Please use this identifier to cite or link to this item: https://scidar.kg.ac.rs/handle/123456789/12483
Title: Mechanistic insight into alkylation of the ethyl acetoacetate anion with different ethyl halides
Authors: Markovic, Svetlana
Đurđević Nikolić, Jelena
Vukosavljevic M.
Petrović, Zorica
Journal: Russian Journal of Physical Chemistry A
Issue Date: 1-Dec-2013
Abstract: The alkylation reactions of the ambident ethyl acetoacetate anion with C2H5X (X = F, Cl, Br, and I) in the O2, C3, and O4 positions of the anion were investigated at the B3LYP/6-311+G(d,p) level of theory. It was found that the ethylation reaction does not occur in the position O4, as well as with ethyl fluoride in any position of the anion, due to very high activation energies and thermodynamic instability of the hypothetic products. The activation energies for the reactions in the position O2 are lower in comparison to the position C3, but the products of the reactions in the C3 position are more stable than those in the position O4, implying that the C/O products ratio is controlled by both thermodynamic and kinetic factors, leading to the O2-product with the chloride, and C3-product with the iodide as leaving group. © 2013 Pleiades Publishing, Ltd.
URI: https://scidar.kg.ac.rs/handle/123456789/12483
Type: article
DOI: 10.1134/S0036024413130165
ISSN: 00360244
SCOPUS: 84888142374
Appears in Collections:Faculty of Science, Kragujevac

Page views(s)

58

Downloads(s)

1

Files in This Item:
File Description SizeFormat 
PaperMissing.pdf
  Restricted Access
29.86 kBAdobe PDFThumbnail
View/Open


Items in SCIDAR are protected by copyright, with all rights reserved, unless otherwise indicated.