OH Group Effect in the Stator of β-Diketones Arylhydrazone Rotary Switches
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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.
Originalsprog | Engelsk |
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Tidsskrift | Chemistry |
Vol/bind | 2 |
Udgave nummer | 2 |
Sider (fra-til) | 374-389 |
Antal sider | 16 |
ISSN | 2624-8549 |
DOI | |
Status | Udgivet - jun. 2020 |
ID: 289458616