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Pure Appl. Chem., 2009, Vol. 81, No. 4, pp. 685-696

http://dx.doi.org/10.1351/PAC-CON-08-08-11

Kinetics and mechanism of the aminolysis of thioesters and thiocarbonates in solution

Enrique A. Castro

Faculty of Chemistry, Pontifical Catholic University of Chile, Casilla 306, Santiago 6094411, Chile

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  • Um Ik-Hwan, Bae Ae-Ri, Um Tae-Il: Comparison of Aminolysis of 2-Pyridyl and 4-Pyridyl X-Substituted Benzoates in Acetonitrile: Evidence for a Concerted Mechanism Involving a Cyclic Transition State. J. Org. Chem. 2014, 79, 1206. <http://dx.doi.org/10.1021/jo402629e>
  • Dorff Giselher, Hahn Mathias, Laschewsky André, Lieske Antje: Optimization of the property profile of poly-L -lactide by synthesis of PLLA-polystyrene-block copolymers. J. Appl. Polym. Sci. 2013, 127, 120. <http://dx.doi.org/10.1002/app.37836>
  • Monbaliu Jean-Christophe M., Dive Georges, Stevens Christian V., Katritzky Alan R.: Governing Parameters of Long-Range Intramolecular S-to-N Acyl Transfers within (S)-Acyl Isopeptides. J. Chem. Theory Comput. 2013, 9, 927. <http://dx.doi.org/10.1021/ct300830k>
  • Um Ik-Hwan, Kang Ji-Sun, Park Jong-Yoon: Kinetic Study on Michael-Type Reactions of β-Nitrostyrenes with Cyclic Secondary Amines in Acetonitrile: Transition-State Structures and Reaction Mechanism Deduced from Negative Enthalpy of Activation and Analyses of LFERs. J. Org. Chem. 2013, 78, 5604. <http://dx.doi.org/10.1021/jo4007442>
  • Lee Ji-Youn, Kim Mi-Yeon, Um Ik-Hwan: Kinetic Study on Nucleophilic Displacement Reactions of Y-Substituted-Phenyl 2-Methylbenzoates with Cyclic Secondary Amines in Acetonitrile: Effects of Modification of 2-MeO in Benzoyl Moiety by 2-Me on Reactivity and Reaction Mechanism. Bulletin of the Korean Chemical Society 2013, 34, 3795. <http://dx.doi.org/10.5012/bkcs.2013.34.12.3795>
  • Kim Min-Young, Lee Jae-In, Um Ik-Hwan: Aminolysis of Benzyl 2-Pyridyl Thionocarbonate and t-Butyl 2-Pyridyl Thionocarbonate: Effects of Nonleaving Groups on Reactivity and Reaction Mechanism. Bulletin of the Korean Chemical Society 2013, 34, 1115. <http://dx.doi.org/10.5012/bkcs.2013.34.4.1115>
  • Song Yoon-Ju, Kim Min-Young, Um Ik-Hwan: A Kinetic Study on Ethylaminolysis of Phenyl Y-Substituted-Phenyl Carbonates: Effect of Leaving-Group Substituents on Reactivity and Reaction Mechanism. Bulletin of the Korean Chemical Society 2013, 34, 1722. <http://dx.doi.org/10.5012/bkcs.2013.34.6.1722>
  • Kang Ji-Sun, Song Yoon-Ju, Um Ik-Hwan: Leaving-Group Substituent Controls Reactivity and Reaction Mechanism in Aminolysis of Phenyl Y-Substituted-Phenyl Carbonates. Bulletin of the Korean Chemical Society 2013, 34, 2023. <http://dx.doi.org/10.5012/bkcs.2013.34.7.2023>
  • Kim Min-Young, Bae Ae Ri, Um Ik-Hwan: A Kinetic Study on Aminolysis of Benzyl 2-Pyridyl Thionocarbonate and t-Butyl 2-Pyridyl Thionocarbonate: Effects of Polarizability and Steric Hindrance on Reactivity and Reaction Mechanism. Bulletin of the Korean Chemical Society 2013, 34, 2325. <http://dx.doi.org/10.5012/bkcs.2013.34.8.2325>
