Xanthate sulfur as a hydrogen bond acceptor: The free xanthate anion and ligand sulfur in nickel tris ethylxanthate

Marc Walters, Justin Barad, Anthony Sireci, James A. Golen, Arnold L. Rheingold

Research output: Contribution to journalArticle

Abstract

Xanthates, like thiolates, form a variety of complexes with metals in which coordinating sulfur can serve as a hydrogen bond acceptor. Nickel tris xanthate complexes [Ni(xan) 3] -, (xan = o-ethylxanthate, N-(carbamoylmethyl)ethylxanthate) have been synthesized and compared by a combination of X-ray crystallographic and spectroscopic measurements. Recent results from our studies of N-H⋯S hydrogen bonding interactions in metal-xanthate complexes shows N-S distances to be longer than those in related thiolate complexes, indicative of weaker hydrogen bonds for the xanthates. The complex (Et 4N)[N-(carbamoylmethyl)ethylxanthate)] adopts an extended conformation in both the solid state and solution and lacks either intraligand or intermolecular N-H⋯S hydrogen bonds. The complex (CTA)[Ni(exa) 3] exhibits N-H⋯S hydrogen bonds between the amide group of the counterion and the ligand sulfur. The amide-sulfur N-H⋯S distance is 3.567 Å.

Original languageEnglish (US)
Pages (from-to)633-640
Number of pages8
JournalInorganica Chimica Acta
Volume358
Issue number3
DOIs
StatePublished - Feb 10 2005

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Nickel
Sulfur
Anions
Hydrogen
Hydrogen bonds
Negative ions
sulfur
Ligands
nickel
hydrogen bonds
anions
ligands
Coordination Complexes
Amides
amides
Hydrogen Bonding
metals
Metal complexes
solid solutions
X-Rays

Keywords

  • Carbamoyl methyl xanthate
  • Crystal structure
  • Hydrogen bond
  • Nickel tris ethylxanthate

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Xanthate sulfur as a hydrogen bond acceptor : The free xanthate anion and ligand sulfur in nickel tris ethylxanthate. / Walters, Marc; Barad, Justin; Sireci, Anthony; Golen, James A.; Rheingold, Arnold L.

In: Inorganica Chimica Acta, Vol. 358, No. 3, 10.02.2005, p. 633-640.

Research output: Contribution to journalArticle

Walters, Marc ; Barad, Justin ; Sireci, Anthony ; Golen, James A. ; Rheingold, Arnold L. / Xanthate sulfur as a hydrogen bond acceptor : The free xanthate anion and ligand sulfur in nickel tris ethylxanthate. In: Inorganica Chimica Acta. 2005 ; Vol. 358, No. 3. pp. 633-640.
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T2 - The free xanthate anion and ligand sulfur in nickel tris ethylxanthate

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AU - Barad, Justin

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AU - Golen, James A.

AU - Rheingold, Arnold L.

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N2 - Xanthates, like thiolates, form a variety of complexes with metals in which coordinating sulfur can serve as a hydrogen bond acceptor. Nickel tris xanthate complexes [Ni(xan) 3] -, (xan = o-ethylxanthate, N-(carbamoylmethyl)ethylxanthate) have been synthesized and compared by a combination of X-ray crystallographic and spectroscopic measurements. Recent results from our studies of N-H⋯S hydrogen bonding interactions in metal-xanthate complexes shows N-S distances to be longer than those in related thiolate complexes, indicative of weaker hydrogen bonds for the xanthates. The complex (Et 4N)[N-(carbamoylmethyl)ethylxanthate)] adopts an extended conformation in both the solid state and solution and lacks either intraligand or intermolecular N-H⋯S hydrogen bonds. The complex (CTA)[Ni(exa) 3] exhibits N-H⋯S hydrogen bonds between the amide group of the counterion and the ligand sulfur. The amide-sulfur N-H⋯S distance is 3.567 Å.

AB - Xanthates, like thiolates, form a variety of complexes with metals in which coordinating sulfur can serve as a hydrogen bond acceptor. Nickel tris xanthate complexes [Ni(xan) 3] -, (xan = o-ethylxanthate, N-(carbamoylmethyl)ethylxanthate) have been synthesized and compared by a combination of X-ray crystallographic and spectroscopic measurements. Recent results from our studies of N-H⋯S hydrogen bonding interactions in metal-xanthate complexes shows N-S distances to be longer than those in related thiolate complexes, indicative of weaker hydrogen bonds for the xanthates. The complex (Et 4N)[N-(carbamoylmethyl)ethylxanthate)] adopts an extended conformation in both the solid state and solution and lacks either intraligand or intermolecular N-H⋯S hydrogen bonds. The complex (CTA)[Ni(exa) 3] exhibits N-H⋯S hydrogen bonds between the amide group of the counterion and the ligand sulfur. The amide-sulfur N-H⋯S distance is 3.567 Å.

KW - Carbamoyl methyl xanthate

KW - Crystal structure

KW - Hydrogen bond

KW - Nickel tris ethylxanthate

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