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Tetrabromomethane as an Organic Catalyst : a Kinetic Study of CBr₄-Catalyzed Schiff Condensation. / Yunusova, Sevilya N.; Bolotin, Dmitrii S.; Vovk, Mikhail A.; Tolstoy, Peter M.; Kukushkin, Vadim Yu.

In: European Journal of Organic Chemistry, Vol. 2020, No. 43, 22.11.2020, p. 6763-6769.

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

BibTeX

@article{78535396e79b44bd99d748d55447f0a4,

title = "Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr4-Catalyzed Schiff Condensation",

abstract = "Tetrabromomethane functions as an organic catalyst for non-redox reactions of carbonyl species and, in particular, it enhances the aldehyde–acyl hydrazide condensation to give N-acyl hydrazones. This simple, inexpensive, and commercially available halomethane provides up to 14-fold acceleration of the Schiff reaction; the kinetic data indicate that the studied condensation exhibits the first order on CBr4. The catalytic activity of CBr4 is significantly higher than the activity of other halogen-containing species, such as CHX3 or ArX (X = Cl, Br, I).",

keywords = "Acyl hydrazides, Aldehydes, Haloalkanes, Homogeneous catalysis, Schiff bases, BRONSTED ACID, SUBSTITUTION, ACTIVATION, CARBOXYLIC ESTERS, NONCOVALENT INTERACTIONS, HALOGEN, SQUARAMIDES, HYDROGEN-BONDING ORGANOCATALYSTS, ASYMMETRIC ORGANOCATALYSIS, CBR4",

author = "Yunusova, {Sevilya N.} and Bolotin, {Dmitrii S.} and Vovk, {Mikhail A.} and Tolstoy, {Peter M.} and Kukushkin, {Vadim Yu}",

note = "Funding Information: The kinetic part of this work was supported by the Russian Science Foundation (grant 20‐73‐10013), whereas the synthetic part was provided by the Russian Foundation for Basic Research (grant 19‐03‐00044). Physicochemical studies were performed at the Center for Magnetic Resonance, Center for X‐ray Diffraction Studies, Chemistry Educational Centre, and Center for Chemical Analysis and Materials Research (all belonging to Saint Petersburg State University). V. Y. K. is grateful to South Ural State University (Act 211 Government of the Russian Federation, contract No 02.A03.21.0011) for putting facilities at his disposal. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2020",

month = nov,

day = "22",

doi = "10.1002/ejoc.202001180",

language = "English",

volume = "2020",

pages = "6763--6769",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-Blackwell",

number = "43",

}

RIS

TY - JOUR

T1 - Tetrabromomethane as an Organic Catalyst

T2 - a Kinetic Study of CBr4-Catalyzed Schiff Condensation

AU - Yunusova, Sevilya N.

AU - Bolotin, Dmitrii S.

AU - Vovk, Mikhail A.

AU - Tolstoy, Peter M.

AU - Kukushkin, Vadim Yu

N1 - Funding Information: The kinetic part of this work was supported by the Russian Science Foundation (grant 20‐73‐10013), whereas the synthetic part was provided by the Russian Foundation for Basic Research (grant 19‐03‐00044). Physicochemical studies were performed at the Center for Magnetic Resonance, Center for X‐ray Diffraction Studies, Chemistry Educational Centre, and Center for Chemical Analysis and Materials Research (all belonging to Saint Petersburg State University). V. Y. K. is grateful to South Ural State University (Act 211 Government of the Russian Federation, contract No 02.A03.21.0011) for putting facilities at his disposal. Publisher Copyright: © 2020 Wiley-VCH GmbH Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/11/22

Y1 - 2020/11/22

N2 - Tetrabromomethane functions as an organic catalyst for non-redox reactions of carbonyl species and, in particular, it enhances the aldehyde–acyl hydrazide condensation to give N-acyl hydrazones. This simple, inexpensive, and commercially available halomethane provides up to 14-fold acceleration of the Schiff reaction; the kinetic data indicate that the studied condensation exhibits the first order on CBr4. The catalytic activity of CBr4 is significantly higher than the activity of other halogen-containing species, such as CHX3 or ArX (X = Cl, Br, I).

AB - Tetrabromomethane functions as an organic catalyst for non-redox reactions of carbonyl species and, in particular, it enhances the aldehyde–acyl hydrazide condensation to give N-acyl hydrazones. This simple, inexpensive, and commercially available halomethane provides up to 14-fold acceleration of the Schiff reaction; the kinetic data indicate that the studied condensation exhibits the first order on CBr4. The catalytic activity of CBr4 is significantly higher than the activity of other halogen-containing species, such as CHX3 or ArX (X = Cl, Br, I).

KW - Acyl hydrazides

KW - Aldehydes

KW - Haloalkanes

KW - Homogeneous catalysis

KW - Schiff bases

KW - BRONSTED ACID

KW - SUBSTITUTION

KW - ACTIVATION

KW - CARBOXYLIC ESTERS

KW - NONCOVALENT INTERACTIONS

KW - HALOGEN

KW - SQUARAMIDES

KW - HYDROGEN-BONDING ORGANOCATALYSTS

KW - ASYMMETRIC ORGANOCATALYSIS

KW - CBR4

UR - http://www.scopus.com/inward/record.url?scp=85093680142&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/163bbb6e-3182-337f-b0bc-d311d2baf75d/

U2 - 10.1002/ejoc.202001180

DO - 10.1002/ejoc.202001180

M3 - Article

AN - SCOPUS:85093680142

VL - 2020

SP - 6763

EP - 6769

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 43

ER -

ID: 70758143

Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr4-Catalyzed Schiff Condensation

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Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr₄-Catalyzed Schiff Condensation