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Article

Synthesis and Characterization of 1,10-Phenanthroline-mono-N-oxides

1
Department of Inorganic and Analytical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
2
Doctoral School of Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
3
MTA-DE Homogeneous Catalysis and Reaction Mechanisms Research Group, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
4
Department of Physical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: José Luis de Paz
Molecules 2021, 26(12), 3632; https://doi.org/10.3390/molecules26123632
Received: 21 May 2021 / Revised: 8 June 2021 / Accepted: 10 June 2021 / Published: 14 June 2021
(This article belongs to the Section Organic Chemistry)
N-oxides of N-heteroaromatic compounds find widespread applications in various fields of chemistry. Although the strictly planar aromatic structure of 1,10-phenanthroline (phen) is expected to induce unique features of the corresponding N-oxides, so far the potential of these compounds has not been explored. In fact, appropriate procedure has not been reported for synthesizing these derivatives of phen. Now, we provide a straightforward method for the synthesis of a series of mono-N-oxides of 1,10-phenanthrolines. The parent compounds were oxidized by a green oxidant, peroxomonosulfate ion in acidic aqueous solution. The products were obtained in high quality and at good to excellent yields. A systematic study reveals a clear-cut correlation between the basicity of the compounds and the electronic effects of the substituents on the aromatic ring. The UV spectra of these compounds were predicted by DFT calculations at the TD-DFT/TPSSh/def2-TZVP level of theory. View Full-Text
Keywords: density functional calculation; N-oxide; oxidation; peroxomonosulfate ion; X-ray diffraction density functional calculation; N-oxide; oxidation; peroxomonosulfate ion; X-ray diffraction
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MDPI and ACS Style

Najóczki, F.; Szabó, M.; Lihi, N.; Udvardy, A.; Fábián, I. Synthesis and Characterization of 1,10-Phenanthroline-mono-N-oxides. Molecules 2021, 26, 3632. https://doi.org/10.3390/molecules26123632

AMA Style

Najóczki F, Szabó M, Lihi N, Udvardy A, Fábián I. Synthesis and Characterization of 1,10-Phenanthroline-mono-N-oxides. Molecules. 2021; 26(12):3632. https://doi.org/10.3390/molecules26123632

Chicago/Turabian Style

Najóczki, Ferenc, Mária Szabó, Norbert Lihi, Antal Udvardy, and István Fábián. 2021. "Synthesis and Characterization of 1,10-Phenanthroline-mono-N-oxides" Molecules 26, no. 12: 3632. https://doi.org/10.3390/molecules26123632

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