Issue 4, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Low barrier hydrogen bonds in sterically modified Schiff bases

Aleksander Filarowski,*a   Aleksander Kolla  and  Tadeusz Glowiaka  

* Corresponding authors

a Faculty of Chemistry, University of Wroclaw, 14 F. Joliot-Curie str., Wroclaw, Poland

Abstract

Five derivatives of an ortho-hydroxy Schiff base (2-(N-alkyl-α-iminoethyl)phenols) with very short intramolecular hydrogen bonds (dO(H)⋯N ≤ 2.500 Å) were synthesised. The crystal structures were determined. The steric repulsion of the substituted methyl group results in an unusual strengthening of the hydrogen bonds, decreasing the barrier for the proton movement within the hydrogen bridge, which leads to a delocalization of the proton position. The very strong influence of the character of the substituent in the phenol ring as well as the character of the N-alkyl chain on the proton distribution is demonstrated for these hydrogen bonds from the so-called inversion range.

Graphical abstract: Low barrier hydrogen bonds in sterically modified Schiff bases

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Article information

DOI
https://doi.org/10.1039/B106145N
Article type
Paper
Submitted
11 Jul 2001
Accepted
18 Feb 2002
First published
06 Mar 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 835-842

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Low barrier hydrogen bonds in sterically modified Schiff bases

A. Filarowski, A. Koll and T. Glowiak, J. Chem. Soc., Perkin Trans. 2, 2002, 835 DOI: 10.1039/B106145N

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