Structure-retention relationships in the gas chromatography of N,N-dialkylhydrazones
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N,N-Dialkylhydrazones [DAHs; R1R2C=1N-2N(R3)2] were prepared and their Kováts 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 the2N atom. A single linear equation is suitable for prediction of retention indices if parameters are introduced representing resonance structure (bond angle and electron density) besidesIoxo or the van der Waals' surface.
Key WordsGas chromatography Dialkylhydrazones Kováts retention indices Structure-retention relationships
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