International Journal of Quantum Chemistry, volume 120, issue 9
Quantum‐chemical models of KOH(KOBu t )/DMSO superbasic systems and mechanisms of base‐promoted acetylene reactions
Publication type: Journal Article
Publication date: 2020-01-24
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.2
ISSN: 00207608, 1097461X
Physical and Theoretical Chemistry
Atomic and Molecular Physics, and Optics
Condensed Matter Physics
Abstract
The mechanisms of fundamental base-promoted acetylene reactions, namely, nucleophilic addition to the triple C ≡ C bond (vinylation) and nucleophilic addition of acetylenic carbanion to a carbonyl group (ethynylation), are addressed using three models of different complexity—pentasolvate, monosolvate, and anionic—which describe the catalytic superbasic systems MOH(OBut)/DMSO (suspensions of alkali hydroxides or tert-butoxides in dimethyl sulfoxide). The above acetylene reactions and sequential transformations of reagents arranged by the superbasic center are modeled within the framework of the most complete pentasolvate model, in which the superbase is represented by the KOH·5DMSO (KOBut·5DMSO) complexes. We have developed approaches to the construction of simplified models (monosolvate and anionic) to describe transformations in complex systems. The mechanisms of cascade assemblies of 6,8-dioxabicyclo[3.2.1]octanes, cyclopentenones, and furan cycles from ketones and acetylenes in the superbasic environment are investigated using a uniform B2PLYP/6-311+G**//B3LYP/6-31+G* approach, and the energy profiles of these different carbo- and heterocycles are analyzed.
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Vitkovskaya N. et al. Quantum‐chemical models of KOH(KOBu t )/DMSO superbasic systems and mechanisms of base‐promoted acetylene reactions // International Journal of Quantum Chemistry. 2020. Vol. 120. No. 9.
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Vitkovskaya N., Orel V. B., Kobychev V., Bobkov A. S., Absalyamov D., Trofimov B. A. Quantum‐chemical models of KOH(KOBu t )/DMSO superbasic systems and mechanisms of base‐promoted acetylene reactions // International Journal of Quantum Chemistry. 2020. Vol. 120. No. 9.
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TY - JOUR
DO - 10.1002/qua.26158
UR - https://doi.org/10.1002%2Fqua.26158
TI - Quantum‐chemical models of KOH(KOBu t )/DMSO superbasic systems and mechanisms of base‐promoted acetylene reactions
T2 - International Journal of Quantum Chemistry
AU - Vitkovskaya, Nadezhda
AU - Orel, Vladimir B
AU - Kobychev, Vladimir
AU - Bobkov, A. S.
AU - Absalyamov, Damir
AU - Trofimov, B. A.
PY - 2020
DA - 2020/01/24 00:00:00
PB - Wiley
IS - 9
VL - 120
SN - 0020-7608
SN - 1097-461X
ER -
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@article{2020_Vitkovskaya,
author = {Nadezhda Vitkovskaya and Vladimir B Orel and Vladimir Kobychev and A. S. Bobkov and Damir Absalyamov and B. A. Trofimov},
title = {Quantum‐chemical models of KOH(KOBu t )/DMSO superbasic systems and mechanisms of base‐promoted acetylene reactions},
journal = {International Journal of Quantum Chemistry},
year = {2020},
volume = {120},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002%2Fqua.26158},
number = {9},
doi = {10.1002/qua.26158}
}