Mononuclear zinc(II) and mercury(II) complexes of Schiff bases derived from pyrrolealdehyde and cysteamine containing intramolecular NH⋯S hydrogen bonds

Kuan Yi Wu, Chang Chih Hsieh, Yih-Chern Horng

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Abstract

Two neutral group 12 metal complexes, bis(pyrrol-2-ylmethyleneaminoethylthio)zinc(II) (1) and bis(pyrrol-2-ylmethyleneaminoethylthio)mercury(II) (2), with the (Nimine)2S2 coordination mode were synthesized by using metal-templated Schiff base condensation, and their molecular structures were determined by X-ray diffraction analysis. Complex 1 exhibits a distorted tetrahedral geometry around the metal, whereas the metal center has a bisphenoidal configuration in complex 2. Both mononuclear complexes possess intramolecular NH⋯S hydrogen bonds, as evidenced by IR, 1H NMR and X-ray crystallography. The hydrogen-bond donor (H-Npyrrole) and acceptor (S atom) are coming from different ligands within a single molecule. Complex 2 represents the first example of a mercury complex in the N2S2 coordination mode with intramolecular NH⋯S hydrogen-bond interactions. An investigation of the effects of the NH⋯S hydrogen bonding on the stability of 1 and 2, using an N-methyl pyrrolyl analogue, demonstrated that the N-H hydrogen-bond donor from the pyrrolyl moiety probably played a role in the stability of 1, but not 2.

Original languageEnglish
Pages (from-to)2085-2091
Number of pages7
JournalJournal of Organometallic Chemistry
Volume694
Issue number13
DOIs
Publication statusPublished - 2009 Jun 1

Fingerprint

cysteamine
Cysteamine
Schiff Bases
Mercury (metal)
Mercury
imines
Zinc
Hydrogen
Hydrogen bonds
zinc
hydrogen bonds
Metals
metals
X Ray Crystallography
Coordination Complexes
Hydrogen Bonding
Molecular Structure
X-Ray Diffraction
crystallography
X ray crystallography

All Science Journal Classification (ASJC) codes

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

Cite this

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title = "Mononuclear zinc(II) and mercury(II) complexes of Schiff bases derived from pyrrolealdehyde and cysteamine containing intramolecular NH⋯S hydrogen bonds",
abstract = "Two neutral group 12 metal complexes, bis(pyrrol-2-ylmethyleneaminoethylthio)zinc(II) (1) and bis(pyrrol-2-ylmethyleneaminoethylthio)mercury(II) (2), with the (Nimine)2S2 coordination mode were synthesized by using metal-templated Schiff base condensation, and their molecular structures were determined by X-ray diffraction analysis. Complex 1 exhibits a distorted tetrahedral geometry around the metal, whereas the metal center has a bisphenoidal configuration in complex 2. Both mononuclear complexes possess intramolecular NH⋯S hydrogen bonds, as evidenced by IR, 1H NMR and X-ray crystallography. The hydrogen-bond donor (H-Npyrrole) and acceptor (S atom) are coming from different ligands within a single molecule. Complex 2 represents the first example of a mercury complex in the N2S2 coordination mode with intramolecular NH⋯S hydrogen-bond interactions. An investigation of the effects of the NH⋯S hydrogen bonding on the stability of 1 and 2, using an N-methyl pyrrolyl analogue, demonstrated that the N-H hydrogen-bond donor from the pyrrolyl moiety probably played a role in the stability of 1, but not 2.",
author = "Wu, {Kuan Yi} and Hsieh, {Chang Chih} and Yih-Chern Horng",
year = "2009",
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T1 - Mononuclear zinc(II) and mercury(II) complexes of Schiff bases derived from pyrrolealdehyde and cysteamine containing intramolecular NH⋯S hydrogen bonds

AU - Wu, Kuan Yi

AU - Hsieh, Chang Chih

AU - Horng, Yih-Chern

PY - 2009/6/1

Y1 - 2009/6/1

N2 - Two neutral group 12 metal complexes, bis(pyrrol-2-ylmethyleneaminoethylthio)zinc(II) (1) and bis(pyrrol-2-ylmethyleneaminoethylthio)mercury(II) (2), with the (Nimine)2S2 coordination mode were synthesized by using metal-templated Schiff base condensation, and their molecular structures were determined by X-ray diffraction analysis. Complex 1 exhibits a distorted tetrahedral geometry around the metal, whereas the metal center has a bisphenoidal configuration in complex 2. Both mononuclear complexes possess intramolecular NH⋯S hydrogen bonds, as evidenced by IR, 1H NMR and X-ray crystallography. The hydrogen-bond donor (H-Npyrrole) and acceptor (S atom) are coming from different ligands within a single molecule. Complex 2 represents the first example of a mercury complex in the N2S2 coordination mode with intramolecular NH⋯S hydrogen-bond interactions. An investigation of the effects of the NH⋯S hydrogen bonding on the stability of 1 and 2, using an N-methyl pyrrolyl analogue, demonstrated that the N-H hydrogen-bond donor from the pyrrolyl moiety probably played a role in the stability of 1, but not 2.

AB - Two neutral group 12 metal complexes, bis(pyrrol-2-ylmethyleneaminoethylthio)zinc(II) (1) and bis(pyrrol-2-ylmethyleneaminoethylthio)mercury(II) (2), with the (Nimine)2S2 coordination mode were synthesized by using metal-templated Schiff base condensation, and their molecular structures were determined by X-ray diffraction analysis. Complex 1 exhibits a distorted tetrahedral geometry around the metal, whereas the metal center has a bisphenoidal configuration in complex 2. Both mononuclear complexes possess intramolecular NH⋯S hydrogen bonds, as evidenced by IR, 1H NMR and X-ray crystallography. The hydrogen-bond donor (H-Npyrrole) and acceptor (S atom) are coming from different ligands within a single molecule. Complex 2 represents the first example of a mercury complex in the N2S2 coordination mode with intramolecular NH⋯S hydrogen-bond interactions. An investigation of the effects of the NH⋯S hydrogen bonding on the stability of 1 and 2, using an N-methyl pyrrolyl analogue, demonstrated that the N-H hydrogen-bond donor from the pyrrolyl moiety probably played a role in the stability of 1, but not 2.

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