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Synthesis and Reactivity of (benzoxazol-2-ylmethyl)phosphonic Acid

Synthesis and Reactivity of (benzoxazol-2-ylmethyl)phosphonic Acid

Sylvie Pailloux, Cornel Edicome Shirima, Karen Ann Smith, Eileen N Duesler, Robert T Paine, Neil J Williams, Robert D Hancock

Inorg Chem. 2010 Oct 18;49(20):9369-79.

PMID: 20863097

Abstract:

An efficient three step synthesis of (benzoxazol-2-ylmethyl)phosphonic acid (6-H(2)) is described along with IR, mass spectrometry (MS), and (1)H, (13)C, and (31)P NMR spectroscopic characterization data, and a single crystal X-ray diffraction structure determination. 6-H(2) is unstable in acidic aqueous solutions (pH < 4) undergoing ring-opening to give [(2-hydroxyphenylcarbamoyl)methyl] phosphonic acid (7-H(2)) that is characterized by IR, MS, and NMR methods. The protonation constants (pK(a)) for 7-H(2) have been measured, and crystal structure determinations for (NH(4))(7-H) and K(7-H)·DMF are described. Reactions of NaOH and KOH with 6-H(2) in MeOH/H(2)O solutions led to isolation and crystal structure determinations of the salts [Na(6-H)·H(2)O](2), K(6-H), Na(3)(6)(6-H)·H(2)O, and [K(2)(6)](2)·3H(2)O. The complexation reactions of 7-H(2) with La(III), Nd(III), and Gd(III), as a function of pH, were also examined by titrametric methods, and a model for the 1:1 anion binding with Ln(III) cations is proposed.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
CS353745	(2-Hydroxyethyl-d4)phosphonic acid			Price

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