Click N-benzyl iminodiacetic acid: Novel silica-based tridentate zwitterionic stationary phase for hydrophilic interaction liquid chromatography

Iminodiacetic acid (IDA) is dicarboxylic acid amine, which may produce stronger interaction with polar or charged compounds than bidentate alpha,beta-amino acid. In this article, a novel type of tridentate zwitterionic HILIC stationary phase was prepared by covalently bonding N-benzyl IDA on silica gel via copper(I) catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition (CuAAC). The structure of this stationary phase and all related intermediates was confirmed by NMR, FT-IR, MS spectrum and elemental analysis. The new stationary phase showed good HILIC characteristics and high column efficiency (the theoretical plate number is up to 44000 plates m(-1) in the case of guanosine) in the application of separation of polar compounds, including organic acids, organic bases, as well as highly polar and hydrophilic compounds, such as cephalosporins and carbapenems. Most of them displayed good peak shape and selectivity. (C) 2014 Elsevier B.V. All rights reserved.