Determination and structural correlation of the pKa values of p-substituted trans-2,3-epoxy-4-oxo-4-phenylbutanoic acids
| Autor: | Lj. Stevovic, Ivan O. Juranić, M. Kostic, Gordana Popović, Branko J. Drakulić, Lidija B. Pfendt |
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| Rok vydání: | 2000 |
| Předmět: |
LFER
transmission coefficients 02 engineering and technology synthesis of trans-b-aroylepoxyacrylic acids 010402 general chemistry 01 natural sciences Medicinal chemistry lcsh:Chemistry Structural correlation A value Chemistry General Chemistry Epoxy pKa-values 021001 nanoscience & nanotechnology α β-epoxy acids b-epoxy acids 0104 chemical sciences lcsh:QD1-999 lfer pka-values visual_art visual_art.visual_art_medium 0210 nano-technology synthesis of trans-β-aroylepoxyacrylic acids |
| Zdroj: | Journal of the Serbian Chemical Society Scopus-Elsevier Journal of the Serbian Chemical Society, Vol 65, Iss 11, Pp 781-788 (2000) |
| ISSN: | 1820-7421 0352-5139 |
| DOI: | 10.2298/jsc0011781p |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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