Aqua complex of iron(III) and 5-chloro-3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-2-hydroxybenzenesulfonate: Structure and catalytic activity in Henry reaction

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• 作者：Kamran T. Mahmudov ; Maximilian N. Kopylovich ; Matti Haukka ; Gunay S. Mahmudova ; Esp ; i F. Esmaeila ; Famil M. Chyragov ; Arm ; o J.L. Pombeiro
• 关键词：Arylhydrazone of 5 ; 5-dimethylcyclohexane-1 ; 3-dione ; Water-soluble iron(III) complex ; Halogen bonding ; Henry reaction
• 刊名：Journal of Molecular Structure
• 出版年：2013
• 出版时间：24 September, 2013
• 年：2013
• 卷：1048
• 期：Complete
• 页码：108-112
• 全文大小：1077 K

文摘

A water-soluble iron(III) complex [Fe(H₂O)₃(L)]¡¤5H₂O (1) was prepared by reaction of iron(III) chloride with 5-chloro-3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-2-hydroxy-benzenesulfonic acid (H₃L). The complex was characterized by IR, ¹H NMR and ESI-MS spectroscopies, elemental and X-ray crystal structural analyses. The coordination environment of the central iron(III) is a distorted octahedron, three sites being occupied by L^3? ligand, which chelates in O,N,O fashion, while three other sites are filled with the water molecules. The uncoordinated water molecules are held in the channels of the overall 3D supramolecular structure by the carbonyl and sulfonyl groups of L^3? and the ligated waters. Apart from the multiple hydrogen bonds, an intermolecular charge-assisted O¡¤¡¤¡¤Cl halogen bonding with 3.044 ? distance was described. 1 acts as an effective catalyst in the Henry reaction producing nitroaldols from nitroethane and various aldehydes with yields up to 90 % and threo/erythro diastereoselectivity ranging from 3:1 to 1:1.