Eu (tfc) 3

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Structural formula
Structural formula of Eu (hfc) 3
Structural formula of the (+) - enantiomer of Eu (tfc) 3
General
Surname Eu (tfc) 3
other names
  • Europium (3+) tris [(1 Z ) -2,2,2-trifluoro-1- (4,7,7-trimethyl-3-oxobicyclo [2.2.1] hept-2-ylidene) ethanolate] ( IUPAC )
  • Eu (facam) 3
  • EuTFC
  • Europium (III) tris [3- (trifluoromethylhydroxymethylene) -d-camphorate]
  • Tris (3-trifluoroacetyl-d-camphorato) europium (III)
  • Tris [3- (trifluoromethylhydroxymethylene) -d-camphorate] europium (III)
Molecular formula C 36 H 42 EuF 9 O 6
Brief description

yellow-orange powder

External identifiers / databases
CAS number 34830-11-0
EC number 252-232-9
ECHA InfoCard 100,047,469
PubChem 5490153
ChemSpider 4590285
Wikidata Q84863062
properties
Molar mass 893.66 g mol −1
Physical state

firmly

Melting point

195-200 ° C

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Eu (tfc) 3 (formerly Eu (facam) 3 ) is an enantiomerically pure organic compound of europium , which appears as a yellow-orange powder.

use

Eu (tfc) 3 is mainly used in NMR spectroscopy . Since it is enantiomerically pure itself , it can form diastereomeric aggregates with other substances. Thus , enantiomeric ratios can be clarified in NMR, indirectly via the diastereomeric ratio . It can also be used to determine the absolute configuration of alcohols .

Structure and properties

Both enantiomers of Eu (tfc) 3 exist , which are derived from (+) - or (-) - camphor. However, many studies only examine the (+) - enantiomer. There are many reasons for using (+) - camphor. The enantiomerically pure compound is characterized by high availability, crystallinity and a large number of possible transformations that allow chiral ligands to be produced.

Eu (tfc) 3 is structurally closely related to Eu (hfc) 3 and only differs in the length of the perfluorinated residue on the camphor skeleton. The shorter chain in the tfc ligand leads to a poorer splitting of the signals in NMR spectra. It is soluble in chloroform but insoluble in water. Like most lanthanoid shift reagents, the compound is hygroscopic.

safety instructions

Strong oxidizing agents can cause strong reactions with Eu (tfc) 3 . Hydrogen fluoride , carbon monoxide and carbon dioxide and europium oxides are the decomposition products of the compound.

Individual evidence

  1. ↑ a b c d e data sheet Tris (trifluoromethylhydroxymethylene-d-camphorato) europium (III) from AlfaAesar, accessed on February 11, 2020 ( PDF )(JavaScript required) .
  2. ↑ a b Indranath Ghosh, Hongbo Zeng, Yoshito Kishi: Application of Chiral Lanthanide Shift Reagents for Assignment of Absolute Configuration of Alcohols . In: Organic Letters . tape 6 , no. December 25 , 2004, p. 4715-4718 , doi : 10.1021 / ol048061f .
  3. ↑ a b Mariane Axt, João Alifantes, Valentim Emílio Uberti Costa: Use of chiral lanthanide shift reagents in the elucidation of NMR signals from enantiomeric mixtures of polycyclic compounds . In: Journal of the Chemical Society Perkin Transactions 2 . tape 0 , no. 12 , 1999, p. 2783-2788 , doi : 10.1039 / A904473F .
  4. ^ W. Oppolzer: Camphor as a natural source of chirality in asymmetric synthesis . In: Pure and Applied Chemistry . tape 62 , no. 7 , January 1, 1990, ISSN  1365-3075 , pp. 1241–1250 , doi : 10.1351 / pac199062071241 ( degruyter.com [accessed February 13, 2020]).
  5. ↑ Europium tris (3- (trifluoromethylhydroxymethylene) - (+) - camphorate) | CAS 34830-11-0. Retrieved February 11, 2020 .