Palladium(II) complexes of N,N-dimethylpyrrole-1- and 2-carbothioamides

Masakazu Fukazawa, Masakazu Kita, Matsuo Nonoyama

Research output: Contribution to journalArticle

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Abstract

The reaction of the sodium salt of pyrrole with N,N-dimethylthiocarbamoyl chloride in N,N-dimethylformamide gave N,N-dimethylpyrrole-1-carbothioamide (Hnpt), while the reaction of pyrrole with N,N-dimethylthiocarbamoyl chloride under phase transfer conditions afforded N,N-dimethylpyrrole-2-carbothioamide (Hapt), together with a very small amount of N,N,N′,N′-tetramethylpyrrole-1,2-dicarbothioamide. Hnpt and Hapt were metallated with lithium tetrachloropalladate in methanol to yield PdCl(npt) and PdCl(apt), respectively. Both complexes reacted with tri-n-butylphosphine (PBu3) and 4-tert-butyl-pyridine (tbp), forming PdCl(npt)(PBu3), PdCl(npt)(tbp), PdCl(apt)(PBu3) and PdCl(apt)(tbp). These and some additional complexes were characterized spectroscopically. In the npt complexes, the ligand was cyclopalladated at C(2) of the pyrrole ring, forming a five-membered, organometallic chelate ring accompanied by thioamide sulphur coordination. In the apt complexes, the ligand acted as a bidentate NS chelate, the ring NH proton being deprotonated. The X-ray analysis of PdCl(npt)(PBu3) and PdCl(apt)(PBu3) confirmed the coordination modes.

Original languageEnglish
Pages (from-to)1609-1617
Number of pages9
JournalPolyhedron
Volume13
Issue number10
DOIs
Publication statusPublished - 1994
Externally publishedYes

Fingerprint

Pyrroles
Palladium
pyrroles
Pyridine
palladium
pyridines
chelates
rings
Thioamides
chlorides
Ligands
Dimethylformamide
ligands
X ray analysis
Organometallics
Lithium
Sulfur
Methanol
Protons
sulfur

ASJC Scopus subject areas

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

Cite this

Palladium(II) complexes of N,N-dimethylpyrrole-1- and 2-carbothioamides. / Fukazawa, Masakazu; Kita, Masakazu; Nonoyama, Matsuo.

In: Polyhedron, Vol. 13, No. 10, 1994, p. 1609-1617.

Research output: Contribution to journalArticle

Fukazawa, Masakazu ; Kita, Masakazu ; Nonoyama, Matsuo. / Palladium(II) complexes of N,N-dimethylpyrrole-1- and 2-carbothioamides. In: Polyhedron. 1994 ; Vol. 13, No. 10. pp. 1609-1617.
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abstract = "The reaction of the sodium salt of pyrrole with N,N-dimethylthiocarbamoyl chloride in N,N-dimethylformamide gave N,N-dimethylpyrrole-1-carbothioamide (Hnpt), while the reaction of pyrrole with N,N-dimethylthiocarbamoyl chloride under phase transfer conditions afforded N,N-dimethylpyrrole-2-carbothioamide (Hapt), together with a very small amount of N,N,N′,N′-tetramethylpyrrole-1,2-dicarbothioamide. Hnpt and Hapt were metallated with lithium tetrachloropalladate in methanol to yield PdCl(npt) and PdCl(apt), respectively. Both complexes reacted with tri-n-butylphosphine (PBu3) and 4-tert-butyl-pyridine (tbp), forming PdCl(npt)(PBu3), PdCl(npt)(tbp), PdCl(apt)(PBu3) and PdCl(apt)(tbp). These and some additional complexes were characterized spectroscopically. In the npt complexes, the ligand was cyclopalladated at C(2) of the pyrrole ring, forming a five-membered, organometallic chelate ring accompanied by thioamide sulphur coordination. In the apt complexes, the ligand acted as a bidentate NS chelate, the ring NH proton being deprotonated. The X-ray analysis of PdCl(npt)(PBu3) and PdCl(apt)(PBu3) confirmed the coordination modes.",
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AB - The reaction of the sodium salt of pyrrole with N,N-dimethylthiocarbamoyl chloride in N,N-dimethylformamide gave N,N-dimethylpyrrole-1-carbothioamide (Hnpt), while the reaction of pyrrole with N,N-dimethylthiocarbamoyl chloride under phase transfer conditions afforded N,N-dimethylpyrrole-2-carbothioamide (Hapt), together with a very small amount of N,N,N′,N′-tetramethylpyrrole-1,2-dicarbothioamide. Hnpt and Hapt were metallated with lithium tetrachloropalladate in methanol to yield PdCl(npt) and PdCl(apt), respectively. Both complexes reacted with tri-n-butylphosphine (PBu3) and 4-tert-butyl-pyridine (tbp), forming PdCl(npt)(PBu3), PdCl(npt)(tbp), PdCl(apt)(PBu3) and PdCl(apt)(tbp). These and some additional complexes were characterized spectroscopically. In the npt complexes, the ligand was cyclopalladated at C(2) of the pyrrole ring, forming a five-membered, organometallic chelate ring accompanied by thioamide sulphur coordination. In the apt complexes, the ligand acted as a bidentate NS chelate, the ring NH proton being deprotonated. The X-ray analysis of PdCl(npt)(PBu3) and PdCl(apt)(PBu3) confirmed the coordination modes.

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