The use of gas-liquid chromatography (G.L.C.) for the analysis of amines of biological interest is currently under investigation in our laboratory. An intensive study of the chromatographic properties of a number of derivatives was presented by VandenHeuvel et al. (1), and this laboratory in a short communication reported on the possible use of heptafluorobutyrylated amine derivatives (2). As was noted in this early communication, sensitivity considerations must maintain priority in any proposed assay because of the extremely small quantities of these compounds present in biological fluids. For this reason, we have chosen to employ the electron capture detector (3). Trifluoroacetyl derivatives are often used in G.L.C. because of their many desirable properties. These compounds are readily synthesized and the volatile unreacted trifluoroacetic anhydride is easily removed. In addition, fully trifluoroacetylated compounds give sharp non-tailing peaks with many liquid phases. The presence of the electronegative fluorine atoms make the compounds appear at first sight to be well suited for use in conjunction with the electron-capture detector. In fact, the 0-trifluoroacetyl derivative of vanillin has furnished a very sensitive means to assay for 3-methoxy-4-hydroxy mandelic acid (V.M.A.) in urine by means of G.L.C. and electron-capture spectroscopv (4, 5). The N-trifluoroacetyl derivatives of various amines were, therefore, subjected to study using the electron-capture detector. The electron capture ability and chromatographic properties of these compounds were evaluated and compared to the monochloroacety I, pentafluoropropionyl, heptafluorobutyrl and acetyl derivatives of various amines and phenolic amines
Clarke, Donald Dudley PhD; Wilk, Sherwin; and Gitlow, Stanley E., "Electron capture properties of halogenated amine derivatives / by Donald D. Clarke, Sherwin Wilk, and Stanley E. Gitlow" (1966). Chemistry Faculty Publications. Paper 76.