Half-wave reduction potentials of a set of twelve (E)-4-aryl-4-oxo-2-butenoic acids obtained by direct current polarography in methanol are reported. E1/2 is correlated with Hammett sigma values as well as with values of frontier molecular orbitals calculated at a semiempirical molecular orbital level. Constant potential electrolysis of a representative compound shows that the first polarographic wave corresponds to one-electron reduction. The isolation of the product proves reduction of the activated double bond.
Keywords:
Aroylacrylic acids / Frontier orbitals / Half-wave potentials / Hammett sigma / Linear free energy relationship
TY - JOUR
AU - Pastor, Ferenc T.
AU - Drakulić, Branko
PY - 2010
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/5854
AB - Half-wave reduction potentials of a set of twelve (E)-4-aryl-4-oxo-2-butenoic acids obtained by direct current polarography in methanol are reported. E1/2 is correlated with Hammett sigma values as well as with values of frontier molecular orbitals calculated at a semiempirical molecular orbital level. Constant potential electrolysis of a representative compound shows that the first polarographic wave corresponds to one-electron reduction. The isolation of the product proves reduction of the activated double bond.
PB - Elsevier
T2 - Tetrahedron Letters
T1 - Linear free energy relationships of half-wave reduction potentials of (E)-4-aryl-4-oxo-2-butenoic acids
VL - 51
IS - 4
SP - 734
EP - 738
DO - 10.1016/j.tetlet.2009.11.129
ER -
@article{
author = "Pastor, Ferenc T. and Drakulić, Branko",
year = "2010",
abstract = "Half-wave reduction potentials of a set of twelve (E)-4-aryl-4-oxo-2-butenoic acids obtained by direct current polarography in methanol are reported. E1/2 is correlated with Hammett sigma values as well as with values of frontier molecular orbitals calculated at a semiempirical molecular orbital level. Constant potential electrolysis of a representative compound shows that the first polarographic wave corresponds to one-electron reduction. The isolation of the product proves reduction of the activated double bond.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "Linear free energy relationships of half-wave reduction potentials of (E)-4-aryl-4-oxo-2-butenoic acids",
volume = "51",
number = "4",
pages = "734-738",
doi = "10.1016/j.tetlet.2009.11.129"
}
Pastor, F. T.,& Drakulić, B.. (2010). Linear free energy relationships of half-wave reduction potentials of (E)-4-aryl-4-oxo-2-butenoic acids. in Tetrahedron Letters
Elsevier., 51(4), 734-738.
https://doi.org/10.1016/j.tetlet.2009.11.129
Pastor FT, Drakulić B. Linear free energy relationships of half-wave reduction potentials of (E)-4-aryl-4-oxo-2-butenoic acids. in Tetrahedron Letters. 2010;51(4):734-738.
doi:10.1016/j.tetlet.2009.11.129 .
Pastor, Ferenc T., Drakulić, Branko, "Linear free energy relationships of half-wave reduction potentials of (E)-4-aryl-4-oxo-2-butenoic acids" in Tetrahedron Letters, 51, no. 4 (2010):734-738,
https://doi.org/10.1016/j.tetlet.2009.11.129 . .
