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Volumn 2009, Issue 6, 2009, Pages 15-29

Substituent effects on the mechanism changeover in a multipathway reaction: A model for the behavior of biological systems?

Author keywords

Acid catalysis; Base catalysis; Changeover of mechanism; Model for enzymes; Monocyclic rearrangements; Multi pathway reactions

Indexed keywords


EID: 67649513117     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0010.603     Document Type: Article
Times cited : (1)

References (79)
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    • Chemical Reviews has dedicated an issue to the Chemistry of heterocyclic compounds (Katritzky, A. R., Ed. Chem. Rev. 2004, 104, 2125) well evidencing their role in organic synthesis.
    • (d) Chemical Reviews has dedicated an issue to the Chemistry of heterocyclic compounds (Katritzky, A. R., Ed. Chem. Rev. 2004, 104, 2125) well evidencing their role in organic synthesis.
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    • An operational pH scale, pS, see Bates, R. G. Solute-Solvent Interactions; Coetze, J. F, Ritchie, C. D, Eds, Marcel Dekker: New York, 1969; p 46, was established in aqueous dioxane by employing the pKa values of acids determined by interpolation from the data reported by H. S. Harned and B. B. Owen The Physical Chemistry of Electrolytic Solution, 3rd ed, ACS Monograph No. 137; Reinhold: New York, 1970; pp 716, 755, For details see ref. 9a
    • a values of acids determined by interpolation from the data reported by H. S. Harned and B. B. Owen (The Physical Chemistry of Electrolytic Solution, 3rd ed.; ACS Monograph No. 137; Reinhold: New York, 1970; pp 716, 755). For details see ref. 9a.
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    • Recently Terrier and Coworkers (Mokhtari, M.; Goumont, R.; Hallé, J. C.; Terrier, F. Arkivoc, 2002, 168) have illustrated a nice example of pH-dependent multiform catalysis examining the covalent hydration of a benzofuroxan derivative.
    • Recently Terrier and Coworkers (Mokhtari, M.; Goumont, R.; Hallé, J. C.; Terrier, F. Arkivoc, 2002, 168) have illustrated a nice example of pH-dependent multiform catalysis examining the covalent hydration of a benzofuroxan derivative.
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    • 2H-1,2,3-Triazole is much more aromatic than 1,2,4-oxadiazole aromaticity indexes: IA, 109 and 48, respectively. From Bird, C. W. Tetrahedron, 1992, 48, 335
    • A, 109 and 48, respectively. From Bird, C. W. Tetrahedron, 1992, 48, 335).
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    • In the rearrangement of (Z)-hydrazones 3a-k into the triazoles 4a-k the presence of an amido group at C(4) in the final 1,2,3-triazole ring was found to play a parallel favorable role.4,9,13
    • In the rearrangement of (Z)-hydrazones 3a-k into the triazoles 4a-k the presence of an amido group at C(4) in the final 1,2,3-triazole ring was found to play a parallel favorable role.4,9,13
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    • See ref. 11i, p 496
    • (a) See ref. 11i, p 496.
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    • A,R of the concerned reactions the relationships as a function of the present substituents would be regarded as FERs.
    • A,R of the concerned reactions the relationships as a function of the present substituents would be regarded as FERs.
  • 77
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    • n) for the optimized FER relationships being compared herein should not significantly affect the values of the susceptibility constants involved.9j
    • n) for the optimized FER relationships being compared herein should not significantly affect the values of the susceptibility constants involved.9j


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