Synthesis, spectroscopic characterization and x-ray studies of new complexes of organotin(IV) chlorides with n-alkylated 2-amino-1-cyclopentene-1-carbodithioic acids

Abbas Tarassoli, Tahereh Sedaghat, Monte Helm, Arlan D. Norman

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The new complexes [Ph2SnCl(BuACDA)] (1), [Ph 3Sn(BuACDA)] (2), [Bu2Sn(BuACDA)2] (3), [Ph2SnCl-(EtACDA)] (4), [Ph3Sn(EtACDA)] (5) and [Bu 2Sn(EtACDA)2] (6) have been prepared from reactions between 2-N-butylamino-1-cyclopentene-1-carbodithioic acid (BuACDA) or 2-N-ethylamino-1-cyclopentene-1-carbodithioic acid (EtACDA) and Ph 2SnCl2, Ph3SnCl or Bu2SnCl 2. The 1H NMR, 119Sn NMR, UV-Vis and IR data and the elemental analyses support the structures of these organotin compounds. In all these complexes, the S-H proton has been removed and coordination takes place through the carbodithioate group. The 119Sn NMR data are consistent with the presence of five-coordinated tin(IV) in solution. Structures of 1 and 3 have also been confirmed by single crystal X-ray crystallography. The crystals of both are triclinic with space group P1. In the structure of 1, the tin environment is distorted trigonal bipyramidal with the Cl and one of the sulfur atoms in apical positions. In the structure of 3 the overall geometry at tin is highly distorted trans octahedral with the four S atoms on the equatorial plane. In both complexes, the ligand is asymmetrically chelated to the tin and there is an intramolecular hydrogen bond between the sulfur and the proton of the amine group.

Original languageEnglish
Pages (from-to)1179-1189
Number of pages11
JournalJournal of Coordination Chemistry
Volume56
Issue number13
DOIs
Publication statusPublished - Sep 10 2003

Fingerprint

Cyclopentanes
Chlorides
chlorides
Tin
X rays
acids
Acids
synthesis
tin
x rays
Nuclear magnetic resonance
Sulfur
nuclear magnetic resonance
Protons
sulfur
Organotin Compounds
Atoms
protons
X ray crystallography
crystallography

Keywords

  • Carbodithioate complexes
  • Organotin
  • X-ray crystallography

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Synthesis, spectroscopic characterization and x-ray studies of new complexes of organotin(IV) chlorides with n-alkylated 2-amino-1-cyclopentene-1-carbodithioic acids. / Tarassoli, Abbas; Sedaghat, Tahereh; Helm, Monte; Norman, Arlan D.

In: Journal of Coordination Chemistry, Vol. 56, No. 13, 10.09.2003, p. 1179-1189.

Research output: Contribution to journalArticle

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abstract = "The new complexes [Ph2SnCl(BuACDA)] (1), [Ph 3Sn(BuACDA)] (2), [Bu2Sn(BuACDA)2] (3), [Ph2SnCl-(EtACDA)] (4), [Ph3Sn(EtACDA)] (5) and [Bu 2Sn(EtACDA)2] (6) have been prepared from reactions between 2-N-butylamino-1-cyclopentene-1-carbodithioic acid (BuACDA) or 2-N-ethylamino-1-cyclopentene-1-carbodithioic acid (EtACDA) and Ph 2SnCl2, Ph3SnCl or Bu2SnCl 2. The 1H NMR, 119Sn NMR, UV-Vis and IR data and the elemental analyses support the structures of these organotin compounds. In all these complexes, the S-H proton has been removed and coordination takes place through the carbodithioate group. The 119Sn NMR data are consistent with the presence of five-coordinated tin(IV) in solution. Structures of 1 and 3 have also been confirmed by single crystal X-ray crystallography. The crystals of both are triclinic with space group P1. In the structure of 1, the tin environment is distorted trigonal bipyramidal with the Cl and one of the sulfur atoms in apical positions. In the structure of 3 the overall geometry at tin is highly distorted trans octahedral with the four S atoms on the equatorial plane. In both complexes, the ligand is asymmetrically chelated to the tin and there is an intramolecular hydrogen bond between the sulfur and the proton of the amine group.",
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N2 - The new complexes [Ph2SnCl(BuACDA)] (1), [Ph 3Sn(BuACDA)] (2), [Bu2Sn(BuACDA)2] (3), [Ph2SnCl-(EtACDA)] (4), [Ph3Sn(EtACDA)] (5) and [Bu 2Sn(EtACDA)2] (6) have been prepared from reactions between 2-N-butylamino-1-cyclopentene-1-carbodithioic acid (BuACDA) or 2-N-ethylamino-1-cyclopentene-1-carbodithioic acid (EtACDA) and Ph 2SnCl2, Ph3SnCl or Bu2SnCl 2. The 1H NMR, 119Sn NMR, UV-Vis and IR data and the elemental analyses support the structures of these organotin compounds. In all these complexes, the S-H proton has been removed and coordination takes place through the carbodithioate group. The 119Sn NMR data are consistent with the presence of five-coordinated tin(IV) in solution. Structures of 1 and 3 have also been confirmed by single crystal X-ray crystallography. The crystals of both are triclinic with space group P1. In the structure of 1, the tin environment is distorted trigonal bipyramidal with the Cl and one of the sulfur atoms in apical positions. In the structure of 3 the overall geometry at tin is highly distorted trans octahedral with the four S atoms on the equatorial plane. In both complexes, the ligand is asymmetrically chelated to the tin and there is an intramolecular hydrogen bond between the sulfur and the proton of the amine group.

AB - The new complexes [Ph2SnCl(BuACDA)] (1), [Ph 3Sn(BuACDA)] (2), [Bu2Sn(BuACDA)2] (3), [Ph2SnCl-(EtACDA)] (4), [Ph3Sn(EtACDA)] (5) and [Bu 2Sn(EtACDA)2] (6) have been prepared from reactions between 2-N-butylamino-1-cyclopentene-1-carbodithioic acid (BuACDA) or 2-N-ethylamino-1-cyclopentene-1-carbodithioic acid (EtACDA) and Ph 2SnCl2, Ph3SnCl or Bu2SnCl 2. The 1H NMR, 119Sn NMR, UV-Vis and IR data and the elemental analyses support the structures of these organotin compounds. In all these complexes, the S-H proton has been removed and coordination takes place through the carbodithioate group. The 119Sn NMR data are consistent with the presence of five-coordinated tin(IV) in solution. Structures of 1 and 3 have also been confirmed by single crystal X-ray crystallography. The crystals of both are triclinic with space group P1. In the structure of 1, the tin environment is distorted trigonal bipyramidal with the Cl and one of the sulfur atoms in apical positions. In the structure of 3 the overall geometry at tin is highly distorted trans octahedral with the four S atoms on the equatorial plane. In both complexes, the ligand is asymmetrically chelated to the tin and there is an intramolecular hydrogen bond between the sulfur and the proton of the amine group.

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