Controlling Solvate Formation of a Schiff Base by Combining Mechano-chemistry with Solution Synthesis

A Schiff base dicarboxylic acid (1) was prepared by condensation of 2-hydroxy-1-naphthaldehyde with 5-aminoisophthalic acid. Its solvates with pyridine (2a and 2b) and dimethylformamide (3) were prepared by liquid-assisted grinding and by conventional solvent-based methods. All products were charact...

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Bibliographic Details
Published inCroatica Chemica Acta Vol. 85; no. 4; pp. 485 - 493
Main Authors Stilinović, Vladimir, Cinčić, Dominik, Zbačnik, Marija, Kaitner, Branko
Format Journal Article Paper
LanguageEnglish
Published Hrvatsko kemijsko društvo 17.12.2012
Subjects
dicarboxylic acid
mechanochemistry
Schiff base
solvates
tautomerism
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Summary:A Schiff base dicarboxylic acid (1) was prepared by condensation of 2-hydroxy-1-naphthaldehyde with 5-aminoisophthalic acid. Its solvates with pyridine (2a and 2b) and dimethylformamide (3) were prepared by liquid-assisted grinding and by conventional solvent-based methods. All products were characterised by FT-IR spectroscopy, thermogravimetric analysis and differential scanning calorimetry. The structures of 1, 2b and 3 were determined by single crystal X-ray diffraction. 1 was found to be a pure Schiff base, 2b a pyridine solvate and 3 a dimethylformamide solvate monohydrate. In all three structures, the Schiff base molecule appears to be present as the ketoamine tautomer.(doi: 10.5562/cca2111)
Bibliography:94446
ISSN:0011-1643
1334-417X
DOI:10.5562/cca2111