172164-49-7Relevant academic research and scientific papers
N-Methylbenzoazacrown ethers with the nitrogen atom conjugated with the benzene ring: The improved synthesis and the reasons for the high stability of complexes with metal and ammonium cations
Gromov, Sergey P.,Dmitrieva, Svetlana N.,Vedernikov, Artem I.,Kurchavov, Nikolay A.,Kuz'Mina, Lyudmila G.,Strelenko, Yuri A.,Alfimov, Michael V.,Howard, Judith A. K.
body text, p. 823 - 833 (2010/06/16)
An improved method for the synthesis of formyl derivatives of N - Methylbenzoazacrown ethers is proposed. They are prepared in up to 68% yields over fewer steps and with a much shorter time required for the last step. The stability constants of complexes formed by N-methylbenzoazacrown ethers and their structural analogs with alkali metal, alkaline - Earth metal and ammonium cations were determined by 1H NMR titration in CD3CN. High stability of complexes of N-methyl derivatives of benzoazacrown ethers is demonstrated, comparable with or even exceeding the stability of benzocrown-ether complexes and markedly exceeding the stability of complexes of phenylazacrown ethers with the same macrocycle size. The structures of azacrown ethers and their complexes with Ba(ClO4)2 were studied by X-ray diffraction. A high degree of pre-organization of N - Methylbenzoazacrown ethers toward the formation of complexes with metal and ammonium cations was noted, which is due to the clear-cut pyramidal geometry of the nitrogen atom and the orientation of the lone electron pairs (LEPs) of most heteroatoms towards the centre of the macroheterocycle. Copyright
Novel promising benzoazacrown ethers as a result of ring transformation of benzocrown ethers: Synthesis, structure, and complexation with Ca2+
Gromov, Sergey P.,Dmitrieva, Svetlana N.,Vedernikov, Artem I.,Kuz'Mina, Lyudmila G.,Churakov, Andrey V.,Strelenko, Yuri A.,Howard, Judith A. K.
, p. 3189 - 3199 (2007/10/03)
A series of promising benzoazacrown ethers with the nitrogen atom conjugated with the benzene ring were synthesized using a novel synthetic procedure based on stepwise transformation of the macroheterocycle. The structures and spectral properties of the r
Macrocycle opening in crown ethers 2. Template effect in macrocycle opening in formyl derivatives of benzocrown ethers under the action of amines with the formation of podands
Gromov,Vedernikov,Fedorova
, p. 648 - 653 (2007/10/03)
Macrocycle opening in derivatives of benzocrown ethers under the action of amines is affected by the nature of the heteroatoms in the macrocycle, the nature of the functional group in the benzene ring of the crown ether, and the length, branching, and num
Macrocycle opening in formyl derivatives of benzocrown ethers under the action of methylamine
Gromov, N. N.,Vedernikov, A. I.,Fedorova, O. A.
, p. 923 - 926 (2007/10/02)
A new method for synthesizing nitrogen-containing podands by nucleophilic regioselective cleavage of the macrocycle in formyl derivatives of benzocrown ethers by heating with methylamine and methylammonium chloride has been developed.This reaction is the
