The Conformational Behaviour of Fluorinated Tetrahydrothiopyran

Nwar Egbaria; Mohamed Agbaria; Veniamin A. Borin; Roy E. Hoffman; Benny Bogoslavsky; Igor Schapiro; Zackaria Nairoukh

doi:10.1002/chem.202402260

The Conformational Behaviour of Fluorinated Tetrahydrothiopyran

Nwar Egbaria, Mohamed Agbaria, Veniamin A. Borin, Roy E. Hoffman, Benny Bogoslavsky, Igor Schapiro^*, Zackaria Nairoukh^*

^*Corresponding author for this work

Institute of Chemistry

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

Abstract

We present a comprehensive study on the conformational behavior of diversely substituted 4-fluorotetrahydrothiopyran derivatives. Through quantum chemical simulations including DFT as well as NBO and NPA analysis, we elucidate the pivotal role of electrostatic interactions, occasionally complemented by hyperconjugative interactions, in stabilizing axial fluorine conformers. Less polar conformers were occasionally obtained, attributed to the interplay of electrostatic and hyperconjugative interactions. Experimental validation through NMR spectroscopy aligns with the computational analysis, thus providing a coherent understanding of the structural dynamics of these compounds.

Original language	English
Article number	e202402260
Journal	Chemistry - A European Journal
Volume	30
Issue number	55
DOIs	https://doi.org/10.1002/chem.202402260
State	Published - 1 Oct 2024

Bibliographical note

Publisher Copyright:
© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.

Keywords

Conformational behavior
DFT
Fluorine
NMR analysis
Tetrahydrothiopyran

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abstract = "We present a comprehensive study on the conformational behavior of diversely substituted 4-fluorotetrahydrothiopyran derivatives. Through quantum chemical simulations including DFT as well as NBO and NPA analysis, we elucidate the pivotal role of electrostatic interactions, occasionally complemented by hyperconjugative interactions, in stabilizing axial fluorine conformers. Less polar conformers were occasionally obtained, attributed to the interplay of electrostatic and hyperconjugative interactions. Experimental validation through NMR spectroscopy aligns with the computational analysis, thus providing a coherent understanding of the structural dynamics of these compounds.",

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AU - Borin, Veniamin A.

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AU - Bogoslavsky, Benny

AU - Schapiro, Igor

AU - Nairoukh, Zackaria

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KW - Conformational behavior

KW - DFT

KW - Fluorine

KW - NMR analysis

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The Conformational Behaviour of Fluorinated Tetrahydrothiopyran

Abstract

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Keywords

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