Solid state study of sulfoxide adducts of (2-amidoethyl-C,O) trihalostannanes: Supramolecular networks constructed from hydrogen-bonds involving the amido units

R. Alan Howie, Geraldo M. De Lima, James L. Wardell*, Solange M.S.V. Wardell, William T.A. Harrison

*Corresponding author for this work

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The complex, (H 2NCOCH 2CH 2-C,O)(L)) SnCl 3, (L = EtCONH 2-O), isolated from a reaction mixture containing hydrochloric acid, tin and acrylamide in Et 2O solution, undergoes ligand exchange reactions with sulfoxides (sulfoxide = dimethyl sulfoxide, tetramethylene sulfoxide, 2-phenyl-1,3-dithiane trans-1-oxide and 2-phenyl-1,3-dithiane trans-1-trans-3-dioxide) to give (H 2NCOCH 2CH 2-C,O)(sulfoxide-O)SnCl 3. The tin centres in all the complexes are hexa-coordinated with a fac-CCl 3O 2 donor set, in which the octahedral geometries are somewhat distorted due to variations in the Sn-halide bond lengths, exemplifying the trans effect, and the small bite angles of the chelating (2-amidoethyl-C,O) ligand. The 2-phenyl-1,3-dithiane-1,3-dioxide ligand acts only as a monodentate ligand in its complex. The supramolecular structures are dominated by intermolecular hydrogen bonds with the NH 2 groups as the donor species. Halide exchange between (H 2NCOCH 2CH 2-C,O)- (tetramethylene sulfoxide-O)SnCl 3 and bromide ion was shown to give the mixed halide complex (H 2NCOCH 2CH 2-C,O) (tetramethylene sulfoxide-O)SnCl 1.5Br 1.5).

Original languageEnglish
Pages (from-to)62-69
Number of pages8
JournalJournal of Organometallic Chemistry
Volume716
Early online date18 Jun 2012
DOIs
Publication statusPublished - 1 Oct 2012

Fingerprint

sulfoxide
adducts
Hydrogen
Hydrogen bonds
Ligands
hydrogen bonds
halides
solid state
ligands
Tin
dioxides
tin
Sulfoxides
Dimethyl sulfoxide
Hydrochloric Acid
Acrylamide
hydrochloric acid
Bond length
Bites and Stings
Hydrochloric acid

Keywords

  • 2-Amidoethyl
  • Bidentate ligand
  • Hydrogen bond
  • Sulfoxide ligand
  • Tin(IV) complex
  • Trans- effect

ASJC Scopus subject areas

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

Cite this

Solid state study of sulfoxide adducts of (2-amidoethyl-C,O) trihalostannanes : Supramolecular networks constructed from hydrogen-bonds involving the amido units. / Howie, R. Alan; De Lima, Geraldo M.; Wardell, James L.; Wardell, Solange M.S.V.; Harrison, William T.A.

In: Journal of Organometallic Chemistry, Vol. 716, 01.10.2012, p. 62-69.

Research output: Contribution to journalArticle

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title = "Solid state study of sulfoxide adducts of (2-amidoethyl-C,O) trihalostannanes: Supramolecular networks constructed from hydrogen-bonds involving the amido units",
abstract = "The complex, (H 2NCOCH 2CH 2-C,O)(L)) SnCl 3, (L = EtCONH 2-O), isolated from a reaction mixture containing hydrochloric acid, tin and acrylamide in Et 2O solution, undergoes ligand exchange reactions with sulfoxides (sulfoxide = dimethyl sulfoxide, tetramethylene sulfoxide, 2-phenyl-1,3-dithiane trans-1-oxide and 2-phenyl-1,3-dithiane trans-1-trans-3-dioxide) to give (H 2NCOCH 2CH 2-C,O)(sulfoxide-O)SnCl 3. The tin centres in all the complexes are hexa-coordinated with a fac-CCl 3O 2 donor set, in which the octahedral geometries are somewhat distorted due to variations in the Sn-halide bond lengths, exemplifying the trans effect, and the small bite angles of the chelating (2-amidoethyl-C,O) ligand. The 2-phenyl-1,3-dithiane-1,3-dioxide ligand acts only as a monodentate ligand in its complex. The supramolecular structures are dominated by intermolecular hydrogen bonds with the NH 2 groups as the donor species. Halide exchange between (H 2NCOCH 2CH 2-C,O)- (tetramethylene sulfoxide-O)SnCl 3 and bromide ion was shown to give the mixed halide complex (H 2NCOCH 2CH 2-C,O) (tetramethylene sulfoxide-O)SnCl 1.5Br 1.5).",
keywords = "2-Amidoethyl, Bidentate ligand, Hydrogen bond, Sulfoxide ligand, Tin(IV) complex, Trans- effect",
author = "Howie, {R. Alan} and {De Lima}, {Geraldo M.} and Wardell, {James L.} and Wardell, {Solange M.S.V.} and Harrison, {William T.A.}",
note = "Acknowledgements The use of the EPSRC X-ray crystallographic service at Southampton and the valuable assistance of the staff there is gratefully acknowledged. We thank CAPES for financial support.",
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TY - JOUR

