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Self-assembly of iodoacetylenyl-substituted nitronyl nitroxides via halogen bonding Full article

Journal CrystEngComm
ISSN: 1466-8033
Output data Year: 2023, Volume: 25, Number: 44, Pages: 6152-6161 Pages count : 10 DOI: 10.1039/d3ce00735a
Authors Shurikov Matvey K. 1 , Tretyakov Evgeny V. 2 , Petunin Pavel V. 1 , Votkina Darya E. 1 , Romanenko Galina 3 , Bogomyakov Artem 3 , Piña Sergi Burguera 4 , Frontera Antonio 4 , Kukushkin Vadim Yu. 5 , Postnikov Pavel S 1
Affiliations
1 Research School of Chemistry & Applied Biomedical Sciences, Tomsk Polytechnic University, Lenin Av. 30, Tomsk 634050, Russian Federation
2 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Av. 47, Moscow 119991, Russian Federation
3 International Tomography Center, Siberian Branch of Russian Academy of Sciences, Institutskaya Str. 3a, Novosibirsk 630090, Russian Federation
4 Departament de Química, Universitat de les Illes Balears, Crta de Valldemossa km 7.5, 07122 Palma de Mallorca, Baleares, Spain
5 Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, Saint Petersburg 199034, Russian Federation

Abstract: Novel nitronyl nitroxides, namely 2-(3-iodoethynylphenyl)- and 2-(4-iodoethynylphenyl)-4,4,5,5-tetramethyl-imidazoline-3-oxyl-1-oxides, were prepared by condensation of appropriate aldehydes with 2,3-bis(hydroxylamino)-2,3-dimethylbutane followed by oxidative treatment with NaIO4. Crystal and molecular structures of the obtained paramagnets were studied by single-crystal X-ray diffraction. In the crystals, the radicals are assembled into zigzag chains in which the radical building blocks are linked by intermolecular I⋯N–O halogen bonding. Magnetic analyses revealed that in both nitronyl nitroxides, the radicals are weakly coupled. Nonetheless, spin–spin interactions in the 3-iodoethynyl isomer are antiferromagnetic, and the coupling is stronger than that in the 4-iodoethynyl derivative, in which the exchange interaction is ferromagnetic. DFT calculations in combination with MEP, NCIplot, and QTAIM analyses were used to evaluate and characterize the structure-directing halogen bonding interactions observed in the solid state of both compounds.
Cite: Shurikov M.K. , Tretyakov E.V. , Petunin P.V. , Votkina D.E. , Romanenko G. , Bogomyakov A. , Piña S.B. , Frontera A. , Kukushkin V.Y. , Postnikov P.S.
Self-assembly of iodoacetylenyl-substituted nitronyl nitroxides via halogen bonding
CrystEngComm. 2023. V.25. N44. P.6152-6161. DOI: 10.1039/d3ce00735a WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:001089683900001
Scopus: 2-s2.0-85175578860
OpenAlex: W4387790541
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