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Croatica Chemica Acta, Vol. 90 No. 4, 2017.

Original scientific paper

https://doi.org/10.5562/cca3339

Solid-State Supramolecular Assembly of Salicylic Acid and 2-Pyridone, 3-Hydroxypyridine or 4-Pyridone

Stipe Lukin ; Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000 Zagreb, Croatia
Tomislav Stolar ; Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000 Zagreb, Croatia
Martina Tireli ; Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000 Zagreb, Croatia
Dajana Barišić ; Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000 Zagreb, Croatia
Marco di Michiel ; ESRF - the European Synchrotron, 71 Avenue des Martyrs, 38000 Grenoble, France
Krunoslav Užarević ; Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000 Zagreb, Croatia
Ivan Halasz orcid id orcid.org/0000-0002-5248-4217 ; Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička c. 54, HR-10000 Zagreb, Croatia

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Abstract

Mechanochemical milling of equimolar mixtures of salicylic acid with three hydroxy derivatives of pyridine provided three new phases. With 2-hydroxypyridine, which is in fact present as 2-pyridone, a discrete cocrystal supramolecular assembly is formed. 3-hydroxypyridine and salicylic acid formed a salt and an extended network of hydrogen bonds while the product of the reaction of 4-hydroxypyridine (present as 4-pyridone) and salicylic acid remained structurally uncharacterized. All three hydroxypyridines retain the tautomeric form as in their respective pure phases upon cocrystal formation. Where possible, reaction profiles have been extracted from in situ monitoring via Rietveld refinement to show direct product formation which could be well described using the first-order reaction rate law.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

cocrystal; mechanochemistry; in situ monitoring; salicylic acid; hydroxypyridine

Hrčak ID:

199170

URI

https://hrcak.srce.hr/199170

Publication date:

29.12.2017.

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