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DFT calculations of properties of CF3-carbocations of the thiophene series as key intermediates in the synthesis of novel CF3-thiophenes. / Khoroshilova, O.V.; Boyarskaya, I.A.; Vasilyev, A.V.

In: Tetrahedron, Vol. 168, 134321, 01.12.2024.

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

Harvard

Khoroshilova, OV, Boyarskaya, IA & Vasilyev, AV 2024, 'DFT calculations of properties of CF3-carbocations of the thiophene series as key intermediates in the synthesis of novel CF3-thiophenes', Tetrahedron, vol. 168, 134321. https://doi.org/10.1016/j.tet.2024.134321

APA

Khoroshilova, O. V., Boyarskaya, I. A., & Vasilyev, A. V. (2024). DFT calculations of properties of CF3-carbocations of the thiophene series as key intermediates in the synthesis of novel CF3-thiophenes. Tetrahedron, 168, [134321]. https://doi.org/10.1016/j.tet.2024.134321

Vancouver

Khoroshilova OV, Boyarskaya IA, Vasilyev AV. DFT calculations of properties of CF3-carbocations of the thiophene series as key intermediates in the synthesis of novel CF3-thiophenes. Tetrahedron. 2024 Dec 1;168. 134321. https://doi.org/10.1016/j.tet.2024.134321

Author

Khoroshilova, O.V. ; Boyarskaya, I.A. ; Vasilyev, A.V. / DFT calculations of properties of CF3-carbocations of the thiophene series as key intermediates in the synthesis of novel CF3-thiophenes. In: Tetrahedron. 2024 ; Vol. 168.

BibTeX

@article{a0c776d227134a44bf22690acc35b0b7,
title = "DFT calculations of properties of CF3-carbocations of the thiophene series as key intermediates in the synthesis of novel CF3-thiophenes",
abstract = "Trimethylsilyl ethers of thiophen-2-yl-(trifluoromethyl)methanols undergo multichannel electrophilic transformations under the action of Br{\o}nsted superacid acid CF3SO3H to form a wide range of CF3-substituted thiophene structures. The key cationic intermediates of these transformations are CF3-carbocations. Electronic and orbital characteristics, global electrophilicity indices, and thermodynamic characteristics of these key intermediates have been calculated with a use of the density functional theory (DFT). Experimental data on the reactivity of intermediate cationic species have been explained on the basis of the results of quantum chemical calculations. It has been shown that reactions of the cations with aromatic nucleophiles are mainly ruled by orbital control. {\textcopyright} 2024 Elsevier Ltd",
keywords = "Cations, DFT calculations, Electrophilic aromatic substitution, Thiophenes, Trifluoromethyl carbocations",
author = "O.V. Khoroshilova and I.A. Boyarskaya and A.V. Vasilyev",
note = "Export Date: 4 November 2024 CODEN: TETRA",
year = "2024",
month = dec,
day = "1",
doi = "10.1016/j.tet.2024.134321",
language = "Английский",
volume = "168",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - DFT calculations of properties of CF3-carbocations of the thiophene series as key intermediates in the synthesis of novel CF3-thiophenes

AU - Khoroshilova, O.V.

AU - Boyarskaya, I.A.

AU - Vasilyev, A.V.

N1 - Export Date: 4 November 2024 CODEN: TETRA

PY - 2024/12/1

Y1 - 2024/12/1

N2 - Trimethylsilyl ethers of thiophen-2-yl-(trifluoromethyl)methanols undergo multichannel electrophilic transformations under the action of Brønsted superacid acid CF3SO3H to form a wide range of CF3-substituted thiophene structures. The key cationic intermediates of these transformations are CF3-carbocations. Electronic and orbital characteristics, global electrophilicity indices, and thermodynamic characteristics of these key intermediates have been calculated with a use of the density functional theory (DFT). Experimental data on the reactivity of intermediate cationic species have been explained on the basis of the results of quantum chemical calculations. It has been shown that reactions of the cations with aromatic nucleophiles are mainly ruled by orbital control. © 2024 Elsevier Ltd

AB - Trimethylsilyl ethers of thiophen-2-yl-(trifluoromethyl)methanols undergo multichannel electrophilic transformations under the action of Brønsted superacid acid CF3SO3H to form a wide range of CF3-substituted thiophene structures. The key cationic intermediates of these transformations are CF3-carbocations. Electronic and orbital characteristics, global electrophilicity indices, and thermodynamic characteristics of these key intermediates have been calculated with a use of the density functional theory (DFT). Experimental data on the reactivity of intermediate cationic species have been explained on the basis of the results of quantum chemical calculations. It has been shown that reactions of the cations with aromatic nucleophiles are mainly ruled by orbital control. © 2024 Elsevier Ltd

KW - Cations

KW - DFT calculations

KW - Electrophilic aromatic substitution

KW - Thiophenes

KW - Trifluoromethyl carbocations

UR - https://www.mendeley.com/catalogue/865cce38-88f6-3ab0-b3a5-c0992ec3ad8c/

U2 - 10.1016/j.tet.2024.134321

DO - 10.1016/j.tet.2024.134321

M3 - статья

VL - 168

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

M1 - 134321

ER -

ID: 126693581