The Kinetic Solvent Effect on 1,3-Dipolar Cycloaddition of 2,2,5,5-Tetramethyl-3-imidazoline-3-oxide-1-oxyl

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The Kinetic Solvent Effect on 1,3-Dipolar Cycloaddition of 2,2,5,5-Tetramethyl-3-imidazoline-3-oxide-1-oxyl. / Cherkasov, Sergey A.; Kaletina, Polina M.; Polienko, Yuliya F. et al.

In: ChemPlusChem, Vol. 87, No. 7, e202200119, 07.2022.

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

BibTeX

@article{b8032d77e063405e94b99e9699b2b2fc,

title = "The Kinetic Solvent Effect on 1,3-Dipolar Cycloaddition of 2,2,5,5-Tetramethyl-3-imidazoline-3-oxide-1-oxyl",

abstract = "The use of 2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl (1) as a controlling agent in Nitroxide Mediated Polymerization allows for activation of alkoxyamine homolysis by 1,3-dipolar cycloaddition of a vinyl monomer [Edeleva et al. Chem. Commun. 2019, 55, 190–193]. Polymerization can be carried out in a medium with different polarity and hydrogen bonding capacity which affects the rate of 1,3-dipolar cycloaddition reaction. In the present study, the solvent effect on the rate of this reaction was investigated by the electron paramagnetic resonance and density functional theory for the six different dipolarophiles, e. g. styrene, n-butyl acrylate, acrylonitrile, methyl vinyl ketone, maleic anhydride, and N-phenyl maleimide. The rate of 1,3 dipolar cycloaddition of non-polar styrene was found to be slightly dependent on solvent, while one order of magnitude decrease in rate coefficient is observed for other dipolarophiles when going from hexane to methanol.",

keywords = "1,3-dipolar cycloaddition, kinetics, nitrone, nitroxide, solvent effect",

author = "Cherkasov, {Sergey A.} and Kaletina, {Polina M.} and Polienko, {Yuliya F.} and Parkhomenko, {Dmitriy A.}",

note = "Funding Information: The work was supported by the Russian Science Foundation (grant No. 20‐73‐00350). The authors acknowledge the Supercomputer Center of Novosibirsk State University for computational resources. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = jul,

doi = "10.1002/cplu.202200119",

language = "English",

volume = "87",

journal = "ChemPlusChem",

issn = "2192-6506",

publisher = "Wiley-VCH Verlag",

number = "7",

}

RIS

TY - JOUR

T1 - The Kinetic Solvent Effect on 1,3-Dipolar Cycloaddition of 2,2,5,5-Tetramethyl-3-imidazoline-3-oxide-1-oxyl

AU - Cherkasov, Sergey A.

AU - Kaletina, Polina M.

AU - Polienko, Yuliya F.

AU - Parkhomenko, Dmitriy A.

N1 - Funding Information: The work was supported by the Russian Science Foundation (grant No. 20‐73‐00350). The authors acknowledge the Supercomputer Center of Novosibirsk State University for computational resources. Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/7

Y1 - 2022/7

N2 - The use of 2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl (1) as a controlling agent in Nitroxide Mediated Polymerization allows for activation of alkoxyamine homolysis by 1,3-dipolar cycloaddition of a vinyl monomer [Edeleva et al. Chem. Commun. 2019, 55, 190–193]. Polymerization can be carried out in a medium with different polarity and hydrogen bonding capacity which affects the rate of 1,3-dipolar cycloaddition reaction. In the present study, the solvent effect on the rate of this reaction was investigated by the electron paramagnetic resonance and density functional theory for the six different dipolarophiles, e. g. styrene, n-butyl acrylate, acrylonitrile, methyl vinyl ketone, maleic anhydride, and N-phenyl maleimide. The rate of 1,3 dipolar cycloaddition of non-polar styrene was found to be slightly dependent on solvent, while one order of magnitude decrease in rate coefficient is observed for other dipolarophiles when going from hexane to methanol.

AB - The use of 2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl (1) as a controlling agent in Nitroxide Mediated Polymerization allows for activation of alkoxyamine homolysis by 1,3-dipolar cycloaddition of a vinyl monomer [Edeleva et al. Chem. Commun. 2019, 55, 190–193]. Polymerization can be carried out in a medium with different polarity and hydrogen bonding capacity which affects the rate of 1,3-dipolar cycloaddition reaction. In the present study, the solvent effect on the rate of this reaction was investigated by the electron paramagnetic resonance and density functional theory for the six different dipolarophiles, e. g. styrene, n-butyl acrylate, acrylonitrile, methyl vinyl ketone, maleic anhydride, and N-phenyl maleimide. The rate of 1,3 dipolar cycloaddition of non-polar styrene was found to be slightly dependent on solvent, while one order of magnitude decrease in rate coefficient is observed for other dipolarophiles when going from hexane to methanol.

KW - 1,3-dipolar cycloaddition

KW - kinetics

KW - nitrone

KW - nitroxide

KW - solvent effect

UR - http://www.scopus.com/inward/record.url?scp=85134556248&partnerID=8YFLogxK

U2 - 10.1002/cplu.202200119

DO - 10.1002/cplu.202200119

M3 - Article

C2 - 35852175

AN - SCOPUS:85134556248

VL - 87

JO - ChemPlusChem

JF - ChemPlusChem

SN - 2192-6506

IS - 7

M1 - e202200119

ER -

ID: 36716356