Issue 10, 1989

Chemical ionization mass spectra of urethanes

Abstract

Chemical ionisation mass spectra using methane as the reagent gas are reported for 33 urethanes of general structure RNHCO2C2H5[R = H, CnH2n+1(n= 1–8), CH2CH[double bond, length half m-dash]CH2, cyclo-C6H11, Ph, PhCH2, PhCH2CH2, and Ph(CH3)CH] and R2NCO2C2H5[R = CnH2n+1(n= 1–4)]. Abundant MH+ ions are present in all the spectra, accompanied by satellite peaks corresponding to [M+ C2H5]+ and [M+ C3H5]+. Four classes of fragment ions are of general importance in the spectra. Two of these, [MH – C2H4]+ and [MH – C2H5OH]+, are associated with the CO2C2H5 group. The other two, corresponding to alkane and alkene elimination from MH+, arise from the RNH or R2N function. The mechanisms whereby these fragment ions are formed are discussed and their analytical utility is illustrated by reference to the spectra of the four isomeric C4H9NHCO2C2H5 and the eight isomeric C5H11NHCO2C2H5 compounds. The results of 2H-labelling studies are presented and a comparison is made between the methane and ammonia chemical ionisation spectra of selected urethanes.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1989, 1521-1528

Chemical ionization mass spectra of urethanes

A. D. Wright, R. D. Bowen and K. R. Jennings, J. Chem. Soc., Perkin Trans. 2, 1989, 1521 DOI: 10.1039/P29890001521

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