Issue 1, 2017

Elemental steps of the thermodynamics of dihydropyrimidine: a new class of organic hydride donors

Abstract

25 Dihydropyrimidine derivatives, a new class of organo-hydrides, were designed and synthesized by the Biginelli reaction. For the first time, the thermodynamic driving forces of the six elemental steps to obtain a hydride in acetonitrile were determined by isothermal titration and electrochemical methods, respectively. The effects of molecular structures and substituents on these thermodynamic parameters were examined, uncovering some interesting structure–reactivity relationships. Both the thermodynamic and kinetic studies show that the hydride transfer from dihydropyrimidines to 9-phenylxanthylium (PhXn+ClO4) prefers a concerted mechanism.

Graphical abstract: Elemental steps of the thermodynamics of dihydropyrimidine: a new class of organic hydride donors

Supplementary files

Article information

Article type
Paper
Submitted
07 Oct 2016
Accepted
21 Nov 2016
First published
22 Nov 2016

Org. Biomol. Chem., 2017,15, 197-206

Elemental steps of the thermodynamics of dihydropyrimidine: a new class of organic hydride donors

F. Meng and X. Zhu, Org. Biomol. Chem., 2017, 15, 197 DOI: 10.1039/C6OB02195F

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