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Investigation of cation complexation behavior of azacrown ether substituted benzochromene
Author(s) -
Fedorova O. A.,
Maurel F.,
Chebun'kova A. V.,
Strokach Yu. P.,
Valova T. M.,
Kuzmina L. G.,
Howard J. A. K.,
Wenzel M.,
Gloe K.,
Lokshin V.,
Samat A.
Publication year - 2007
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1181
Subject(s) - chemistry , acetonitrile , crown ether , ether , divalent , alkali metal , selectivity , inorganic chemistry , solvent , organic chemistry , ion , catalysis
The study of the complex formation of 3,3‐diphenyl‐3 H ‐benzo[f]chromenes containing aza‐18‐crown‐6‐ether, diaza‐18‐crown‐6‐ether or morpholine units with alkali, alkaline earth, heavy and transition metal cations in acetonitrile is reported. The spectroscopic and kinetic behavior of the photomerocyanine isomers of these chromenes is strongly affected by complexation with a metal cation. In order to interpret some of experimental data, an ab initio theoretical analysis of photochromic‐crown ether and its cation complexes was conducted. The different site of coordination of mono‐ and divalent cations to determine the minimum‐energy structure of benzochromene complexes in gas phase as well as in acetonitrile as solvent was explored. The coordination of both carbonyl oxygen and crown‐ether macrocyle with divalent cations in carbonyl‐capped structure is found to be the most stable isomer in gas as well as in condensed media. The crown‐containing benzochromenes were studied in liquid‐liquid extraction experiments toward there capacity to transfer metallic salts from water into an organic phase.The high selectivity to extraction of Ag + was found. Copyright © 2007 John Wiley & Sons, Ltd.