Chiral hybrid aza-oxa-terpene-based macrocycles as selective extractants for Pd(II) and Au(III)

Chiral hybrid aza-oxa-terpene-based macrocycles as selective extractants for Pd(II) and Au(III) Научная публикация

Журнал

Tetrahedron
ISSN: 0040-4020

Вых. Данные

Год: 2024, Том: 156, Номер статьи : 133921, Страниц : 15 DOI: 10.1016/j.tet.2024.133921

Ключевые слова

Bis(α-amine oximes) · Macrocycles · Noble metals ·Selective extraction · Terpenoids

Авторы

Tkachev Alexey V. ¹ , Agafontsev Alexander M. ¹ , Zubricheva Darya V. ¹ , Bagryanskaya Irina Yu ¹ , Tikhova Vera D. ¹

Организации

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, 9 Academician Lavrentiev Ave., 630090 Novosibirsk, Russian Federation

Информация о финансировании (1)

Российский Научный Фонд
Министерство науки и инновационной политики Новосибирской области

23-23-10043

A series of novel hybride chiral macrocyclic compounds is described. The macrocyclic core of the new compounds is decorated with monoterpene fragments and includes 2 imine nitrogens and 2 tertiary amine nitrogens of the N,N-piperazine linkage as well as several repeating ethyleneoxy units resembling those of crown ethers. The macrocyclic compounds are prepared in moderate preparative yield (16–31%) upon treatment of a mixture of bis(α-amine oximes) and α,ω-dichloro derivatives of tri-, tetra- and hexa-ethylene glycol with sodium methylsulfinylmethylide. Chemical structure of the new macrocycles was established by a complex of spectroscopic techniques and X-ray analysis. The new macrocyclic compounds demonstrate remarkable selectivity with respect to Pd(II) and Au(III) and are able to efficiently extract these metals from acidic media containing a complex mixture of alkali metals, 3d-elements and noble metals. The features of conformational behavior, the ability to form complexes and the selectivity of extraction were studied using quantum chemical calculations at the DFT level. Based on the data obtained, a consistent scheme has been formulated to explain the features of extraction and the extraction selectivity of individual macrocycles.

Tkachev A.V. , Agafontsev A.M. , Zubricheva D.V. , Bagryanskaya I.Y. , Tikhova V.D.
Chiral hybrid aza-oxa-terpene-based macrocycles as selective extractants for Pd(II) and Au(III)
Tetrahedron. 2024. V.156. 133921 :1-15. DOI: 10.1016/j.tet.2024.133921 Scopus

Поступила в редакцию:	18 дек. 2023 г.
Принята к публикации:	29 февр. 2024 г.
Опубликована online:	8 мар. 2024 г.
Опубликована в печати:	28 апр. 2024 г.

Scopus	2-s2.0-85187994452
OpenAlex	W4392626960