Design and evaluation of semicarbazide-embeddedd stationary phases for liquid chromatography

J Chromatogr A. 2024 Apr 12:1720:464782. doi: 10.1016/j.chroma.2024.464782. Epub 2024 Mar 1.

Abstract

Semicarbazide, as a derivative of urea, constitutes a great variety of functional molecules for different needs. Herein, novel stationary phases with an incorporated semicarbazide group were proposed. Using aliphatic (docosanoyl, C22) and aromatic (benzoyl, Bz) hydrazides, the semicarbazide-embedded ligands were synthesized before chemical modification of the silica gel, allowing for an accurate interpretation of the chromatographic properties of the corresponding packings. The new stationary phases were water-wettable, due to the presence of highly polar groups. In particular, Bz-semicarbazide (Bz-SCD) stationary phase was sufficiently hydrophilic to run in hydrophilic interaction (HILIC) mode, whilst the C22 (C22-SCD) equivalent, in spite of its reversed-phase nature, was markedly less hydrophobic than the referenced polar-embedded ones. The versatility of C22-SCD was demonstrated with a large selection of analytes, including geometric isomers and standard mixtures of polycyclic aromatic hydrocarbons, sulfonamides, sulfonylurea, substituted ureas, pyridines and carbamates, fat-soluble colorants, antifungal metabolites, angiotensin II receptor blockers and calcium channel blockers.

Keywords: Hydrazide; Polar-embedded; Retention mechanisms; Semicarbazide; Stationary phase.

MeSH terms

  • Chromatography, Liquid / methods
  • Chromatography, Reverse-Phase*
  • Hydrophobic and Hydrophilic Interactions
  • Isomerism
  • Semicarbazides*
  • Silicon Dioxide* / chemistry

Substances

  • carbamylhydrazine
  • Silicon Dioxide
  • Semicarbazides