Issue 5, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Conformations of vicinal-triketones. A theoretical and 17O NMR approach

Giovanni Cerioni,*a   Antonio Plumitallo,a   Francesca Mocci,b   Zvi Rappoportc  and  Mordecai B. Rubind  

* Corresponding authors

a Dipartimento Farmaco Chimico Tecnologico, Cagliari University, Via Ospedale 72, Cagliari, Italy

b Dipartimento di Scienze Chimiche, Cagliari University, Cittadella Universitaria di Monserrato, SS 554 Bivio per Sestu, Monserrato (CA), Italy

c Department of Organic Chemistry and the Lise Meitner Minerva Center for Computational Quantum Chemistry, The Hebrew University of Jerusalem, Jerusalem, Israel

d Department of Chemistry, Technion-Israel Institute of Technology, Haifa, Israel

Abstract

The conformations of a representative group of vicinal triketones have been studied by 17O NMR spectroscopy and, for some of them, DFT calculations have been performed in order to rationalize the results and gain an insight into their geometry; 17O NMR chemical shifts have also been computed by the GIAO method. A dependence of chemical shifts on intercarbonyl dihedral angles, like that observed for α-dicarbonyl systems, has been observed. A constraint to changing conformation, which overrides steric destabilization, has also been observed.

Graphical abstract: Conformations of vicinal-triketones. A theoretical and 17O NMR approach

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B009848P
Article type
Paper
Submitted
07 Dec 2000
Accepted
14 Mar 2001
First published
10 Apr 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 774-777

Permissions

Request permissions

Conformations of vicinal-triketones. A theoretical and 17O NMR approach

G. Cerioni, A. Plumitallo, F. Mocci, Z. Rappoport and M. B. Rubin, J. Chem. Soc., Perkin Trans. 2, 2001, 774 DOI: 10.1039/B009848P

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.

Spotlight

Advertisements