Issue 10, 2002
From the journal:

New Journal of Chemistry

In search of neutral organic superbases—iminopolyenes and their amino derivatives

Robert Vianello,a   Borislav Kovačevića  and  Zvonimir B. Maksić*ab  

* Corresponding authors

a Quantum Organic Chemistry Group, Ruđer Bošković Institute, Zagreb, Croatia
E-mail: zmaksic@spider.irb.hr
Fax: +385 1 4561118
Tel: +385 1 4561117

b Faculty of Science and Mathematics, The University of Zagreb, Marulićev trg 19, Zagreb, Croatia

Abstract

The intrinsic proton affinities of iminopolyenes and their amino derivatives are considered. It is shown that substitution of amino groups at strategic positions increases proton affinity (PA) to superbasic values particularly in branched polyenes. It follows that the number of double bonds, selection of the conformations and a judicious choice of substituents offer a closely spaced ladder of highly basic compounds spanning the range of values of PAs between 206.5 and 271.9 kcal mol−1, which might be of some importance in acid–base chemistry. This conclusion is strengthened by the fact that several of the studied amino derivatives of iminopolyenes exhibit very high pKa values between 30.0–33.5 in acetonitrile. Hence, they qualify as candidates for powerful neutral organic superbases.

Graphical abstract: In search of neutral organic superbases—iminopolyenes and their amino derivatives

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Article information

DOI
https://doi.org/10.1039/B203475A
Article type
Paper
Submitted
09 Apr 2002
Accepted
16 May 2002
First published
15 Aug 2002

New J. Chem., 2002,26, 1324-1328

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In search of neutral organic superbases—iminopolyenes and their amino derivatives

R. Vianello, B. Kovačević and Z. B. Maksić, New J. Chem., 2002, 26, 1324 DOI: 10.1039/B203475A

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