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

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

An efficient three step synthesis of (benzoxazol-2-ylmethyl)phosphonic acid (6-H2) is described along with IR, mass spectrometry (MS), and 1H, 13C, and 31P NMR spectroscopic characterization data, and a single crystal X-ray diffraction structure determination. 6-H2 is unstable in acidic aqueous solutions (pH < 4) undergoing ring-opening to give [(2-hydroxyphenylcarbamoyl)methyl] phosphonic acid (7-H2) that is characterized by IR, MS, and NMR methods. The protonation constants (pKa) for 7-H2 have been measured, and crystal structure determinations for (NH4)(7-H) and K(7-H) · DMF are described. Reactions of NaOH and KOH with 6-H2 in MeOH/H2O solutions led to isolation and crystal structure determinations of the salts [Na(6-H) · H2O]2, K(6-H), Na3(6)(6-H) · H2O, and [K 2(6)]2 · 3H2O. The complexation reactions of 7-H2 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.

Original languageEnglish (US)
Pages (from-to)9369-9379
Number of pages11
JournalInorganic Chemistry
Volume49
Issue number20
DOIs
StatePublished - Oct 18 2010

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