Issue 2, 2008
From the journal:

New Journal of Chemistry

Strategic design of small and versatile bicyclic organic superbases: a density functional study†

Ajeet Singha  and  Bishwajit Ganguly*a  

* Corresponding authors

a Analytical Division, Central Salt & Marine Chemicals Research Institute, Bhavnagar, 364002 Gujarat, India
E-mail: ganguly@csmcri.org
Fax: +91 278 256 7562
Tel: +91 278 256 7760

Abstract

It is shown by a reliable DFT method that bicyclic structures 7–10, constructed using 1,3-diaminopropane as an essential building block, can act as powerful neutral organic superbases in the gas phase, aqueous solution and in acetonitrile. This new molecular framework is versatile in terms of anchoring different functional groups to achieve higher basicities. The buttressing effect of substituents on the basicity of these organic bases was also observed. The proton affinities calculated at the B3LYP/6-311+G**//B3LYP/6-31+G* level for 1,2-diaminoethane and 1,3-diaminopropane were found to be in good agreement with the experimental results. Barriers for proton transfer between the N atoms of the diamine and diimine cations are also reported.

Graphical abstract: Strategic design of small and versatile bicyclic organic superbases: a density functional study

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Article information

DOI
https://doi.org/10.1039/B713499A
Article type
Paper
Submitted
04 Sep 2007
Accepted
11 Oct 2007
First published
26 Oct 2007

New J. Chem., 2008,32, 210-213

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Strategic design of small and versatile bicyclic organic superbases: a density functional study

A. Singh and B. Ganguly, New J. Chem., 2008, 32, 210 DOI: 10.1039/B713499A

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