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Issue 24, 2010
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The influence of protonation on molecular structure and physico-chemical properties of gossypolSchiff bases

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Abstract

Protonation of gossypol Schiff bases (S1 and S2), possessing different numbers of basic N-atoms, was studied using potentiometric, spectroscopic, ESI MS and PM5 methods. Titration of S1 and S2 with HClO4, monitored by the FT-IR and 1H NMR, indicated that the change from the enamine-enamine into the protonated imine-imine tautomeric form occurs at different Schiff baseH+ ratio. The FT-IR and PM5 results show that for S1 the first protonation step occurs at Schiff base moiety whereas for S2 it is realised at N-atom of the morpholine. The formation of N+H⋯O hydrogen bond between morpholine moieties within S2 contributes to high pKa(ACN) = 22.65.

Graphical abstract: The influence of protonation on molecular structure and physico-chemical properties of gossypol Schiff bases

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Publication details

The article was received on 18 Jun 2010, accepted on 08 Sep 2010 and first published on 19 Oct 2010


Article type: Paper
DOI: 10.1039/C0OB00288G
Org. Biomol. Chem., 2010,8, 5511-5518

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    The influence of protonation on molecular structure and physico-chemical properties of gossypol Schiff bases

    P. Przybylski, K. Pyta, J. Czupryniak, B. Wicher, M. Gdaniec, T. Ossowski and B. Brzezinski, Org. Biomol. Chem., 2010, 8, 5511
    DOI: 10.1039/C0OB00288G

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