysis
  • Polyaromatic hydrocarbons
  • Sumanene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Investigation of the dynamic behavior of bisumanenyl. / Shrestha, Binod Babu; Karanjit, Sangita; Higashibayashi, Shuhei; Amaya, Toru; Hirao, Toshikazu; Sakurai, Hidehiro.

In: Asian Journal of Organic Chemistry, Vol. 4, No. 1, 01.01.2015, p. 62-68.

Research output: Contribution to journalArticle

Shrestha, BB, Karanjit, S, Higashibayashi, S, Amaya, T, Hirao, T & Sakurai, H 2015, 'Investigation of the dynamic behavior of bisumanenyl', Asian Journal of Organic Chemistry, vol. 4, no. 1, pp. 62-68. https://doi.org/10.1002/ajoc.201402226
Shrestha, Binod Babu ; Karanjit, Sangita ; Higashibayashi, Shuhei ; Amaya, Toru ; Hirao, Toshikazu ; Sakurai, Hidehiro. / Investigation of the dynamic behavior of bisumanenyl. In: Asian Journal of Organic Chemistry. 2015 ; Vol. 4, No. 1. pp. 62-68.
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