Fluorinated diaminobicyclooxacalixarene and diaminotetraoxacalixarenes: Synthesis and conformational behaviour

Fluorinated diaminobicyclooxacalixarene and diaminotetraoxacalixarenes: Synthesis and conformational behaviour Научная публикация

Журнал

Journal of Fluorine Chemistry
ISSN: 0022-1139

Вых. Данные

Год: 2024, Том: 273, Страницы: 110235 Страниц : 1 DOI: 10.1016/j.jfluchem.2023.110235

Ключевые слова

Fluorinated diaminotetraoxacalixarenes; Diaminobicycloxacalixarenes; Pentafluoronitrobenzene; Orcinol; Conformational equilibrium; X-ray diffraction; Complexation

Авторы

Han Huizhe ^1,2 , Kovtonyuk Vladimir N. ¹ , Gatilov Yurii V. ¹ , Andreev Rodion V. ¹ , Nefedov Andrey A. ^1,2

Организации

1	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Novosibirsk 630090, Russia
2	Novosibirsk National Research State University, Novosibirsk 630090, Russia

Highlights • Fluorinated diaminooxacalixarenes are formed by the reaction of the corresponding dinitrooxacalixarenes with sodium dithionite. • Tetraoxacalix[4]arenes with nitro and amino groups in the inner rim exist in solution as an equilibrium mixture of conformers with 1,3-alternate and "chair" structure. • For fluorinated tetraoxacalixarenes with amino groups in the inner rim, the 1,3-alternate structure is more preferable to the "chair" structure. • The position of conformational equilibrium of tetraoxacalixarenes with nitro groups in the inner rim depends on the polarity of the solvent. Abstract Polyfluorinated diaminotetraoxacalixarenes and diaminobicyclooxacalixarene were obtained in good yield by reduction of the corresponding dinitrooxacalixarenes with sodium dithionite. Fluorinated tetraoxacalix[4]arenes with nitro and amino groups located in the inner rim of the macrocycle exists in the solution as an equilibrium mixture of two conformers. For diaminotetraoxacalixarenes the conformational equilibrium is shifted towards conformers having a 1,3-alternate structure. The ESI-MS method shows the possibility of complexing fluorinated diaminotetraoxacalixarenes and diaminobicyclooxacalixarenes with metal cations.

Han H. , Kovtonyuk V.N. , Gatilov Y.V. , Andreev R.V. , Nefedov A.A.
Fluorinated diaminobicyclooxacalixarene and diaminotetraoxacalixarenes: Synthesis and conformational behaviour
Journal of Fluorine Chemistry. 2024. V.273. P.110235. DOI: 10.1016/j.jfluchem.2023.110235 WOS

Поступила в редакцию:	19 окт. 2023 г.
Принята к публикации:	30 нояб. 2023 г.
Опубликована online:	7 дек. 2023 г.
Опубликована в печати:	1 янв. 2024 г.

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