http://www.cnr.it/ontology/cnr/individuo/prodotto/ID48255
Chirality in the Absence of Rigid Stereogenic Elements: The Absolute Configuration of Residual Enantiomers of C3-Symmetric Propellers (Articolo in rivista)
- Type
- Label
- Chirality in the Absence of Rigid Stereogenic Elements: The Absolute Configuration of Residual Enantiomers of C3-Symmetric Propellers (Articolo in rivista) (literal)
- Anno
- 2009-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1002/chem.200801489 (literal)
- Alternative label
Benincori, T.; Marchesi, A.; Mussini, P.R.; Pilati, T.; Ponti, A.; Rizzo, S.; Sannicolo, F. (2009)
Chirality in the Absence of Rigid Stereogenic Elements: The Absolute Configuration of Residual Enantiomers of C3-Symmetric Propellers
in Chemistry - A European Journal
(literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Benincori, T.; Marchesi, A.; Mussini, P.R.; Pilati, T.; Ponti, A.; Rizzo, S.; Sannicolo, F. (literal)
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- Rivista
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#note
- DOI: 10.1002/chem.200801489 (literal)
- Note
- ISI Web of Science (WOS) (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
- [a] Prof. T. Benincori
Dipartimento di Scienze Chimiche ed Ambientali
Università dell'Insubria, via Valleggio 11
22100 Como (Italy)
[b] Dr. A. Marchesi
Laboratori Alchemia s.r.l., via S. Faustino 68
20134 Milano (Italy)
[c] Prof. P. R. Mussini
Dipartimento di Chimica Fisica ed Elettrochimica
Universit? di Milano, via Venezian 21
20133 Milano (Italy)
[d] Dr. T. Pilati, Dr. A. Ponti, Dr. S. Rizzo, Prof. F. Sannicol?
Istituto di Scienze e Tecnologie Molecolari (ISTM) CNR
via Golgi 19, 20133 Milano (Italy)
E-mail: francesco.sannicolo@unimi.it
[e] Prof. F. Sannicol?
Dipartimento di Chimica Organica e Industriale
C.I.MA.I.NA., Universit? di Milano, ISTM, CNR
via Venezian 21, 20133 Milano (Italy)
Fax: (+39) 02-5031-4139
Supporting information for (literal)
- Titolo
- Chirality in the Absence of Rigid Stereogenic Elements: The Absolute Configuration of Residual Enantiomers of C3-Symmetric Propellers (literal)
- Abstract
- Two new tris(aryl)phosphane oxides existing as configurationally stable residual enantiomers have been synthesised and their racemates resolved by semipreparative HPLC on a chiral stationary phase (CSP HPLC). One of them, recognised as a conglomerate, could be resolved by fractional crystallisation at a preparative scale level. In this case, the absolute configuration of the propeller-shaped molecule was determined by anomalous X-ray scattering. The problem of the correlative assignment of the absolute configuration to all known C-3-symmetric three-bladed propeller-shaped molecules existing as stable residual enantiomers is discussed. The configurational stability of the new chiral phosphane oxides and of the corresponding phosphanes was
evaluated by CD signal decay kinetics and dynamic H-1 NMR spectroscopy.
The racemisation barriers in phosphanes were found about 10 kcal
mol(-1) lower than those found for the corresponding oxides, though
geometry and inter-ring gearing would be very similar in the two
series. Configurational stability of residual tris(aryl)phosphanes was
found to be influenced by the electronic availability of the phosphorus
centre, as evaluated by electrochemical CV experiments. (literal)
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