Issue 4, 2011
From the journal:

Chemical Communications

Polycyclic croissant-like organic compounds are powerful superbases in the gas phase and acetonitrile—a DFT study†

Nena Perana  and  Zvonimir B. Maksić*a  

* Corresponding authors

a Quantum Organic Chemistry Group, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10 000 Zagreb, Croatia
E-mail: zmaksic@spider.irb.hr
Fax: +385 1 4561118
Tel: +385 1 4561117

Abstract

A new type of the π-electron polycyclic organic superbases is proposed exhibiting very high proton affinities in the gas phase spanning the range from 280 to 323 kcal mol−1 and the pKa up to 41.4 units in the MeCN solutions. Their salient feature is formation of the (H+)-bridge upon protonation and a strong cationic resonance effect in the corresponding conjugate acids.

Graphical abstract: Polycyclic croissant-like organic compounds are powerful superbases in the gas phase and acetonitrile—a DFT study

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Article information

DOI
https://doi.org/10.1039/C0CC03386C
Article type
Communication
Submitted
20 Aug 2010
Accepted
05 Nov 2010
First published
24 Nov 2010

Chem. Commun., 2011,47, 1327-1329

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Polycyclic croissant-like organic compounds are powerful superbases in the gas phase and acetonitrile—a DFT study

N. Peran and Z. B. Maksić, Chem. Commun., 2011, 47, 1327 DOI: 10.1039/C0CC03386C

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