The Conformational Behaviour of Fluorinated Tetrahydrothiopyran

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

doi:https://doi.org/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

Institute of Chemistry

The Hebrew University of Jerusalem

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

Keywords

Conformational behavior
DFT
Fluorine
NMR analysis
Tetrahydrothiopyran

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Organic Chemistry

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https://doi.org/10.1002/chem.202402260

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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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T1 - The Conformational Behaviour of Fluorinated Tetrahydrothiopyran

AU - Egbaria, Nwar

AU - Agbaria, Mohamed

AU - Borin, Veniamin A.

AU - Hoffman, Roy E.

AU - Bogoslavsky, Benny

AU - Schapiro, Igor

AU - Nairoukh, Zackaria

PY - 2024/10/1

Y1 - 2024/10/1

N2 - 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.

AB - 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.

KW - Conformational behavior

KW - DFT

KW - Fluorine

KW - NMR analysis

KW - Tetrahydrothiopyran

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DO - https://doi.org/10.1002/chem.202402260

M3 - مقالة

C2 - 38989892

SN - 0947-6539

VL - 30

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 55

M1 - e202402260

ER -

The Conformational Behaviour of Fluorinated Tetrahydrothiopyran

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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