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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

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0352-51390011781P.pdf (4.449Mb)
Authors
Pfendt, Lidija
Popović, Gordana
Kostić, M.
Stevović, Lj.
Drakulić, Branko
Juranić, Ivan
Article (Published version)
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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.
Keywords:
α,β-epoxy acids / pKa-values / LFER / transmission coefficients / synthesis of trans-β-aroylepoxyacrylic acids
Source:
Journal of the Serbian Chemical Society, 2000, 65, 11, 781-788
Publisher:
  • Srpsko hemijsko društvo, Beograd

DOI: 10.2298/JSC0011781P

ISSN: 0352-5139

WoS: 000165453400004

Scopus: 2-s2.0-0034361909
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URI
http://farfar.pharmacy.bg.ac.rs/handle/123456789/269
http://cer.ihtm.bg.ac.rs/handle/123456789/3511
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