Nitro Derivatives of Benzoazacrown Ethers: Synthesis, Structure, and Complexation with Metal and Ammonium Cations and Fluoride Anionстатья
Статья опубликована в журнале из списка RSCI Web of Science
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Статья опубликована в журнале из перечня ВАК
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 1 августа 2019 г.
Аннотация:A method was developed for the synthesis of nitrobenzoazacrown ethers by N-demethylation of N-methylnitrobenzoazacrown ethers on treatment with ammonium iodide, resulting in the formation of benzoazacrown ethers in 95–100 % yields. The spatial structure of nitrobenzoazacrown ethers and their complexation behaviour towards alkali and alkaline-earth metal cations, ammonium ions, and fluoride anions were investigated using X-ray diffraction and 1H NMR spectroscopy. It was shown that the stability of host–guest type complexes of nitrobenzoazacrown ethers
with metal and ammonium cations in MeCN-d3 is lower than the stability of complexes formed by N-alkyl-substituted analogues with the same macrocycle size. It was shown that fluoride anions in DMSO-d6 or MeCN-d3 can bind to nitrobenzoazacrown ethers via hydrogen bonding with the NH group of the macrocycle.