  • Son Yu-Jin, Kim Eun-Hee, Kang Ji-Sun, Um Ik-Hwan: Structure-Reactivity Correlations in Nucleophilic Displacement Reactions of Y-Substituted-Phenyl X-Substituted-Cinnamates with Z-Substituted-Phenoxides. Bulletin of the Korean Chemical Society 2013, 34, 2455. <http://dx.doi.org/10.5012/bkcs.2013.34.8.2455>
  • Um Ik-Hwan, Bae Ae Ri: Electronic Nature of Substituent X Governs Reaction Mechanism in Aminolysis of 4-Pyridyl X-Substituted-Benzoates in Acetonitrile. J. Org. Chem. 2012, 77, 5781. <http://dx.doi.org/10.1021/jo300961y>
  • Nigst Tobias A., Antipova Anna, Mayr Herbert: Nucleophilic Reactivities of Hydrazines and Amines: The Futile Search for the α-Effect in Hydrazine Reactivities. J. Org. Chem. 2012, 77, 8142. <http://dx.doi.org/10.1021/jo301497g>
  • Um Ik-Hwan, Im Li-Ra, Kang Ji-Sun, Bursey Samantha S., Dust Julian M.: Mechanistic Assessment of SNAr Displacement of Halides from 1-Halo-2,4-dinitrobenzenes by Selected Primary and Secondary Amines: Brønsted and Mayr Analyses. J. Org. Chem. 2012, 77, 9738. <http://dx.doi.org/10.1021/jo301862b>
  • Monbaliu Jean-Christophe M., Katritzky Alan R.: Recent trends in Cys- and Ser/Thr-based synthetic strategies for the elaboration of peptide constructs. Chem. Commun. 2012, 48, 11601. <http://dx.doi.org/10.1039/c2cc34434c>
  • Min Se-Won, Kim Min-Young, Um Ik-Hwan: A Kinetic Study on Nucleophilic Substitution Reactions of Phenyl Y-Substituted-Phenyl Carbonates with Z-Substituted-Phenoxides: Effect of Modification of Nonleaving Group from Benzoyl to Phenyloxycarbonyl on Reactivity and Reaction Mechanism. Bulletin of the Korean Chemical Society 2012, 33, 3253. <http://dx.doi.org/10.5012/bkcs.2012.33.10.3253>
  • Um Ik-Hwan, Kang Ji-Sun, Kim Chae-Won, Lee Jae-In: Alkali-Metal Ion Catalysis in Alkaline Ethanolysis of 2-Pyridyl Benzoate and Benzyl 2-Pyridyl Carbonate: Effect of Modification of Nonleaving Group from Benzoyl to Benzyloxycarbonyl. Bull Kor Chem Soc 2012, 33, 519. <http://dx.doi.org/10.5012/bkcs.2012.33.2.519>
  • Bae Ae-Ri, Um Ik-Hwan: Kinetics and Reaction Mechanism of Aminolyses of Benzyl 2-Pyridyl Carbonate and t-Butyl 2-Pyridyl Carbonate in Acetonitrile. Bulletin of the Korean Chemical Society 2012, 33, 1547. <http://dx.doi.org/10.5012/bkcs.2012.33.5.1547>
  • Kang Ji-Sun, Lee Jae-In, Um Ik-Hwan: Kinetics and Reaction Mechanism of Aminolyses of Benzyl 2-Pyridyl Carbonate and t-Butyl 2-Pyridyl Carbonate: Effect of Nonleaving Group on Reactivity and Reaction Mechanism. Bulletin of the Korean Chemical Society 2012, 33, 1551. <http://dx.doi.org/10.5012/bkcs.2012.33.5.1551>
  • Kang Ji-Sun, Um Ik-Hwan: Kinetics and Reaction Mechanism for Aminolysis of Benzyl 4-Pyridyl Carbonate in H2O: Effect of Modification of Nucleofuge from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Mechanism. Bulletin of the Korean Chemical Society 2012, 33, 2269. <http://dx.doi.org/10.5012/bkcs.2012.33.7.2269>
  • Bae Ae-Ri, Um Ik-Hwan: Aminolysis of Benzyl 4-Pyridyl Carbonate in Acetonitrile: Effect of Modification of Leaving Group from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Mechanism. Bulletin of the Korean Chemical Society 2012, 33, 2719. <http://dx.doi.org/10.5012/bkcs.2012.33.8.2719>