T1 - Solid state study of sulfoxide adducts of (2-amidoethyl-C,O) trihalostannanes

T2 - Supramolecular networks constructed from hydrogen-bonds involving the amido units

AU - Howie, R. Alan

AU - De Lima, Geraldo M.

AU - Wardell, James L.

AU - Wardell, Solange M.S.V.

AU - Harrison, William T.A.

N1 - Acknowledgements The use of the EPSRC X-ray crystallographic service at Southampton and the valuable assistance of the staff there is gratefully acknowledged. We thank CAPES for financial support.

PY - 2012/10/1

Y1 - 2012/10/1

N2 - The complex, (H 2NCOCH 2CH 2-C,O)(L)) SnCl 3, (L = EtCONH 2-O), isolated from a reaction mixture containing hydrochloric acid, tin and acrylamide in Et 2O solution, undergoes ligand exchange reactions with sulfoxides (sulfoxide = dimethyl sulfoxide, tetramethylene sulfoxide, 2-phenyl-1,3-dithiane trans-1-oxide and 2-phenyl-1,3-dithiane trans-1-trans-3-dioxide) to give (H 2NCOCH 2CH 2-C,O)(sulfoxide-O)SnCl 3. The tin centres in all the complexes are hexa-coordinated with a fac-CCl 3O 2 donor set, in which the octahedral geometries are somewhat distorted due to variations in the Sn-halide bond lengths, exemplifying the trans effect, and the small bite angles of the chelating (2-amidoethyl-C,O) ligand. The 2-phenyl-1,3-dithiane-1,3-dioxide ligand acts only as a monodentate ligand in its complex. The supramolecular structures are dominated by intermolecular hydrogen bonds with the NH 2 groups as the donor species. Halide exchange between (H 2NCOCH 2CH 2-C,O)- (tetramethylene sulfoxide-O)SnCl 3 and bromide ion was shown to give the mixed halide complex (H 2NCOCH 2CH 2-C,O) (tetramethylene sulfoxide-O)SnCl 1.5Br 1.5).

AB - The complex, (H 2NCOCH 2CH 2-C,O)(L)) SnCl 3, (L = EtCONH 2-O), isolated from a reaction mixture containing hydrochloric acid, tin and acrylamide in Et 2O solution, undergoes ligand exchange reactions with sulfoxides (sulfoxide = dimethyl sulfoxide, tetramethylene sulfoxide, 2-phenyl-1,3-dithiane trans-1-oxide and 2-phenyl-1,3-dithiane trans-1-trans-3-dioxide) to give (H 2NCOCH 2CH 2-C,O)(sulfoxide-O)SnCl 3. The tin centres in all the complexes are hexa-coordinated with a fac-CCl 3O 2 donor set, in which the octahedral geometries are somewhat distorted due to variations in the Sn-halide bond lengths, exemplifying the trans effect, and the small bite angles of the chelating (2-amidoethyl-C,O) ligand. The 2-phenyl-1,3-dithiane-1,3-dioxide ligand acts only as a monodentate ligand in its complex. The supramolecular structures are dominated by intermolecular hydrogen bonds with the NH 2 groups as the donor species. Halide exchange between (H 2NCOCH 2CH 2-C,O)- (tetramethylene sulfoxide-O)SnCl 3 and bromide ion was shown to give the mixed halide complex (H 2NCOCH 2CH 2-C,O) (tetramethylene sulfoxide-O)SnCl 1.5Br 1.5).

KW - 2-Amidoethyl

KW - Bidentate ligand

KW - Hydrogen bond

KW - Sulfoxide ligand

KW - Tin(IV) complex

KW - Trans- effect

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U2 - 10.1016/j.jorganchem.2012.05.050

DO - 10.1016/j.jorganchem.2012.05.050

M3 - Article

AN - SCOPUS:84865028956

VL - 716

SP - 62

EP - 69

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -