Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl) phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH) (Ph)

Manab Chakravarty, Sylvie L Pailloux, S. Ouizem, K. A. Smith, Eileen N. Duesler, Robert T. Paine, Neil J. Williams, Robert D. Hancock

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Abstract

A three-step synthesis for the bifunctional ligand (phenyl)(pyridin-2- ylmethyl)phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH)(Ph) (3-H), was developed. The molecule was characterized by spectroscopic methods, and single crystal X-ray diffraction analysis, and the molecule found to exist in a zwitterionic form (3′). Protonation constants for 3′ were measured spectrophotometrically in 0.1 M NaClO 4 aqueous solution. The coordination chemistry of 3′ toward CdCl 2 and PtCl 2 was explored, and the complexes [Cd(3′)Cl 2] 2 and [Pt(3 -) 2]·CHCl 3 were isolated and structurally characterized by single crystal X-ray diffraction methods. Complexation constants for 3′ with Cd(II), Zn(II) and La(III), as a function of pH, were measured by titration techniques. An initial effort to prepare the [pyridin-bis(2,6-yl-methylphosphinodithioic acid)] analog of 3-H led to the formation and isolation of (phenyl)(6- methylpyridin-2-ylmethyl)phosphinodithioic acid, [2-C 5H 3N(6-CH 3)]CH 2P(S)(SH)(Ph) (6-H), that was characterized by spectroscopic methods and single crystal X-ray diffraction analysis. As found with 3-H, 6-H, adopts a zwitterionic structural form (6′).

Original languageEnglish (US)
Pages (from-to)327-335
Number of pages9
JournalPolyhedron
Volume33
Issue number1
DOIs
StatePublished - Feb 9 2012

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Metals
Single crystals
methylidyne
chemistry
X ray diffraction analysis
acids
Acids
single crystals
synthesis
diffraction
metals
Molecules
x rays
Protonation
Complexation
Titration
titration
molecules
isolation
Ligands

Keywords

  • Cd(II)
  • Complexation constants
  • Dithiophosphinic acid
  • Protonation constants
  • Pt(II) complexes
  • Pyridyl
  • X-ray crystal structures

Cite this

Chakravarty, M., Pailloux, S. L., Ouizem, S., Smith, K. A., Duesler, E. N., Paine, R. T., ... Hancock, R. D. (2012). Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl) phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH) (Ph). Polyhedron, 33(1), 327-335. https://doi.org/10.1016/j.poly.2011.11.041

Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl) phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH) (Ph). / Chakravarty, Manab; Pailloux, Sylvie L; Ouizem, S.; Smith, K. A.; Duesler, Eileen N.; Paine, Robert T.; Williams, Neil J.; Hancock, Robert D.

In: Polyhedron, Vol. 33, No. 1, 09.02.2012, p. 327-335.

Research output: Contribution to journalArticle

Chakravarty, M, Pailloux, SL, Ouizem, S, Smith, KA, Duesler, EN, Paine, RT, Williams, NJ & Hancock, RD 2012, 'Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl) phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH) (Ph)', Polyhedron, vol. 33, no. 1, pp. 327-335. https://doi.org/10.1016/j.poly.2011.11.041
Chakravarty, Manab ; Pailloux, Sylvie L ; Ouizem, S. ; Smith, K. A. ; Duesler, Eileen N. ; Paine, Robert T. ; Williams, Neil J. ; Hancock, Robert D. / Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl) phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH) (Ph). In: Polyhedron. 2012 ; Vol. 33, No. 1. pp. 327-335.
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abstract = "A three-step synthesis for the bifunctional ligand (phenyl)(pyridin-2- ylmethyl)phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH)(Ph) (3-H), was developed. The molecule was characterized by spectroscopic methods, and single crystal X-ray diffraction analysis, and the molecule found to exist in a zwitterionic form (3′). Protonation constants for 3′ were measured spectrophotometrically in 0.1 M NaClO 4 aqueous solution. The coordination chemistry of 3′ toward CdCl 2 and PtCl 2 was explored, and the complexes [Cd(3′)Cl 2] 2 and [Pt(3 -) 2]·CHCl 3 were isolated and structurally characterized by single crystal X-ray diffraction methods. Complexation constants for 3′ with Cd(II), Zn(II) and La(III), as a function of pH, were measured by titration techniques. An initial effort to prepare the [pyridin-bis(2,6-yl-methylphosphinodithioic acid)] analog of 3-H led to the formation and isolation of (phenyl)(6- methylpyridin-2-ylmethyl)phosphinodithioic acid, [2-C 5H 3N(6-CH 3)]CH 2P(S)(SH)(Ph) (6-H), that was characterized by spectroscopic methods and single crystal X-ray diffraction analysis. As found with 3-H, 6-H, adopts a zwitterionic structural form (6′).",
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T1 - Synthesis and metal coordination chemistry of (phenyl)(pyridin-2-ylmethyl) phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH) (Ph)

AU - Chakravarty, Manab

AU - Pailloux, Sylvie L

AU - Ouizem, S.

AU - Smith, K. A.

AU - Duesler, Eileen N.

AU - Paine, Robert T.

AU - Williams, Neil J.

AU - Hancock, Robert D.

PY - 2012/2/9

Y1 - 2012/2/9

N2 - A three-step synthesis for the bifunctional ligand (phenyl)(pyridin-2- ylmethyl)phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH)(Ph) (3-H), was developed. The molecule was characterized by spectroscopic methods, and single crystal X-ray diffraction analysis, and the molecule found to exist in a zwitterionic form (3′). Protonation constants for 3′ were measured spectrophotometrically in 0.1 M NaClO 4 aqueous solution. The coordination chemistry of 3′ toward CdCl 2 and PtCl 2 was explored, and the complexes [Cd(3′)Cl 2] 2 and [Pt(3 -) 2]·CHCl 3 were isolated and structurally characterized by single crystal X-ray diffraction methods. Complexation constants for 3′ with Cd(II), Zn(II) and La(III), as a function of pH, were measured by titration techniques. An initial effort to prepare the [pyridin-bis(2,6-yl-methylphosphinodithioic acid)] analog of 3-H led to the formation and isolation of (phenyl)(6- methylpyridin-2-ylmethyl)phosphinodithioic acid, [2-C 5H 3N(6-CH 3)]CH 2P(S)(SH)(Ph) (6-H), that was characterized by spectroscopic methods and single crystal X-ray diffraction analysis. As found with 3-H, 6-H, adopts a zwitterionic structural form (6′).

AB - A three-step synthesis for the bifunctional ligand (phenyl)(pyridin-2- ylmethyl)phosphinodithioic acid, [2-C 5H 4N]CH 2P(S)(SH)(Ph) (3-H), was developed. The molecule was characterized by spectroscopic methods, and single crystal X-ray diffraction analysis, and the molecule found to exist in a zwitterionic form (3′). Protonation constants for 3′ were measured spectrophotometrically in 0.1 M NaClO 4 aqueous solution. The coordination chemistry of 3′ toward CdCl 2 and PtCl 2 was explored, and the complexes [Cd(3′)Cl 2] 2 and [Pt(3 -) 2]·CHCl 3 were isolated and structurally characterized by single crystal X-ray diffraction methods. Complexation constants for 3′ with Cd(II), Zn(II) and La(III), as a function of pH, were measured by titration techniques. An initial effort to prepare the [pyridin-bis(2,6-yl-methylphosphinodithioic acid)] analog of 3-H led to the formation and isolation of (phenyl)(6- methylpyridin-2-ylmethyl)phosphinodithioic acid, [2-C 5H 3N(6-CH 3)]CH 2P(S)(SH)(Ph) (6-H), that was characterized by spectroscopic methods and single crystal X-ray diffraction analysis. As found with 3-H, 6-H, adopts a zwitterionic structural form (6′).

KW - Cd(II)

KW - Complexation constants

KW - Dithiophosphinic acid

KW - Protonation constants

KW - Pt(II) complexes

KW - Pyridyl

KW - X-ray crystal structures

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JO - Polyhedron

JF - Polyhedron

SN - 0277-5387

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