Ionization constants of N-acyl derivatives of glycine

  • Yu. I. Khurgin
  • I. V. Vikha
Physical Chemistry
Received:
  • 35 Downloads

Conclusions

  1. 1.

    The ionization constant of a number of N-acylated derivatives of glycine with acyl substituents of different types were measured by the method of potentiometric titration.

     
  2. 2.

    A quantitative explanation of the inductive effect of the substituent in the acyl group was performed with the aid of the Taft correlation equation. The reaction constant of ionizationρ* was measured.

     
  3. 3.

    The constants of transmission of the inductive effect through the amide group were estimated: an estimate of the transmission through the nitrogen atom ZNH=0.36 was given within the framework of the additive scheme.

     
  4. 4.

    For substituents bonded with an amide bond to an atom with increased electron density, and for charged substituents, a deviation from the correlation dependence is observed. A discussion of the mechanism of the interaction of the substituents with the reaction center or with the amide bond, which, causes the deviations, is cited.

     
  5. 5.

    The data obtained can be used for a preliminary calculation of the relative reaction rates of amino acids with various protective groups in reactions of peptide synthesis.

     

Keywords

Nitrogen Atom Potentiometric Titration Inductive Effect Amide Bond Peptide Synthesis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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Copyright information

© Consultants Bureau 1969

Authors and Affiliations

  • Yu. I. Khurgin
    • 1
  • I. V. Vikha
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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