Issue 4, 2009
From the journal:

New Journal of Chemistry

The engineering of powerful non-ionic superacids in silico—a DFT-B3LYP study of open chain polycyanopolyenes

Robert Vianello*a  and  Zvonimir B. Maksićab  

* Corresponding authors

a Quantum Organic Chemistry Group, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, POB 180, Croatia
E-mail: vianello@irb.hr
Fax: +385 1 4561118
Tel: +385 1 4561117

b Faculty of Science, University of Zagreb, Marulićev trg 19, Croatia

Abstract

The acidity of a number of all-trans polyenes, and some of their phenyl and naphthyl derivatives, was examined by the B3LYP/6-311+G(2d,p)//B3LYP/6-31G(d) method. A dramatic increase in their acidity was established upon multiple cyanation. The origin of the acidity amplification was identified as the increased stability of the resulting conjugate bases, which is mirrored in Koopmans' term appearing in the triadic analysis. It is important to emphasize that many of the studied polycyano compounds have already been synthesized. Others are probably synthesizable and their preparation is strongly recommended. Some of the examined systems come close to the acidity threshold of 245 kcal mol−1 that characterizes hyperacids. The acidity of different tautomeric forms of the same organic acid is briefly discussed.

Graphical abstract: The engineering of powerful non-ionic superacids in silico—a DFT-B3LYP study of open chain polycyanopolyenes

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Article information

DOI
https://doi.org/10.1039/B816922E
Article type
Paper
Submitted
30 Sep 2008
Accepted
03 Nov 2008
First published
22 Dec 2008

New J. Chem., 2009,33, 739-748

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The engineering of powerful non-ionic superacids in silico—a DFT-B3LYP study of open chain polycyanopolyenes

R. Vianello and Z. B. Maksić, New J. Chem., 2009, 33, 739 DOI: 10.1039/B816922E

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