TY  - JOUR
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Juranić, Ivan
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1135
AB  - The extensive computation study was done to elucidate the mechanism of formation dibromoepoxide from cyclohexanone and bromoform. In this reaction, the formation of dihaloepoxide 2 is postulated as a key step that determines the distribution and stereochemistry of products. Two mechanistic paths of reaction were investigated: the addition of dibromocarbene to carbonyl group of ketone, and the addition of tribromomethyl carbanion to the same (C=O) group. The mechanisms for the addition reactions of dibromocarbenes and tribromomethyl carbanions with cyclohexanone have been investigated using ab initio HF/6-311++G** and MP2/6-311+G* level of theory. Solvent effects on these reactions have been explored by calculations which included a continuum polarizable conductor model (CPCM) for the solvent (H2O). The calculations showed that both mechanisms are possible and are exothermic, but have markedly different activation energies.
PB  - Springer, New York
T2  - Journal of Molecular Modeling
T1  - Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform
VL  - 18
IS  - 10
SP  - 4721
EP  - 4728
DO  - 10.1007/s00894-012-1468-2
ER  - 

@article{
author = "Vitnik, Vesna and Vitnik, Željko and Juranić, Ivan",
year = "2012",
abstract = "The extensive computation study was done to elucidate the mechanism of formation dibromoepoxide from cyclohexanone and bromoform. In this reaction, the formation of dihaloepoxide 2 is postulated as a key step that determines the distribution and stereochemistry of products. Two mechanistic paths of reaction were investigated: the addition of dibromocarbene to carbonyl group of ketone, and the addition of tribromomethyl carbanion to the same (C=O) group. The mechanisms for the addition reactions of dibromocarbenes and tribromomethyl carbanions with cyclohexanone have been investigated using ab initio HF/6-311++G** and MP2/6-311+G* level of theory. Solvent effects on these reactions have been explored by calculations which included a continuum polarizable conductor model (CPCM) for the solvent (H2O). The calculations showed that both mechanisms are possible and are exothermic, but have markedly different activation energies.",
publisher = "Springer, New York",
journal = "Journal of Molecular Modeling",
title = "Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform",
volume = "18",
number = "10",
pages = "4721-4728",
doi = "10.1007/s00894-012-1468-2"
}

Vitnik, V., Vitnik, Ž.,& Juranić, I.. (2012). Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform. in Journal of Molecular Modeling
Springer, New York., 18(10), 4721-4728.
https://doi.org/10.1007/s00894-012-1468-2

Vitnik V, Vitnik Ž, Juranić I. Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform. in Journal of Molecular Modeling. 2012;18(10):4721-4728.
doi:10.1007/s00894-012-1468-2 .

Vitnik, Vesna, Vitnik, Željko, Juranić, Ivan, "Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform" in Journal of Molecular Modeling, 18, no. 10 (2012):4721-4728,
https://doi.org/10.1007/s00894-012-1468-2 . .