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ISSN 1998-9539

Nitro Derivatives of Benzoazacrown Ethers: Synthesis, Structure, and Complexation with Metal and Ammonium Cations and Fluoride Anion

Svetlana N. Dmitrieva,a Nikolay A. Kurchavov,a Lyudmila G. Kuz’mina,b Artem I. Vedernikov,a Marina V. Churakova,a Sergey K. Sazonov,a Judith A. K. Howard,cand Sergey P. Gromova,d@

aPhotochemistry Center of RAS, FSRC “Crystallography and Photonics”, Russian Academy of Sciences, 119421 Moscow, Russian Federation

bN.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation

cChemistry Department, Durham University, DH1 3LE Durham, UK

dDepartment of Chemistry, M.V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation

@Corresponding author E-mail: spgromov@mail.ru

 

DOI: 10.6060/mhc181218g

 

A method was developed for the synthesis of nitrobenzoazacrown ethers by N-demethylation of N-methyl-nitrobenzoazacrown 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-d3is 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.

 

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