Two Roomtemperature‐stable Trications – Triprotonated Triamino‐ and Tricyanobenzene

Protonation of 1,3,5‐tricyano‐ and 1,3,5‐triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective trinitrilium and triammonium species. Furthermore, the respective N‐methyl nitrilium species was synthesized by methylation. Characterization was performed...

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Published in:	ChemistryOpen (Weinheim) Vol. 11; no. 5; pp. e202200049 - n/a
Main Authors:	Nitzer, Alexander, Hübsch, Robert, Jessen, Christoph, Kornath, Andreas J.
Format:	Journal Article
Language:	English
Published:	Germany John Wiley & Sons, Inc 01-05-2022 John Wiley and Sons Inc Wiley-VCH
Subjects:	Crystal structure Equilibrium Fluorides Nitrogen NMR Nuclear magnetic resonance Protonation Quantum chemistry Solvents spectroscopy Sulfur superacid triaminobenzene trication tricyanobenzene triaminobenzene spectroscopy superacid tricyanobenzene trication
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Abstract	Protonation of 1,3,5‐tricyano‐ and 1,3,5‐triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective trinitrilium and triammonium species. Furthermore, the respective N‐methyl nitrilium species was synthesized by methylation. Characterization was performed by NMR and vibrational spectroscopy, followed by single‐crystal X‐ray diffraction analyses of selected species. Fourfold protonation of the amine, which would have led to the triammonium arenium species, could not be achieved. Quantum chemical calculations are employed to enable full vibrational assignment as well to quantify charge localization. Triprotonation of 1,3,5‐tricyanobenzene and 1,3,5‐triaminobenzene was achieved in (super)acidic media. The nitrile species was also successfully trimethylated. Characterization of and comparison between the three trications have been carried out by vibrational and NMR spectroscopy as well as by single‐crystal X‐ray diffraction. The influence of protonation or methylation on the systems is evaluated and compared to predictions made by quantum‐chemical calculations.
AbstractList	Protonation of 1,3,5‐tricyano‐ and 1,3,5‐triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective trinitrilium and triammonium species. Furthermore, the respective N‐methyl nitrilium species was synthesized by methylation. Characterization was performed by NMR and vibrational spectroscopy, followed by single‐crystal X‐ray diffraction analyses of selected species. Fourfold protonation of the amine, which would have led to the triammonium arenium species, could not be achieved. Quantum chemical calculations are employed to enable full vibrational assignment as well to quantify charge localization. Triprotonation of 1,3,5‐tricyanobenzene and 1,3,5‐triaminobenzene was achieved in (super)acidic media. The nitrile species was also successfully trimethylated. Characterization of and comparison between the three trications have been carried out by vibrational and NMR spectroscopy as well as by single‐crystal X‐ray diffraction. The influence of protonation or methylation on the systems is evaluated and compared to predictions made by quantum‐chemical calculations. Abstract Protonation of 1,3,5‐tricyano‐ and 1,3,5‐triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective trinitrilium and triammonium species. Furthermore, the respective N‐methyl nitrilium species was synthesized by methylation. Characterization was performed by NMR and vibrational spectroscopy, followed by single‐crystal X‐ray diffraction analyses of selected species. Fourfold protonation of the amine, which would have led to the triammonium arenium species, could not be achieved. Quantum chemical calculations are employed to enable full vibrational assignment as well to quantify charge localization. Protonation of 1,3,5-tricyano- and 1,3,5-triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective trinitrilium and triammonium species. Furthermore, the respective N-methyl nitrilium species was synthesized by methylation. Characterization was performed by NMR and vibrational spectroscopy, followed by single-crystal X-ray diffraction analyses of selected species. Fourfold protonation of the amine, which would have led to the triammonium arenium species, could not be achieved. Quantum chemical calculations are employed to enable full vibrational assignment as well to quantify charge localization. Protonation of 1,3,5‐tricyano‐ and 1,3,5‐triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective trinitrilium and triammonium species. Furthermore, the respective N ‐methyl nitrilium species was synthesized by methylation. Characterization was performed by NMR and vibrational spectroscopy, followed by single‐crystal X‐ray diffraction analyses of selected species. Fourfold protonation of the amine, which would have led to the triammonium arenium species, could not be achieved. Quantum chemical calculations are employed to enable full vibrational assignment as well to quantify charge localization. Triprotonation of 1,3,5‐tricyanobenzene and 1,3,5‐triaminobenzene was achieved in (super)acidic media. The nitrile species was also successfully trimethylated. Characterization of and comparison between the three trications have been carried out by vibrational and NMR spectroscopy as well as by single‐crystal X‐ray diffraction. The influence of protonation or methylation on the systems is evaluated and compared to predictions made by quantum‐chemical calculations. Protonation of 1,3,5‐tricyano‐ and 1,3,5‐triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective trinitrilium and triammonium species. Furthermore, the respective N ‐methyl nitrilium species was synthesized by methylation. Characterization was performed by NMR and vibrational spectroscopy, followed by single‐crystal X‐ray diffraction analyses of selected species. Fourfold protonation of the amine, which would have led to the triammonium arenium species, could not be achieved. Quantum chemical calculations are employed to enable full vibrational assignment as well to quantify charge localization.
Author	Kornath, Andreas J. Nitzer, Alexander Hübsch, Robert Jessen, Christoph
AuthorAffiliation	1 Department of Chemistry and Pharmacy LMU Munich Butenandtstrasse 5–13 81377 Munich Germany
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Snippet	Protonation of 1,3,5‐tricyano‐ and 1,3,5‐triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective trinitrilium... Protonation of 1,3,5-tricyano- and 1,3,5-triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective trinitrilium... Abstract Protonation of 1,3,5‐tricyano‐ and 1,3,5‐triaminobenzene was achieved in various superacidic media, resulting in the formation of the respective...
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SubjectTerms	Crystal structure Equilibrium Fluorides Nitrogen NMR Nuclear magnetic resonance Protonation Quantum chemistry Solvents spectroscopy Sulfur superacid triaminobenzene trication tricyanobenzene
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Title	Two Roomtemperature‐stable Trications – Triprotonated Triamino‐ and Tricyanobenzene
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