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

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

doi:10.1016/j.ica.2004.09.036

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

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

Chemistry

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

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 (Et₄N)[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 language	English (US)
Pages (from-to)	633-640
Number of pages	8
Journal	Inorganica Chimica Acta
Volume	358
Issue number	3
DOIs	https://doi.org/10.1016/j.ica.2004.09.036
State	Published - Feb 10 2005

Keywords

Carbamoyl methyl xanthate
Crystal structure
Hydrogen bond
Nickel tris ethylxanthate

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.ica.2004.09.036

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

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 (Et4N)[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 {\AA}.",

keywords = "Carbamoyl methyl xanthate, Crystal structure, Hydrogen bond, Nickel tris ethylxanthate",

author = "Walters, {Marc A.} and Justin Barad and Anthony Sireci and Golen, {James A.} and Rheingold, {Arnold L.}",

year = "2005",

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T2 - The free xanthate anion and ligand sulfur in nickel tris ethylxanthate

AU - Walters, Marc A.

AU - Barad, Justin

AU - Sireci, Anthony

AU - Golen, James A.

AU - Rheingold, Arnold L.

PY - 2005/2/10

Y1 - 2005/2/10

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 (Et4N)[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 (Et4N)[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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Xanthate sulfur as a hydrogen bond acceptor: The free xanthate anion and ligand sulfur in nickel tris ethylxanthate

Abstract

Keywords

ASJC Scopus subject areas

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