Structure-retention relationships in the gas chromatography of N,N- dialkylhydrazones

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Abstract

N,N-Dialkylhydrazones [DAHs; R1R2C = 1N-2N(R3)2] were prepared and their Kovats retention indices determined on 100% dimethylpolysiloxane (HP- 1) and 5% diphenyl and 95% dimethylpolysiloxane (HP-5) stationary phases. The physico-chemical and retention behaviour of the DAHs depend greatly on whether R2 = H or an alkyl group. A similar difference is observed in the alkane and oxo homomorphic factors of DAHs formed from aldehydes or ketones. The difference is explained on the basis of NMR and quantum-chemical results by intramolecular interactions between R2 and the lone pair of the 2N atom. A single linear equation is suitable for prediction of retention indices if parameters are introduced representing resonance structure (bond angle and electron density) besides I(oxo) or the van der Waals' surface.

Original languageEnglish
Pages (from-to)653-659
Number of pages7
JournalChromatographia
Volume42
Issue number11-12
DOIs
Publication statusPublished - Aug 10 1996

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Keywords

  • Dialkylhydrazones
  • Gas chromatography
  • Kovats retention indices
  • Structure- retention relationships

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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