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OH Group Effect in the Stator of β-Diketones Arylhydrazone Rotary Switches

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Hristova Silvia, Kamounah Fadhil S., Crochet Aurelien, Vassilev Nikolay, Fromm Katharina M., Antonov Liudmil,
Project Single Crystal Diffraction: Dual System
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Original article (peer-reviewed)

Journal Chemistry
Volume (Issue) 2(2)
Page(s) 374 - 389
Title of proceedings Chemistry
DOI 10.3390/chemistry2020024

Open Access

URL http://doi.org/10.3390/chemistry2020024
Type of Open Access Publisher (Gold Open Access)

Abstract

The properties of several hydrazon-diketone rotary switches with OH groups in the stators (2-(2-(2-hydroxy-4-nitrophenyl)hydrazono)-1-phenylbutane-1,3-dione, 2-(2-(2-hydroxyphenyl)hydrazono)-1-phenylbutane-1,3-dione and 2-(2-(4-hydroxyphenyl)hydrazono)-1-phenylbutane-1,3-dione) were investigated by molecular spectroscopy (UV-Vis and NMR), DFT calculations (M06-2X/TZVP) and X-ray analysis. The results show that, when the OH group is in ortho position, the E’ and Z’ isomers are preferred in DMSO as a result of a stabilizing intermolecular hydrogen bonding with the solvent. The availability, in addition, of a nitro group in para position increases the possibility of deprotonation of the OH group in the absence of water. All studied compounds showed a tendency towards formation of associates. The structure of the aggregates was revealed by theoretical calculation and confirmed by X-ray analysis.
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