TY - JOUR
T1 - Synthesis and reactivity of (benzoxazol-2-ylmethyl)phosphonic acid
AU - Pailloux, Sylvie
AU - Shirima, Cornel Edicome
AU - Smith, Karen Ann
AU - Duesler, Eileen N.
AU - Paine, Robert T.
AU - Williams, Neil J.
AU - Hancock, Robert D.
PY - 2010/10/18
Y1 - 2010/10/18
N2 - 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.
AB - 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.
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U2 - 10.1021/ic101079b
DO - 10.1021/ic101079b
M3 - Article
C2 - 20863097
AN - SCOPUS:78549278145
SN - 0020-1669
VL - 49
SP - 9369
EP - 9379
JO - Inorganic chemistry
JF - Inorganic chemistry
IS - 20
ER -