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Reaction of the template synthesis of the boron-capped iron(II) macrobicyclic complexes (clathrochelates) of a general formula FeD3(BR)2 (where D2– is the alicyclic α-dioximate dianion, R is the apical substituent) are known to be the unique objects for studying of the kinetics of their coordination-driven self-assembly from three chelating and two cross-linking ligand synthones on the iron(II) ion as a matrix. We performed these reactions for the methylboron-capped iron(II) clathrochelates — the derivatives of alicyclic six-, seven- and eight-membered α-dioximes. Their ring size was found to dramatically affect the kinetic schemes and parameters of the template synthesis and acidic decomposition reactions of these clathrochelates.