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Electron-capture sensitivity comparison of various derivatives of primary and secondary amines.

A comparative electron-capture sensitivity study was performed with various derivatives (e.g., heptafluorobutyramide, pentafluorobenzamide, and pentafluorobenzylidine) of some clinically important primary and secondary amines. Generally the order of electron-capture sensitivity for primary amines was: pentafluorobenzamide > pentafluorobenzylidine > heptafluorobutyramide, and for pentafluorobenzamides the primary amines were greater than secondary amines. Reduction of the C=O or C=N group in pentafluorobenzamide and pentafluorobenzylidine, respectively, led to a diminished response. In general, the order of sensitivity was the same but the response using a tritium detector was 10-20-fold greater than with a nickel-63 detector. The data are consistent with the theory that an electron-deficient system is necessary for good electron-capture response and that this response is also sensitive to the structure of the amine. The results further illuminate the electron-capture mechanism and suggest a more rational approach to the choice of a derivatizing agent for the determination of a particular amine.