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Issue 23, 2010
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Synthesis, structural and conformational properties, and gas phase reactivity of 1,4-dihydropyridine ester and ketone derivatives

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Abstract

A new series of 4-aryl-2,6-dimethyl-1,4-dihydropyridines, characterized by ester or ketone functions at positions 3 and 5, has been synthesized. Structural and conformational properties, concerning the dihydropyridine ring and the orientation (synplanar/antiperiplanar) of the substituents have been investigated in their crystal structure and in solution by nuclear magnetic resonance. Evaluation of intermolecular and hydrogen bonding interactions as well as packing features, have been also carried out, evidencing interesting packing motifs. Their gas phase reactivity, as protonated and deprotonated molecules, has been investigated by electrospray ionization, high resolution and collision-induced dissociation multiple stage mass spectrometry. Deydrogenation reactions have been observed as a function of the capillary voltage.

Graphical abstract: Synthesis, structural and conformational properties, and gas phase reactivity of 1,4-dihydropyridine ester and ketone derivatives

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Article information


Submitted
26 Jul 2010
Accepted
23 Aug 2010
First published
27 Sep 2010

Org. Biomol. Chem., 2010,8, 5339-5344
Article type
Paper

Synthesis, structural and conformational properties, and gas phase reactivity of 1,4-dihydropyridine ester and ketone derivatives

G. Giorgi, M. F. A. Adamo, F. Ponticelli and A. Ventura, Org. Biomol. Chem., 2010, 8, 5339
DOI: 10.1039/C0OB00494D

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