Investigation of the dynamic behavior of bisumanenyl

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

doi:10.1002/ajoc.201402226

Investigation of the dynamic behavior of bisumanenyl

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

Research output: Contribution to journal › Article › peer-review

6 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 language	English
Pages (from-to)	62-68
Number of pages	7
Journal	Asian Journal of Organic Chemistry
Volume	4
Issue number	1
DOIs	https://doi.org/10.1002/ajoc.201402226
Publication status	Published - 2015 Jan 1
Externally published	Yes

Keywords

Bisumanenyl
Bowl inversion
Conformation analysis
Polyaromatic hydrocarbons
Sumanene

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.201402226

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title = "Investigation of the dynamic behavior of bisumanenyl",

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.",

keywords = "Bisumanenyl, Bowl inversion, Conformation analysis, Polyaromatic hydrocarbons, Sumanene",

author = "Shrestha, {Binod Babu} and Sangita Karanjit and Shuhei Higashibayashi and Toru Amaya and Toshikazu Hirao and Hidehiro Sakurai",

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T1 - Investigation of the dynamic behavior of bisumanenyl

AU - Shrestha, Binod Babu

AU - Karanjit, Sangita

AU - Higashibayashi, Shuhei

AU - Amaya, Toru

AU - Hirao, Toshikazu

AU - Sakurai, Hidehiro

PY - 2015/1/1

Y1 - 2015/1/1

N2 - 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.

AB - 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.

KW - Bisumanenyl

KW - Bowl inversion

KW - Conformation analysis

KW - Polyaromatic hydrocarbons

KW - Sumanene

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Investigation of the dynamic behavior of bisumanenyl

Abstract

Keywords

ASJC Scopus subject areas

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