Issue 23, 2010

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

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

Supplementary files

Article information

Article type
Paper
Submitted
26 Jul 2010
Accepted
23 Aug 2010
First published
27 Sep 2010

Org. Biomol. Chem., 2010,8, 5339-5344

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements