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Issue 30, 2013
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Insights into diastereoisomeric characterization of tetrahydropyridazine amino acid derivatives: crystal structures and gas phase ion chemistry

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Abstract

Structural, conformational properties, and gas phase reactivity of two representative diastereoisomeric members of a series of α,α-tetrahydropyridazine amino acid derivatives have been investigated by using X-ray crystallography, tandem mass spectrometry and theoretical calculations. Both diastereoisomers show an unusual screw-boat conformation of the tetrahydropyridazine ring. While protonated molecules mainly decompose in the gas phase by loss of acetamide, the main reactivity of the [M + Na]+ species consists of loss of PhNCO followed by acetamide and it is strictly dependent upon the stereochemistry of the parent compound. The most stable energy minimized structures obtained by theoretical calculations are in full agreement with the experimental data and allowed us to rationalize the gas phase reaction pathways.

Graphical abstract: Insights into diastereoisomeric characterization of tetrahydropyridazine amino acid derivatives: crystal structures and gas phase ion chemistry

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Publication details

The article was received on 18 May 2013, accepted on 24 May 2013 and first published on 24 May 2013


Article type: Paper
DOI: 10.1039/C3OB41034J
Citation: Org. Biomol. Chem., 2013,11, 5006-5011
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    Insights into diastereoisomeric characterization of tetrahydropyridazine amino acid derivatives: crystal structures and gas phase ion chemistry

    G. Giorgi, G. Favi and O. A. Attanasi, Org. Biomol. Chem., 2013, 11, 5006
    DOI: 10.1039/C3OB41034J

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