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1 article(s) from Nénon, Sébastien

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

Arnault Heynderickx,
Sébastien Nénon,
Olivier Siri,
Vladimir Lokshin and
Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2019, 15, 2059–2068, doi:10.3762/bjoc.15.203

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Graphical Abstract

Figure 1: Quinoxaline derivatives 1–3.

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Scheme 1: Synthesis of THTTA (3).

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Scheme 2: Protonation, alkylation and acylation of 3.

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Figure 2: The ORTEP view of 3. Torsion angles within the benzene ring are given in red.

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Figure 3: The ORTEP view of 6a. Torsion angles within the benzene ring are given in red.

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Figure 4: The ORTEP view of 7a (the iodine counter anion has been omitted for clarity). Torsion angles within...

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Scheme 3: Charge transfer and delocalization within 3 and its diprotonated (6a) and monomethylated (7a) deriv...

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Figure 5: Normalized absorption spectra of 3 in: toluene (black), acetone (blue), ethanol (green), water (red...

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Figure 6: Protonation of 3 in ethanol. Two isosbestic points (IBP) are indicated by arrows.

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Figure 7: Absorption spectra of 7a (blue) and 8 (red) in ethanol.

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Figure 8: Absorption spectra of 10a (black), 10b (red). Solid curves: in toluene, dashed curves: in acetone.

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Figure 9: View of the supramolecular array generated by 3 in the solid state. Color coding: nitrogen, blue; c...

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Figure 10: View of the supramolecular array generated by 6a in the solid state. Color coding: nitrogen, blue; ...

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Figure 11: View of the supramolecular array generated by 7a in the solid state. Color coding: nitrogen, blue; ...

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Published 28 Aug 2019

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