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

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.

Tretyakov, E Tkacheva, A Romanenko, G Bogomyakov, A Stass, D Maryasov, A Zueva, E Trofimov, B Ovcharenko, V

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Publisher:: MDPI
Publication Type:: Journal Article
Citation:: Molecules (Basel, Switzerland), 2020, 25, (7)
Issue Date:: 2020-03-26

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Field	Value	Language
dc.contributor.author	Tretyakov, E
dc.contributor.author	Tkacheva, A
dc.contributor.author	Romanenko, G
dc.contributor.author	Bogomyakov, A
dc.contributor.author	Stass, D
dc.contributor.author	Maryasov, A
dc.contributor.author	Zueva, E
dc.contributor.author	Trofimov, B
dc.contributor.author	Ovcharenko, V
dc.date.accessioned	2020-12-12T04:39:18Z
dc.date.available	2020-03-25
dc.date.available	2020-12-12T04:39:18Z
dc.date.issued	2020-03-26
dc.identifier.citation	Molecules (Basel, Switzerland), 2020, 25, (7)
dc.identifier.issn	1420-3049
dc.identifier.issn	1420-3049
dc.identifier.uri	http://hdl.handle.net/10453/144642
dc.description.abstract	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, ONO…HN, with O…H distances of 2.15-2.23 Å. The N-O groups participating in the formation of H-bonds have greater bond lengths (~1.29 Å) as compared with nonparticipating groups (~1.27 Å). The nitronyl nitroxide and iminonitroxide diradicals showed an intramolecular antiferromagnetic interaction, with J = -77.3 and -22.2 cm-1, respectively (H = -2JS1S2).
dc.format	Electronic
dc.language	eng
dc.publisher	MDPI
dc.relation.ispartof	Molecules (Basel, Switzerland)
dc.relation.isbasedon	10.3390/molecules25071503
dc.rights	info:eu-repo/semantics/openAccess
dc.subject	0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, 0307 Theoretical and Computational Chemistry
dc.subject.classification	Organic Chemistry
dc.title	(Pyrrole-2,5-Diyl)-Bis(Nitronyl Nitroxide) and-Bis(Iminonitroxide): Specific Features of the Synthesis, Structure, and Magnetic Properties.
dc.type	Journal Article
utslib.citation.volume	25
utslib.location.activity	Switzerland
utslib.for	0304 Medicinal and Biomolecular Chemistry
utslib.for	0305 Organic Chemistry
utslib.for	0307 Theoretical and Computational Chemistry
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney
utslib.copyright.status	open_access	*
dc.date.updated	2020-12-12T04:39:08Z
pubs.issue	7
pubs.publication-status	Published
pubs.volume	25
utslib.citation.issue	7

Abstract:

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, ONO…HN, with O…H distances of 2.15-2.23 Å. The N-O groups participating in the formation of H-bonds have greater bond lengths (~1.29 Å) as compared with nonparticipating groups (~1.27 Å). The nitronyl nitroxide and iminonitroxide diradicals showed an intramolecular antiferromagnetic interaction, with J = -77.3 and -22.2 cm-1, respectively (H = -2JS1S2).

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http://hdl.handle.net/10453/144642