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
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
α,β-epoxy acids / pKa-values / LFER / transmission coefficients / synthesis of trans-β-aroylepoxyacrylic acidsIzvor:
Journal of the Serbian Chemical Society, 2000, 65, 11, 781-788Izdavač:
- Srpsko hemijsko društvo, Beograd
DOI: 10.2298/JSC0011781P
ISSN: 0352-5139
WoS: 000165453400004
Scopus: 2-s2.0-0034361909
URI
http://farfar.pharmacy.bg.ac.rs/handle/123456789/269https://cer.ihtm.bg.ac.rs/handle/123456789/3511
Institucija/grupa
IHTMTY - 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 . .