Solvent-assisted spontaneous resolution of a 16-membered ring containing gold(I) showing short Au⋯Au aurophilic interaction and a figure-eight conformation

Tünde Tunyogi, Andrea Deák, G. Tárkányi, P. Király, G. Pálinkás

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Abstract

The achiral 4,6-bis(diphenylphosphino) phenoxazine (nixantphos) ligand was used to synthesize a gold(I) complex, [Au2(nixantphos) 2](NO3)2, containing a 16-membered [Au 2(nixantphos)2]+2 cationic ring in a chiral figure-eight conformation. The single crystal X-ray diffraction analysis of [Au2(nixantphos)2](NO3)2· 3MeOH·H2O (1) and [Au2(nixantphos) 2](NO3)2·4MeCN (2) revealed a solvent-assisted spontaneous resolution of the [Au2(nixantphos) 2](NO3)2 complex. By changing the nature of the solvent, homochiral hydrogen bonded helices (1) and heterochiral hydrogen bonded monomers (2) were obtained. Multinuclear NMR spectroscopy showed the evidence of chemical exchange phenomenon related to the interconversion of the enantiomeric skeletons of the 16-membered macrocycle in solution. The existence of the Au⋯Au aurophilic interaction was confirmed by the analysis of the spin-system in the 31P NMR spectrum.

Original languageEnglish
Pages (from-to)2049-2055
Number of pages7
JournalInorganic Chemistry
Volume47
Issue number6
DOIs
Publication statusPublished - Mar 17 2008

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Gold
Conformations
Hydrogen
gold
nuclear magnetic resonance
rings
hydrogen
musculoskeletal system
helices
X ray diffraction analysis
Nuclear magnetic resonance spectroscopy
monomers
Monomers
Nuclear magnetic resonance
Single crystals
interactions
Ligands
ligands
single crystals
diffraction

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

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title = "Solvent-assisted spontaneous resolution of a 16-membered ring containing gold(I) showing short Au⋯Au aurophilic interaction and a figure-eight conformation",
abstract = "The achiral 4,6-bis(diphenylphosphino) phenoxazine (nixantphos) ligand was used to synthesize a gold(I) complex, [Au2(nixantphos) 2](NO3)2, containing a 16-membered [Au 2(nixantphos)2]+2 cationic ring in a chiral figure-eight conformation. The single crystal X-ray diffraction analysis of [Au2(nixantphos)2](NO3)2· 3MeOH·H2O (1) and [Au2(nixantphos) 2](NO3)2·4MeCN (2) revealed a solvent-assisted spontaneous resolution of the [Au2(nixantphos) 2](NO3)2 complex. By changing the nature of the solvent, homochiral hydrogen bonded helices (1) and heterochiral hydrogen bonded monomers (2) were obtained. Multinuclear NMR spectroscopy showed the evidence of chemical exchange phenomenon related to the interconversion of the enantiomeric skeletons of the 16-membered macrocycle in solution. The existence of the Au⋯Au aurophilic interaction was confirmed by the analysis of the spin-system in the 31P NMR spectrum.",
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T1 - Solvent-assisted spontaneous resolution of a 16-membered ring containing gold(I) showing short Au⋯Au aurophilic interaction and a figure-eight conformation

AU - Tunyogi, Tünde

AU - Deák, Andrea

AU - Tárkányi, G.

AU - Király, P.

AU - Pálinkás, G.

PY - 2008/3/17

Y1 - 2008/3/17

N2 - The achiral 4,6-bis(diphenylphosphino) phenoxazine (nixantphos) ligand was used to synthesize a gold(I) complex, [Au2(nixantphos) 2](NO3)2, containing a 16-membered [Au 2(nixantphos)2]+2 cationic ring in a chiral figure-eight conformation. The single crystal X-ray diffraction analysis of [Au2(nixantphos)2](NO3)2· 3MeOH·H2O (1) and [Au2(nixantphos) 2](NO3)2·4MeCN (2) revealed a solvent-assisted spontaneous resolution of the [Au2(nixantphos) 2](NO3)2 complex. By changing the nature of the solvent, homochiral hydrogen bonded helices (1) and heterochiral hydrogen bonded monomers (2) were obtained. Multinuclear NMR spectroscopy showed the evidence of chemical exchange phenomenon related to the interconversion of the enantiomeric skeletons of the 16-membered macrocycle in solution. The existence of the Au⋯Au aurophilic interaction was confirmed by the analysis of the spin-system in the 31P NMR spectrum.

AB - The achiral 4,6-bis(diphenylphosphino) phenoxazine (nixantphos) ligand was used to synthesize a gold(I) complex, [Au2(nixantphos) 2](NO3)2, containing a 16-membered [Au 2(nixantphos)2]+2 cationic ring in a chiral figure-eight conformation. The single crystal X-ray diffraction analysis of [Au2(nixantphos)2](NO3)2· 3MeOH·H2O (1) and [Au2(nixantphos) 2](NO3)2·4MeCN (2) revealed a solvent-assisted spontaneous resolution of the [Au2(nixantphos) 2](NO3)2 complex. By changing the nature of the solvent, homochiral hydrogen bonded helices (1) and heterochiral hydrogen bonded monomers (2) were obtained. Multinuclear NMR spectroscopy showed the evidence of chemical exchange phenomenon related to the interconversion of the enantiomeric skeletons of the 16-membered macrocycle in solution. The existence of the Au⋯Au aurophilic interaction was confirmed by the analysis of the spin-system in the 31P NMR spectrum.

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