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2,6-Dimethylphenol derived H-phosphonate and alpha-hydroxyphosphonate: facile synthesis, crystal chemistry, supramolecular association and metal complexation

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Title 2,6-Dimethylphenol derived H-phosphonate and alpha-hydroxyphosphonate: facile synthesis, crystal chemistry, supramolecular association and metal complexation
 
Creator HOSSAIN, S
GUPTA, SK
MURUGAVEL, R
 
Subject HYDROXY PHOSPHONATES
UNACTIVATED KETONES
PROTON CONDUCTIVITY
AMIDO COMPLEXES
ENANTIOSELECTIVE SYNTHESIS
COORDINATION POLYMER
EFFICIENT SYNTHESIS
CATALYTIC-ACTIVITY
ORGANIC FRAMEWORK
ACIDIC CONDITIONS
 
Description Facile synthesis of a H-phosphonate [(ArO)P(O)H(OH)] (2) and an alpha-hydroxyarylphosphonate [(ArO)P(O)(OH)(CMe2OH)] (3) has been achieved through the hydrolysis of [(ArO)PCl2] (1) with toluene and acetone as the solvent, respectively. The dichloride (1) itself was synthesized from the reaction of ArOH (Ar = 2,6-Me2C6H3O) with phosphorous trichloride. The unstable H-phosphonate (2) and the three different crystalline modifications of the alpha-hydroxyarylphosphonate (3) (viz., ansolvate, solvate and hydrate) have been crystallized under different crystallization conditions and their molecular structures have been determined by single crystal X-ray diffraction studies. These four crystalline forms exhibit either two-dimensional sheet-like polymeric structures or tubular structures with water channels, assisted by supramolecular interactions such as H-bonding, CH-pi, etc. Crystallisation of the alpha-hydroxyarylphosphonate (3) from a warm dimethylformamide solution leads to the ready decomposition of the solvent to the dimethylammonium cation, giving the salt of 3, [Me2NH2][(ArO)(CMe2OH)POO] (6). The reactivity of the alpha-hydroxyarylphosphonate 3 with metal acetates has been investigated and its copper and zinc complexes [M(HL)(2)(2,2'-bpy)(H2O)](H2O) (M = Cu (7); Zn (8) (HL = [(ArO) P(O)(O)(CMe2OH)](-)) have been isolated and structurally characterized. Mononuclear 7 and 8 form linear polymeric chains assisted by intermolecular H-bonding interactions involving a large number of proton donor and acceptor sites present in these complexes.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2016-01-15T07:02:46Z
2016-01-15T07:02:46Z
2015
 
Type Article
 
Identifier CRYSTENGCOMM, 17(23)4355-4366
1466-8033
http://dx.doi.org/10.1039/c5ce00675a
http://dspace.library.iitb.ac.in/jspui/handle/100/18000
 
Language en