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Title: Mechanistic investigation of the base-promoted cycloselenoetherification of pent-4-en-1-ol
Authors: Kostic, Marina
Divac, Vera
Puchta, Ralph
Bugarčić Z.
Journal: Journal of Molecular Modeling
Issue Date: 1-Jun-2011
Abstract: The mechanism of phenylselenoetherification of pent-4-en-1-ol using some bases (pyridine, triethylamine, quinoline, 2,2′-bipyridine) as catalyst was examined through studies of kinetics of the cyclization, by UV-VIS spectrophotometry. It was demonstrated that the intramolecular cyclization is facilitated in the presence of bases caused by the hydrogen bond between base and alkenol's OH-group. The obtained values for rate constants have shown that the reaction with triethylamine is the fastest one. Quantum chemical calculations (MP2(fc)/6-311+G**//B3LYP/6-311+G**) show, that the transition state of the cyclisation is SN2 like. © 2010 Springer-Verlag.
Type: Article
DOI: 10.1007/s00894-010-0824-3
ISSN: 16102940
SCOPUS: 79958098664
Appears in Collections:Faculty of Science, Kragujevac
Institute for Information Technologies, Kragujevac
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