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Open AccessFeature PaperArticle

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

1
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bldg. 9, 1113 Sofia, Bulgaria
2
Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark
3
Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland
*
Author to whom correspondence should be addressed.
Dedicated to Prof. Bernd Giese on Behalf of His 80th Birthday.
Chemistry 2020, 2(2), 374-389; https://doi.org/10.3390/chemistry2020024
Received: 14 April 2020 / Revised: 24 April 2020 / Accepted: 30 April 2020 / Published: 4 May 2020
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. View Full-Text
Keywords: rotary switch; UV-Vis spectroscopy; NMR; DFT; X-ray; aggregation rotary switch; UV-Vis spectroscopy; NMR; DFT; X-ray; aggregation
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Hristova, S.; Kamounah, F.S.; Crochet, A.; Vassilev, N.; Fromm, K.M.; Antonov, L. OH Group Effect in the Stator of β-Diketones Arylhydrazone Rotary Switches. Chemistry 2020, 2, 374-389.

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