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1,10‐Diaza‐18‐crown‐ether, Modified by Phosphonate Pendant Arms – Synthesis, Structure, and Picrate Extraction Properties
Author(s) -
Khusainova Narkis G.,
Rybakov Sergey M.,
Safin Damir A.,
Krivolapov Dmitriy B.,
Litvinov Igor A.
Publication year - 2008
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200800202
Subject(s) - picrate , phosphonate , chemistry , crown ether , extraction (chemistry) , ether , crystal structure , derivative (finance) , crystallography , calixarene , stereochemistry , polymer chemistry , organic chemistry , molecule , ion , financial economics , economics
Reaction of O,O′ ‐diisopropyl‐3‐methyl‐1,2‐butadienylphosphonate with 1,10‐diaza‐18‐crown‐6 in the presence of a catalytic amount of i PrONa leads to the new crown‐ether derivative, containing phosphonate pendant arms ( L ). The structure of the compound obtained was investigated by single crystal X‐ray diffraction analysis, IR, 1 H and 31 P{ 1 H} NMR spectroscopy, and microanalysis. In the crystal structure the side arms of L are in an anti disposition relative to the macrocyclic cavity. It was established that phosphorylation of 1,10‐diaza‐18‐crown‐6 by allenylphosphonate results in an increase of extraction of NaPic and KPic, whereas LiPic and NH 4 Pic are extracted practically in the same level.