Characterization of anthraquinone-2-carbonyl chloride as an alcohol derivatization reagent for negative ion chemical ionization mass spectrometry

Abstract

Anthraquinone-2-carbonyl chloride has been utilized as a derivatization reagent for alcohols to impart electron affinity and aid in transport via a particle beam liquid chromatography-mass spectrometry (LC/MS) interface. In addition, the gas chromatographic-mass spectrometry, UV, fluorescence, and electrochemical characteristics of the derivatives were determined. A series of model compounds, 2-phenylethanol (phenethyl alcohol), 1-phenyl-2-propanol, 2-methyl-l-phenyl-2-propanol, hexanol, and methyl 2-methylglycerate, were used as analytes.The particle beam LC/MS properties of the resultant anthraquinone carboxylate esters were determined in electron impact (EI) and negative ion chemical ionization (NCI) modes. The NCI responses of these anthraquinone carboxylate esters were compared with the corresponding 3,5-dinitrobenzoate esters. The anthraquinone carboxylate esters exhibited an NCI to EI sensitivity enhancement of 113 and were detected in NCI at a tenfold lower concentration than the corresponding 3,5-dinitrobenzoate esters. A detection limit of 26 pg injected on column was achieved for phenethyl anthraquinone carboxylate in NCI by using selected ion monitoring.