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One, two, and three methylene phosphonic acid groups (-CH(2)PO(3)H(2)) on a mesitylene ring: synthesis, characterization and aspects of supramolecular aggregation

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Title One, two, and three methylene phosphonic acid groups (-CH(2)PO(3)H(2)) on a mesitylene ring: synthesis, characterization and aspects of supramolecular aggregation
 
Creator MURUGAVEL, R
SINGH, MP
 
Subject metal-organic framework
trimesic acid
crystal-structures
solid-state
chemistry
clusters
complexes
ligands
organophosphonate
coordination
 
Description The ease of substitution of -CH(2)Br group on the mesitylene ring in a stepwise manner has been exploited to prepare mesitylene mono-, bis-, and tris-methylene phosphonic acids C(6)H(2)Me(3)(CH(2)PO(3)H(2)) (1), C(6)HMe(3)(CH(2)PO(3)H(2))(2) (2), and C(6)Me(3)(CH(2)PO(3)H(2))(3) (3) in 80-90% yield, through a Michaelis-Arbuzov reaction followed by acid hydrolysis. Compounds 1-4 have been characterized by analytical and spectroscopic (IR, NMR, and MS) techniques. The X-ray structural investigations on all the three compounds reveal that the central mesitylene ring is a robust platform for hosting multiple methylene phosphonic acid groups. Mesitylene mono-methylene phosphonic acid 1, which can be considered as the sterically encumbered modification of benzyl phosphonic acid, interestingly associates as a one-dimensional tubular structure through extensive O-H center dot center dot center dot O hydrogen bonding between adjacent -PO(3)H(2) groups, albeit with no such interactions between the tubes due to the highly hydrophobic nature of the surface. The X-ray structure of mesitylene-1,3-diphosphonic acid 2 reveals that the molecules exhibit a syn-orientation of the -CH(2)PO(3)H(2), which are involved in extensive P-OH center dot center dot center dot O hydrogen bonding to result in a two-dimensional layered structure. The presence of three -PO(3)H(2) units on the same side of the mesitylene ring in 3 results in a three-dimensional framework solid. The present studies clearly reveal a linear relationship between the dimensionality of the supramolecular structure and the number of phosphonic acid moieties on the mesitylene ring.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2011-08-28T15:13:29Z
2011-12-26T12:58:05Z
2011-12-27T05:47:18Z
2011-08-28T15:13:29Z
2011-12-26T12:58:05Z
2011-12-27T05:47:18Z
2010
 
Type Article
 
Identifier NEW JOURNAL OF CHEMISTRY, 34(9), 1846-1854
1144-0546
http://dx.doi.org/10.1039/b9nj00691e
http://dspace.library.iitb.ac.in/xmlui/handle/10054/11770
http://hdl.handle.net/10054/11770
 
Language en