The pKa values for a series of eight p-substituted trans-2,3-epoxy-4-phenyl butanoic acids (p-substituted trans-β-aroylepoxyacrylic acids) have been determined potentiometrically in aqueous media at 25 °C at an ionic strength of 0.1 mol/dm3 (NaCl). The transmission of polar effects from the substituents on the phenyl nucleus to the carboxylic group through the side chain involving a carbonyl group and an epoxide ring was investigated. The pKa values were correlated with structure using the Hammett, Taft and Yukawa-Tsuno approaches. The Hammett ρ constant (0.34) was compared with analogue values for structurally similar acids.
Određene su pKa vrednosti za seriju od osam p-supstituisanih trans-2,3-epoksi-4-okso-4-fenilbutanskih kiselina (p-supstituisanih trans-β-aroilepoksiakrilnih kiselina). Vrednosti su određene potenciometrijski u vodenoj sredini na 25 °C i jonskoj sili 0.1 mol/dm3 (NaCl). Proučavan je prenos polarnih efekata sa supstituenata na fenil jezgru ka karboksilnoj grupi kroz bočni niz koji sadrži karbonilnu grupu i epoksidni prsten. pKa vrednosti su korelisane sa strukturom primenom Hammett-ovog, Taft-ovog i Yukawa-Tsuno-ovog pristupa. Hammett-ova ρ konstanta (0,34) je upoređena sa analognim vrednostima za strukturno slične kiseline.
TY - JOUR
AU - Pfendt, Lidija
AU - Popović, Gordana
AU - Kostić, M.
AU - Stevović, Lj.
AU - Drakulić, Branko
AU - Juranić, Ivan
PY - 2000
UR - http://farfar.pharmacy.bg.ac.rs/handle/123456789/269
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3511
AB - The pKa values for a series of eight p-substituted trans-2,3-epoxy-4-phenyl butanoic acids (p-substituted trans-β-aroylepoxyacrylic acids) have been determined potentiometrically in aqueous media at 25 °C at an ionic strength of 0.1 mol/dm3 (NaCl). The transmission of polar effects from the substituents on the phenyl nucleus to the carboxylic group through the side chain involving a carbonyl group and an epoxide ring was investigated. The pKa values were correlated with structure using the Hammett, Taft and Yukawa-Tsuno approaches. The Hammett ρ constant (0.34) was compared with analogue values for structurally similar acids.
AB - Određene su pKa vrednosti za seriju od osam p-supstituisanih trans-2,3-epoksi-4-okso-4-fenilbutanskih kiselina (p-supstituisanih trans-β-aroilepoksiakrilnih kiselina). Vrednosti su određene potenciometrijski u vodenoj sredini na 25 °C i jonskoj sili 0.1 mol/dm3 (NaCl). Proučavan je prenos polarnih efekata sa supstituenata na fenil jezgru ka karboksilnoj grupi kroz bočni niz koji sadrži karbonilnu grupu i epoksidni prsten. pKa vrednosti su korelisane sa strukturom primenom Hammett-ovog, Taft-ovog i Yukawa-Tsuno-ovog pristupa. Hammett-ova ρ konstanta (0,34) je upoređena sa analognim vrednostima za strukturno slične kiseline.
PB - Srpsko hemijsko društvo, Beograd
T2 - Journal of the Serbian Chemical Society
T1 - Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids
T1 - Određivanje pKa vrednosti i korelacija sa strukturom p-supstituisanih trans-2,3-epoksi-4-okso-4-fenilbutanskih kiselina
VL - 65
IS - 11
SP - 781
EP - 788
DO - 10.2298/JSC0011781P
ER -
@article{
author = "Pfendt, Lidija and Popović, Gordana and Kostić, M. and Stevović, Lj. and Drakulić, Branko and Juranić, Ivan",
year = "2000",
abstract = "The pKa values for a series of eight p-substituted trans-2,3-epoxy-4-phenyl butanoic acids (p-substituted trans-β-aroylepoxyacrylic acids) have been determined potentiometrically in aqueous media at 25 °C at an ionic strength of 0.1 mol/dm3 (NaCl). The transmission of polar effects from the substituents on the phenyl nucleus to the carboxylic group through the side chain involving a carbonyl group and an epoxide ring was investigated. The pKa values were correlated with structure using the Hammett, Taft and Yukawa-Tsuno approaches. The Hammett ρ constant (0.34) was compared with analogue values for structurally similar acids., Određene su pKa vrednosti za seriju od osam p-supstituisanih trans-2,3-epoksi-4-okso-4-fenilbutanskih kiselina (p-supstituisanih trans-β-aroilepoksiakrilnih kiselina). Vrednosti su određene potenciometrijski u vodenoj sredini na 25 °C i jonskoj sili 0.1 mol/dm3 (NaCl). Proučavan je prenos polarnih efekata sa supstituenata na fenil jezgru ka karboksilnoj grupi kroz bočni niz koji sadrži karbonilnu grupu i epoksidni prsten. pKa vrednosti su korelisane sa strukturom primenom Hammett-ovog, Taft-ovog i Yukawa-Tsuno-ovog pristupa. Hammett-ova ρ konstanta (0,34) je upoređena sa analognim vrednostima za strukturno slične kiseline.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids, Određivanje pKa vrednosti i korelacija sa strukturom p-supstituisanih trans-2,3-epoksi-4-okso-4-fenilbutanskih kiselina",
volume = "65",
number = "11",
pages = "781-788",
doi = "10.2298/JSC0011781P"
}
Pfendt, L., Popović, G., Kostić, M., Stevović, Lj., Drakulić, B.,& Juranić, I.. (2000). Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 65(11), 781-788.
https://doi.org/10.2298/JSC0011781P
Pfendt L, Popović G, Kostić M, Stevović L, Drakulić B, Juranić I. Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids. in Journal of the Serbian Chemical Society. 2000;65(11):781-788.
doi:10.2298/JSC0011781P .
Pfendt, Lidija, Popović, Gordana, Kostić, M., Stevović, Lj., Drakulić, Branko, Juranić, Ivan, "Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids" in Journal of the Serbian Chemical Society, 65, no. 11 (2000):781-788,
https://doi.org/10.2298/JSC0011781P . .
