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Licensed Unlicensed Requires Authentication Published by De Gruyter (O) December 3, 2014

Influence of pressure on molecular packing and photochemical properties in three chalcone analogs

  • Julia Bąkowicz , Tomasz Galica and Ilona Turowska-Tyrk EMAIL logo

Abstract

The structures of 1-(4-methylphenyl)-3-(2-thienyl)prop-2-en-1-one, (I), 1-(5-bromo-2-hydroxyphenyl)-3-(2-furyl)prop-2-en-1-one, (II), and 1-(3-furyl)-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one, (III), were determined in ambient and high pressure conditions. The values of the intermolecular geometrical parameters describing possibilities of execution of [2+2] photodimerization were calculated and analysed. In the case of ambient pressure, for (I) they are close to the border valid for photoreactive compounds and for (II) and (III) they exclude the photochemical reaction in crystals. High pressure hardly changed the mutual orientation of adjacent molecules and largely the distance between them: in the case of (I), the distance was far below limits for compounds undergoing [2+2] photodimerization. The volume of free space was calculated for the studied compounds for different values of pressure and analysed in the context of possibilities of the [2+2] photodimerization.


Corresponding author: Ilona Turowska-Tyrk, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland, E-mail:

Acknowledgments

This work was financed by the National Science Centre, Poland, grant 2011/01/D/ST5/02834. The authors are grateful to Dr. Jacek Wojaczyński for recording 1H NMR spectra of compounds (I) and (II).

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Supplemental Material

The online version of this article (DOI: 10.1515/zkri-2014-1792) offers supplementary material, available to authorized users.


Received: 2014-7-28
Accepted: 2014-10-27
Published Online: 2014-12-3
Published in Print: 2015-2-1

©2015 by De Gruyter

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