Publication detail

Synthesis, reactivity and complexation studies of N,S exo-heterodisubstituted o-carborane ligands. Carborane as a platform to produce the uncommon bidentate chelating (pyridine)N-C-C-C-S(H) motif

TEIXIDOR, F. LAROMAINE, A. KIVEKAS, R. SILLANPAA, R. VINAS, C. VESPALEC, R. HORÁKOVÁ, H.

Original Title

Synthesis, reactivity and complexation studies of N,S exo-heterodisubstituted o-carborane ligands. Carborane as a platform to produce the uncommon bidentate chelating (pyridine)N-C-C-C-S(H) motif

Type

journal article - other

Language

English

Original Abstract

The synthesis of N,S-heterodisubstituted 1-(2'-pyridyl)-2-SR-1,2-closo-C2B10H10 compounds (R = Et, 2; R = Pr-i, 3) has been accomplished starting from 1-(2 '-pyridyl)-1,2-closo-C2B10H11 (1), and their partial deboronation reaction leading to the structurally chiral [7-(2 '-pyridyl)-8-SR-7,8-nido-C2B9H10](-) derivatives ( R = Et, [ 4]-; R = iPr, [ 5]-) has been studied. Capillary electrophoresis combined with the chiral selector alpha-cyclodextrin has permitted the separation of the electrophoretically pure racemic [7-(2 '-pyridyl)-8-SR-7,8-nido-C2B9H11](-) ions into two peaks each one corresponding to the interaction of one enantiomer with the alpha-cyclodextrin. The N,S-heterodisubstituted o-carborane containing a mercapto group, 1-(2 '-pyridyl)-2-SH-1,2-closo-C2B10H10, 1, is one of the two examples of a rigid bidentate chelating (pyridine) N-C-C-C-S(H) motif having been structurally fully characterized. To study the potential of such a binding site, 1 has been tested as a ligand with metal ions requiring different coordination numbers, two (Au+) and four (Pd2+ and Rh+). The crystal structures of the Pd(II) and Au(I) complexes are reported. For the Pd(II) complex, 1 acts as a bidentate ligand whereas for Au(I), 1 acts as a monodentate ligand through the thiolate.

Keywords

neutron-capture therapy; molecular-structure; capillary-electrophoresis; coordination properties; crystal-structures; derivatives; chemistry; ruthenium(ii); spectroscopy; degradation

Authors

TEIXIDOR, F.; LAROMAINE, A.; KIVEKAS, R.; SILLANPAA, R.; VINAS, C.; VESPALEC, R.; HORÁKOVÁ, H.

RIV year

2008

Released

5. 3. 2008

Publisher

The Royal Society of Chemistry

Location

London

ISBN

1477-9226

Periodical

DALTON TRANSACTIONS

Year of study

2008

Number

3

State

United Kingdom of Great Britain and Northern Ireland

Pages from

345

Pages to

354

Pages count

10

BibTex

@article{BUT49576,
  author="Radim {Vespalec} and Hana {Horáková}",
  title="Synthesis, reactivity and complexation studies of N,S exo-heterodisubstituted o-carborane ligands. Carborane as a platform to produce the uncommon bidentate chelating (pyridine)N-C-C-C-S(H) motif",
  journal="DALTON TRANSACTIONS",
  year="2008",
  volume="2008",
  number="3",
  pages="345--354",
  issn="1477-9226"
}