Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 2006, 71, 107-128
https://doi.org/10.1135/cccc20060107

Kinetic Study of Hydrolysis of Benzoates. Part XXV. Ortho Substituent Effect in Alkaline Hydrolysis of Phenyl Esters of Substituted Benzoic Acids in Water

Vilve Nummert, Mare Piirsalu*, Vahur Mäemets and Ilmar Koppel

Institute of Chemical Physics, Tartu University, Jakobi 2, 51014 Tartu, Estonia

Crossref Cited-by Linking

  • Pyun Sang Yong, Paik Kyu Cheol, Han Man So, Hong Seung Taek, Cho Bong Rae: Reactions of 2,4‐dinitrophenyl 5‐substituted‐2‐thiophenecarboxylate promoted by 4‐ZC6H4O−/4‐ZC6H4OH in 20 mol% DMSO(aq). Effects of leaving group and nucleophile on the acyl transfer reactions. Bulletin Korean Chem Soc 2023, 44, 952. <https://doi.org/10.1002/bkcs.12780>
  • Pyun Sang Yong, Paik Kyu Cheol, Han Man So, Cho Bong Rae: Reactions of 4‐Nitrophenyl 5‐substituted Furan‐2‐carboxylates with R2NH/R2NH2+ in 20 mol% DMSO(aq): Effect of Aryl Group on the Acyl‐Transfer Reaction. Bulletin Korean Chem Soc 2021, 42, 994. <https://doi.org/10.1002/bkcs.12296>
  • Pyun Sang Yong, Paik Kyu Cheol, Han Man So, Cho Bong Rae: Reactions of 2,4‐Dinitrophenyl 5‐substituted‐2‐thiophenecarboxylates with R2NH/R2NH2+ in 20 Mol % DMSO(aq). Effects of 5‐Thienyl Substituent and Leaving Group on the Reaction Mechanism. Bulletin Korean Chem Soc 2019, 40, 983. <https://doi.org/10.1002/bkcs.11857>
  • Nummert Vilve, Piirsalu Mare, Toom Lauri, Kesvatera Tõnu, Leito Ivo, Koppel Ilmar A.: Effect of charged and ortho substituents on 17O NMR chemical shifts of substituted phenyl tosylates in DMSO. J of Physical Organic Chem 2018, 31. <https://doi.org/10.1002/poc.3870>
  • Shin Young‐Hee, Koh Han‐Joong, Um Ik‐Hwan: Kinetic Study on Alkaline Hydrolysis of 2‐Pyridyl and 4‐Pyridyl X‐substituted‐Benzoates: Effects of Benzoyl Substituent X and Leaving‐Group Basicity on Reactivity and Reaction Mechanism. Bulletin Korean Chem Soc 2017, 38, 1138. <https://doi.org/10.1002/bkcs.11233>
  • Nummert Vilve, Piirsalu Mare, Vahur Signe, Toom Lauri, Leito Ivo, Koppel Ilmar A.: Effects of neutral and charged substituents on the infrared carbonyl stretching frequencies in phenyl and alkyl benzoates in DMSO. J. Phys. Org. Chem. 2017, 30, e3608. <https://doi.org/10.1002/poc.3608>
  • Shin Young‐Hee, Kang Ji‐Sun, Um Ik‐Hwan: Alkaline Hydrolysis of 4‐Nitrophenyl X‐Substituted‐Benzoates Revisited: New Insights from Yukawa–Tsuno Equation. Bulletin Korean Chem Soc 2016, 37, 2062. <https://doi.org/10.1002/bkcs.11000>
  • Nummert Vilve, Piirsalu Mare, Koppel Ilmar A.: Prediction of ortho substituent effect in alkaline hydrolysis of substituted phenyl benzoates in aqueous acetonitrile. J. Phys. Org. Chem. 2013, 26, 352. <https://doi.org/10.1002/poc.3096>
  • Nummert Vilve, Piirsalu Mare, Koppel Ilmar A.: Prediction of ortho substituent effect in alkaline hydrolysis of phenyl esters of substituted benzoic acids in aqueous acetonitrile. cent.eur.j.chem. 2013, 11, 1964. <https://doi.org/10.2478/s11532-013-0321-5>
  • Nummert Vilve, Mäemets Vahur, Piirsalu Mare, Koppel Ilmar A.: Influence of ortho substituents on 17O NMR chemical shifts in phenyl esters of substituted benzoic acids. J of Physical Organic Chem 2011, 24, 539. <https://doi.org/10.1002/poc.1784>
  • Sen Gupta Susanta K., Mishra Sangeeta: Kinetics of Proton Transfer between Ortho Substituted Benzoic Acids and the Carbinol Base of Crystal Violet in Toluene. Ortho Effect on the Reactivity of Benzoic Acids in Apolar Aprotic Solvents. J. Phys. Chem. A 2011, 115, 4616. <https://doi.org/10.1021/jp110851s>
  • Nummert Vilve, Mäemets Vahur, Piirsalu Mare, Vahur Signe, Koppel Ilmar A.: 17O NMR study of ortho and alkyl substituent effects in substituted phenyl and alkyl esters of benzoic acids. Collect. Czech. Chem. Commun. 2011, 76, 1737. <https://doi.org/10.1135/cccc2011100>
  • Nummert Vilve, Piirsalu Mare, Koppel Ilmar A.: Influence of solvent on the ortho substituent effect in the alkaline hydrolysis of phenyl esters of substituted benzoic acids. J of Physical Organic Chem 2010, 23, 497. <https://doi.org/10.1002/poc.1628>
  • Nummert Vilve, Piirsalu Mare, Mäemets Vahur, Vahur Signe, Koppel Ilmar A.: Effect of ortho substituents on carbonyl carbon 13C NMR chemical shifts in substituted phenyl benzoates. J of Physical Organic Chem 2009, 22, 1155. <https://doi.org/10.1002/poc.1569>
  • Nummert Vilve, Piirsalu Mare, Vahur Signe, Travnikova Oksana, Koppel Ilmar A.: Kinetic study of hydrolysis of benzoates. part xxvii. ortho substituent effect in alkaline hydrolysis of phenyl esters of substituted benzoic acids in aqueous Bu4NBr. Collect. Czech. Chem. Commun. 2009, 74, 29. <https://doi.org/10.1135/cccc2008019>
  • Nummert Vilve, Travnikova Oksana, Vahur Signe, Leito Ivo, Piirsalu Mare, Mäemets Vahur, Koppel Ivar, Koppel Ilmar A.: Influence of substituents on the infrared stretching frequencies of carbonyl group in esters of benzoic acid. J of Physical Organic Chem 2006, 19, 654. <https://doi.org/10.1002/poc.1112>
  • Exner Otto, Böhm Stanislav: Analysis of the Ortho Effect: Basicity of 2-Substituted Benzonitriles. Collect. Czech. Chem. Commun. 2006, 71, 1239. <https://doi.org/10.1135/cccc20061239>