(Pyrrole-2,5-Diyl)-Bis(Nitronyl Nitroxide) and-Bis(Iminonitroxide): Specific Features of the Synthesis, Structure, and Magnetic Properties

(Pyrrole-2,5-Diyl)-Bis(Nitronyl Nitroxide) and-Bis(Iminonitroxide): Specific Features of the Synthesis, Structure, and Magnetic Properties Full article

Journal

Molecules
, E-ISSN: 1420-3049

Output data

Year: 2020, Volume: 25, Number: 7, Article number : 1503, Pages count : DOI: 10.3390/molecules25071503

Tags

nitronyl nitroxides; iminonitroxides; diradicals; pyrrole derivatives; magnetochemistry; quantum-chemical calculations

Authors

Tretyakov Evgeny ¹ , Tkacheva Anastasia ² , Romanenko Galina ² , Bogomyakov Artem ² , Stass Dmitri ^3,4 , Maryasov Alexander ¹ , Zueva Ekaterina ^5,6 , Trofimov Boris ⁷ , Ovcharenko Victor ²

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, 9 Ac Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Siberian Branch, Int Tomog Ctr, 3a Inst Skaya Str, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, VV Voevodsky Inst Chem Kinet & Combust, 3 Inst Skaya Str, Novosibirsk 630090, Russia
4	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia
5	(Данные Web of science) Kazan Natl Res Technol Univ, 68 Karl Marx Str, Kazan 420015, Russia
6	(Данные Web of science) Kazan Fed Univ, 18 Kremlyovskaya Str, Kazan 420008, Russia
7	(Данные Web of science) Russian Acad Sci, Siberian Branch, AE Favorsky Inst Chem, 1 Favorsky Str, Irkutsk 664033, Russia

In contrast to diradicals connected by alternant hydrocarbons, only a few studies have addressed diradicals connected by nonalternant hydrocarbons and their heteroatom derivatives. Here, the synthesis, structure, and magnetic properties of pyrrole-2,5-diyl-linked bis(nitronyl nitroxide) and bis(iminonitroxide) diradicals are described. The diradicals show characteristic electron spin resonance spectra in dilute glassy solutions, from which conclusions about the presence of distinct conformations, their symmetry, and interspin distance were made. X-ray diffraction analysis of the diradicals revealed that paramagnetic moieties lie in the plane of the pyrrole ring, because of the formation of an intramolecular hydrogen bond, O-NO...H-N, with O...H distances of 2.15-2.23 angstrom. The N-O groups participating in the formation of H-bonds have greater bond lengths (1.29 angstrom) as compared with nonparticipating groups (1.27 angstrom). The nitronyl nitroxide and iminonitroxide diradicals showed an intramolecular antiferromagnetic interaction, with J = -77.3 and -22.2 cm(-1), respectively (H = -2JS(1).S-2).

Tretyakov E. , Tkacheva A. , Romanenko G. , Bogomyakov A. , Stass D. , Maryasov A. , Zueva E. , Trofimov B. , Ovcharenko V.
(Pyrrole-2,5-Diyl)-Bis(Nitronyl Nitroxide) and-Bis(Iminonitroxide): Specific Features of the Synthesis, Structure, and Magnetic Properties

Molecules. 2020. V.25. N7. 1503 . DOI: 10.3390/molecules25071503 WOS Scopus РИНЦ

Full text from publisher

Published online:

Mar 26, 2020

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