  • Kang Ji-Sun, Lee Jae-In, Um Ik-Hwan: A Kinetic Study on Aminolysis of t-Butyl 4-Pyridyl Carbonate and Related Compounds: Effect of Leaving and Nonleaving Groups on Reaction Mechanism. Bulletin of the Korean Chemical Society 2012, 33, 2971. <http://dx.doi.org/10.5012/bkcs.2012.33.9.2971>
  • Um Ik-Hwan, Bae Ae Ri: Aminolysis of Y-Substituted-phenyl 2-Methoxybenzoates in Acetonitrile: Effect of the o-Methoxy Group on Reactivity and Reaction Mechanism. J Org Chern 2011, 110812095428021. <http://dx.doi.org/10.1021/jo201387h>
  • Im Li-Ra, Jeon Sang-Eun, Um Ik-Hwan: Aminolysis of S-4-Nitrophenyl X-Substituted Thiobenzoates: Effect of Nonleaving-Group Substituents on Reactivity and Mechanism. Bulletin of the Korean Chemical Society 2011, 32, 1153. <http://dx.doi.org/10.5012/bkcs.2011.32.4.1153>
  • Son Min-Ji, Kim Song-I, Um Ik-Hwan: Pyridinolysis of 2,4-Dinitrophenyl Phenyl Thionocarbonate: Effect of Changing Electrophilic Center from C=O to C=S on Reactivity and Mechanism. Bulletin of the Korean Chemical Society 2011, 32, 1165. <http://dx.doi.org/10.5012/bkcs.2011.32.4.1165>
  • Lee Jong-Pal, Bae Ae-Ri, Um Ik-Hwan: Kinetic Study on Aminolysis of 4-Pyridyl X-Substituted Benzoates: Effect of Substituent X on Reactivity and Reaction Mechanism. Bull Kor Chem Soc 2011, 32, 1907. <http://dx.doi.org/10.5012/bkcs.2011.32.6.1907>
  • Im Li-Ra, Min Ji-Sook, Akhtar Kalsoom, Um Ik-Hwan: Aminolysis of 2,4-Dinitrophenyl and 3,4-Dinitrophenyl Diphenylphosphinothioates: Steric Hindrance versus Nucleofugality in Nucleophilic Substitution Reactions. Bull Kor Chem Soc 2011, 32, 2117. <http://dx.doi.org/10.5012/bkcs.2011.32.6.2117>
  • Kim Chae-Won, Lee Jae-In, Um Ik-Hwan: Aminolysis of Y- Substituted Phenyl Benzenesulfonates in MeCN: Effect of Medium on Reactivity and Reaction Mechanism. Bull Kor Chem Soc 2011, 32, 2955. <http://dx.doi.org/10.5012/bkcs.2011.32.8.2955>
  • Kanzian Tanja, Mayr Herbert: Electrophilic Reactivities of Azodicarboxylates. Chem Eur J 2010, 16, 11670. <http://dx.doi.org/10.1002/chem.201001598>
  • Kim Mi-Hyang, Chi Yong-Seok, Han Jae-Hong: A New Stereoisomer of Mn(II) Tris(2-Pyridylmethyl)amine Complex, [TPA2Mn](ClO4)2. Bulletin of the Korean Chemical Society 2010, 31, 23. <http://dx.doi.org/10.5012/bkcs.2010.31.01.023>
  • Um Ik-Hwan, Akhtar Kalsoom: Piperidinolysis of 4-Nitrophenyl X-Substituted Benzenesulfonates and Related Compounds: Effect of Changing Leaving Group and Electrophilic Center. Bulletin of the Korean Chemical Society 2010, 31, 234. <http://dx.doi.org/10.5012/bkcs.2010.31.01.234>
  • Um Ik-Hwan, Son Min-Ji, Kim Song-I, Akhtar Kalsoom: Pyridinolyses of 2,4-Dinitrophenyl Phenyl Carbonate and 2,4-Dinitrophenyl Benzoate: Effect of Nonleaving Group on Reactivity and Mechanism. Bulletin of the Korean Chemical Society 2010, 31, 1915. <http://dx.doi.org/10.5012/bkcs.2010.31.7.1915>
  • Castro Enrique A.: ChemInform Abstract: Kinetics and Mechanism of the Aminolysis of Thioesters and Thiocarbonates in Solution. ChemInform 2009, 40. <http://dx.doi.org/10.1002/chin.200928263>
  • Kanzian Tanja, Nigst Tobias A., Maier Andreas, Pichl Stefan, Mayr Herbert: Nucleophilic Reactivities of Primary and Secondary Amines in Acetonitrile. Eur J Org Chem 2009, 2009, 6379. <http://dx.doi.org/10.1002/ejoc.200900925>