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  • 1. Dybala-Defratyka, Agnieszka
    et al.
    Rostkowski, Michal
    Matsson, Olle
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Westaway, Kenneth C.
    Paneth, Piotr
    A New Interpretation of Chlorine Leaving Group Kinetic Isotope Effects; A Theoretical Approach2004In: J. Org. Chem., Vol. 69, p. 4900-4905Article in journal (Refereed)
    Abstract [en]

    The chlorine leaving group kinetic isotope effects (KIEs) for the SN2 reactions between methyl chloride and a wide range of anionic, neutral, and radical anion nucleophiles were calculated in the gas phase and, in several cases, using a continuum solvent model. In contrast to the expected linear dependence of the chlorine KIEs on the Ca-CI bond order in the transition state, the KIEs fell in a very small range (1.0056-1.0091), even though the Ca-CI transition state bond orders varied widely from approximately 0.32 to 0.78, a range from reactant-like to very product-like. This renders chlorine KIEs, and possibly other leaving-group KIEs, less useful for studies of reaction mechanisms than commonly assumed. A partial explanation for this unexpected relationship between the Ca-CI transition state bond order and the magnitude of the chlorine KIE is presented.

  • 2.
    Zhang, Suode
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Avd för organisk kemi.
    Govender, Thavendran
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Avd för organisk kemi.
    Norström, Thomas
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Avd för organisk kemi.
    Arvidsson, Per
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Avd för organisk kemi.
    An Improved Synthesis of Fmoc-N-methyl-a-amino Acids2005In: J. Org. Chem., no 70, p. 6918-6920Article in journal (Refereed)
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