Mechanism(s) of thermal decomposition of N-Nitrosoamides: A density functional theory study

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Mechanism(s) of thermal decomposition of N-Nitrosoamides : A density functional theory study. / Brea, Oriana; Daver, Henrik; Rebek, Julius; Himo, Fahmi.

In: Tetrahedron, Vol. 75, No. 8, 22.02.2019, p. 929-935.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Brea, O, Daver, H, Rebek, J & Himo, F 2019, 'Mechanism(s) of thermal decomposition of N-Nitrosoamides: A density functional theory study', Tetrahedron, vol. 75, no. 8, pp. 929-935. https://doi.org/10.1016/j.tet.2018.12.054

APA

Brea, O., Daver, H., Rebek, J., & Himo, F. (2019). Mechanism(s) of thermal decomposition of N-Nitrosoamides: A density functional theory study. Tetrahedron, 75(8), 929-935. https://doi.org/10.1016/j.tet.2018.12.054

Vancouver

Brea O, Daver H, Rebek J, Himo F. Mechanism(s) of thermal decomposition of N-Nitrosoamides: A density functional theory study. Tetrahedron. 2019 Feb 22;75(8):929-935. https://doi.org/10.1016/j.tet.2018.12.054

Author

Brea, Oriana ; Daver, Henrik ; Rebek, Julius ; Himo, Fahmi. / Mechanism(s) of thermal decomposition of N-Nitrosoamides : A density functional theory study. In: Tetrahedron. 2019 ; Vol. 75, No. 8. pp. 929-935.

Bibtex

@article{032d9f2f1d614f30a1a30e84a1428339,
title = "Mechanism(s) of thermal decomposition of N-Nitrosoamides: A density functional theory study",
abstract = "The thermal decomposition of N-nitrosoamides has experimentally been demonstrated to depend on several factors, such as temperature, solvent and the substituents on the substrate. Consequently, a number of reaction mechanisms have been proposed for this process in the literature. In this work, we present a comprehensive computational investigation in which we examine the detailed reaction mechanisms for two N-nitrosoamides (with aliphatic and aromatic substituents) in two different solvents (mesitylene and methanol). It is shown that the reaction mechanism can change dramatically with the nature of the substrate and the choice of solvent. Importantly, it is found that the polar solvent stabilizes ion-pairs that are unstable in the non-polar solvent, which can play a key role in the mechanism.",
keywords = "Computational chemistry, Density functional theory, Nitrosoamides, Reaction mechanism, Transition state",
author = "Oriana Brea and Henrik Daver and Julius Rebek and Fahmi Himo",
year = "2019",
month = feb,
day = "22",
doi = "10.1016/j.tet.2018.12.054",
language = "English",
volume = "75",
pages = "929--935",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Pergamon Press",
number = "8",

}

RIS

TY - JOUR

T1 - Mechanism(s) of thermal decomposition of N-Nitrosoamides

T2 - A density functional theory study

AU - Brea, Oriana

AU - Daver, Henrik

AU - Rebek, Julius

AU - Himo, Fahmi

PY - 2019/2/22

Y1 - 2019/2/22

N2 - The thermal decomposition of N-nitrosoamides has experimentally been demonstrated to depend on several factors, such as temperature, solvent and the substituents on the substrate. Consequently, a number of reaction mechanisms have been proposed for this process in the literature. In this work, we present a comprehensive computational investigation in which we examine the detailed reaction mechanisms for two N-nitrosoamides (with aliphatic and aromatic substituents) in two different solvents (mesitylene and methanol). It is shown that the reaction mechanism can change dramatically with the nature of the substrate and the choice of solvent. Importantly, it is found that the polar solvent stabilizes ion-pairs that are unstable in the non-polar solvent, which can play a key role in the mechanism.

AB - The thermal decomposition of N-nitrosoamides has experimentally been demonstrated to depend on several factors, such as temperature, solvent and the substituents on the substrate. Consequently, a number of reaction mechanisms have been proposed for this process in the literature. In this work, we present a comprehensive computational investigation in which we examine the detailed reaction mechanisms for two N-nitrosoamides (with aliphatic and aromatic substituents) in two different solvents (mesitylene and methanol). It is shown that the reaction mechanism can change dramatically with the nature of the substrate and the choice of solvent. Importantly, it is found that the polar solvent stabilizes ion-pairs that are unstable in the non-polar solvent, which can play a key role in the mechanism.

KW - Computational chemistry

KW - Density functional theory

KW - Nitrosoamides

KW - Reaction mechanism

KW - Transition state

UR - http://www.scopus.com/inward/record.url?scp=85060083379&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2018.12.054

DO - 10.1016/j.tet.2018.12.054

M3 - Journal article

AN - SCOPUS:85060083379

VL - 75

SP - 929

EP - 935

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 8

ER -

ID: 241045162