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  • Title: Substituent effect on electron affinity, gas-phase basicity, and structure of monosubstituted propynyl radicals and their anions: a theoretical study.
    Author: Lee GY.
    Journal: J Comput Chem; 2009 Nov 15; 30(14):2181-6. PubMed ID: 19242956.
    Abstract:
    The substituent effect of electron-withdrawing groups on electron affinity and gas-phase basicity has been investigated for substituted propynl radicals and their corresponding anions. It is shown that when a hydrogen of the alpha-CH(3) group in the propynyl system is substituted by an electron-withdrawing substituent, electron affinity increases, whereas gas-phase basicity decreases. These results can be explained in terms of the natural atomic charge of the terminal acetylene carbon of the systems. The calculated electron affinities are 3.28 eV (*C=C-CH(2)F), 3.59 eV (*C[triple bond]C-CH(2)Cl) and 3.73 eV (*C[triple bond]C-CH(2)Br), and the gas-phase basicities of their anions are 359.5 kcal/mol ((-):C[triple bond]C-CH(2)F), 354.8 kcal/mol (:C[triple bond]C-CH(2)Cl) and 351.3 kcal/mol ((-):C[triple bond]C-CH(2)Br). It is concluded that the larger the magnitude of electron-withdrawing, the greater is the electron affinity of radical and the smaller is the gas-phase basicity of its anion.
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