Eu (hfc) 3

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Structural formula
Structural formula of Eu (hfc) 3
(+) - enantiomer of the compound
General
Surname Eu (hfc) 3
other names
  • Europium (III) -tris [(1 R ) -3- (heptafluorobutanoyl) camphorate]
  • Tris [3- (2,2,3,3,4,4,4-heptafluorobutyryl) bornane-2-onato- O , O '] europium
  • Eu (hfbc) 3
Molecular formula C 42 H 42 EuF 21 O 6
Brief description

dark yellow powder

External identifiers / databases
CAS number 34788-82-4
EC number 252-214-0
ECHA InfoCard 100,047,452
PubChem 10931233
Wikidata Q61675352
properties
Molar mass 1193.73 g mol −1
Physical state

firmly

Melting point

156-158 ° C

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Eu (hfc) 3 (formerly Eu (hfbc) 3 ) is an enantiomerically pure organic compound of europium , which appears as a dark yellow powder.

use

Eu (hfc) 3 is an optically active lanthanoid shift reagent . It is used to determine the enantiomeric purity of a chiral substance by means of NMR spectroscopy . The compound causes diastereomeric complexes to form, the peaks of which are positioned differently. By integrating related peaks, the diastereomeric ratio can be determined and, as a rule, conclusions can be drawn from this about the enantiomeric ratio .

The compound is used not only as a shift reagent, but also as a catalyst in enantioselective Diels-Alder reactions . A high enantioselectivity is achieved in particular through the use of chiral auxiliaries.

properties

The compound is readily soluble in organic solvents such as dichloromethane or chloroform . The specific angle of rotation is [α] D 20 + 158.0 ° Like many lanthanoid shift reagents (LSR), Eu (hfc) 3 is also a hygroscopic compound.

Eu (hfc) 3 is structurally related to Eu (tfc) 3 and has a perfluorinated alkyl chain two carbon atoms longer on the camphor backbone. In studies, (+) - Eu (hfc) 3 showed a stronger enantiomeric splitting in NMR spectra compared to (+) - Eu (tfc) 3 .

safety instructions

Strong oxidizing agents can cause strong reactions with Eu (hfc) 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 Datasheet Europium tris [3- (heptafluoropropylhydroxymethylene) - (+) - camphorate] from Sigma-Aldrich , accessed on February 10, 2019 ( PDF ).
  2. ↑ Entry on Eu (hfc) 3 . In: Römpp Online . Georg Thieme Verlag, accessed on February 10, 2019.
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ↑ a b Lanthanide Shift Reagents. (No longer available online.) In: paperplane.io. Archived from the original on February 12, 2019 ; accessed on February 10, 2019 .
  5. ↑ Barry M. Trost (Ed.): Additions to C-X bonds . Elsevier , 1992, ISBN 978-0-08-091245-5 , Optical induction in the Eu (hfc) 3 -catalyzed reaction, pp. 682–685 ( limited preview in Google Book Search).
  6. ↑ 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 .