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

doi:10.1021/ic101079b

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

4 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 (pK_a) 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 language	English (US)
Pages (from-to)	9369-9379
Number of pages	11
Journal	Inorganic Chemistry
Volume	49
Issue number	20
DOIs	https://doi.org/10.1021/ic101079b
State	Published - Oct 18 2010

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title = "Synthesis and reactivity of (benzoxazol-2-ylmethyl)phosphonic acid",

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.",

author = "Sylvie Pailloux and Shirima, \{Cornel Edicome\} and Smith, \{Karen Ann\} and Duesler, \{Eileen N.\} and Paine, \{Robert T.\} and Williams, \{Neil J.\} and Hancock, \{Robert D.\}",

year = "2010",

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doi = "10.1021/ic101079b",

language = "English (US)",

volume = "49",

pages = "9369--9379",

journal = "Inorganic Chemistry",

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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.

UR - https://www.scopus.com/pages/publications/78549278145

UR - https://www.scopus.com/pages/publications/78549278145#tab=citedBy

U2 - 10.1021/ic101079b

DO - 10.1021/ic101079b

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EP - 9379

JO - Inorganic Chemistry

JF - Inorganic Chemistry

IS - 20

ER -

Synthesis and reactivity of (benzoxazol-2-ylmethyl)phosphonic acid

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