Substituent effects on the selectivity of ambimodal [6+4]/[4+2] cycloaddition

Gu, Wenhao; Zhang, John Z.H.

doi:10.1039/d3cp06320h

Phys. Chem. Chem. Phys.

2024

DOI: 10.1039/d3cp06320h

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Substituent effects on the selectivity of ambimodal [6+4]/[4+2] cycloaddition

Wenhao Gu,

John Z.H. Zhang

Abstract: In this work, we report the density functional theory (DFT) study and the dynamical trajectory study of substituent effects on the ambimodal [6+4]/[4+2] cycloaddition proposed in the 1,3,5,10,12-Cycloheptadecapentaene, referred to...

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Temperature effects on the branching dynamics in the model ambimodal (6 + 4)/(4 + 2) intramolecular cycloaddition reaction

Murakami,

Hayashi,

Kikuma

et al. 2024

J Comput Chem

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C14H20 (tetradecapentaene) is a simple model system exhibiting post transition‐state behavior, wherein both the (6 + 4) and (4 + 2) cycloaddition products are formed from one ambimocal transition state structure. We studied the bifurcation dynamics starting from the two ambimodal transition state structures, the chair‐form and boat‐form, using the quasi‐classical trajectory, classical molecular dynamics, and ring‐polymer molecular dynamics methods on the parameter‐optimized semiempirical GFN2‐xTB potential energy surface. It was found that the calculated branching fractions differ between the chair‐form and boat‐form due to the different nature in the IRC pathways. We also investigated the effects of temperature on bifurcation dynamics and found that, at higher temperatures, trajectories stay longer in the intermediate region of the potential energy surface.

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Temperature effects on the branching dynamics in the model ambimodal (6 + 4)/(4 + 2) intramolecular cycloaddition reaction

Murakami,

Hayashi,

Kikuma

et al. 2024

J Comput Chem

View full text Add to dashboard Cite

show abstract

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Substituent effects on the selectivity of ambimodal [6+4]/[4+2] cycloaddition

Abstract: In this work, we report the density functional theory (DFT) study and the dynamical trajectory study of substituent effects on the ambimodal [6+4]/[4+2] cycloaddition proposed in the 1,3,5,10,12-Cycloheptadecapentaene, referred to...

Cited by 1 publication

References 50 publications

Temperature effects on the branching dynamics in the model ambimodal (6 + 4)/(4 + 2) intramolecular cycloaddition reaction

Temperature effects on the branching dynamics in the model ambimodal (6 + 4)/(4 + 2) intramolecular cycloaddition reaction

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