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Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives

Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives
Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives
The gem-disubstituted cyclotriphosphazene 1 reacted with piperazine (pip) to give the piperazine-bridged derivative 2, which is expected to exist in meso and racemic forms because the two PCl (pip) groups are stereogenic. The proton-decoupled 31P NMR spectrum of 2 gave rise to two similar sets of ABX signals in a 1:1 ratio, consistent with formation of diastereoisomers. The meso and racemic forms of compound 2 were separated by column chromatography on silica gel and characterised by elemental analysis, mass spectrometry, 31P NMR spectroscopy, and X-ray crystallography. Using HPLC with a chiral stationary phase, the racemic form of compound 2 was further separated into enantiomers, which were characterised by circular dichroism (CD) spectroscopy. This is the first report of the separation of enantiomers in the field of cyclophosphazene chemistry and hence the first CD spectra of derivatives in which the cyclophosphazene ring is at the chiral centre.
cyclotriphosphazene enantiomers, chiral hplc, circular dichroism, crystal structures, p-31 nmr, chiral solvating agent, hplc
0899-0042
438-443
Bui, Tam T.T.
7503d482-256f-413b-b5cf-48732e7c54f3
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Drake, Alex F.
5c9ebbef-9ae4-433c-ab61-d14bd55c2886
Eaton, Robert J.
e274676b-0499-47e1-8dbb-8d1ed908cdea
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Kiliç, Adem
53892b58-c3f9-4894-bdf9-6be70ab7611e
Shaw, Robert A.
a9ecde60-6fe9-4b5d-86e3-77cd5dcfaab8
Yeşilot, Serkan
6d82d5b6-173c-4ca4-bf2e-02676c18c8d0
Bui, Tam T.T.
7503d482-256f-413b-b5cf-48732e7c54f3
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Drake, Alex F.
5c9ebbef-9ae4-433c-ab61-d14bd55c2886
Eaton, Robert J.
e274676b-0499-47e1-8dbb-8d1ed908cdea
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Kiliç, Adem
53892b58-c3f9-4894-bdf9-6be70ab7611e
Shaw, Robert A.
a9ecde60-6fe9-4b5d-86e3-77cd5dcfaab8
Yeşilot, Serkan
6d82d5b6-173c-4ca4-bf2e-02676c18c8d0

Bui, Tam T.T., Coles, Simon J., Davies, David B., Drake, Alex F., Eaton, Robert J., Hursthouse, Michael B., Kiliç, Adem, Shaw, Robert A. and Yeşilot, Serkan (2005) Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives. Chirality, 17 (8), 438-443. (doi:10.1002/chir.20187).

Record type: Article

Abstract

The gem-disubstituted cyclotriphosphazene 1 reacted with piperazine (pip) to give the piperazine-bridged derivative 2, which is expected to exist in meso and racemic forms because the two PCl (pip) groups are stereogenic. The proton-decoupled 31P NMR spectrum of 2 gave rise to two similar sets of ABX signals in a 1:1 ratio, consistent with formation of diastereoisomers. The meso and racemic forms of compound 2 were separated by column chromatography on silica gel and characterised by elemental analysis, mass spectrometry, 31P NMR spectroscopy, and X-ray crystallography. Using HPLC with a chiral stationary phase, the racemic form of compound 2 was further separated into enantiomers, which were characterised by circular dichroism (CD) spectroscopy. This is the first report of the separation of enantiomers in the field of cyclophosphazene chemistry and hence the first CD spectra of derivatives in which the cyclophosphazene ring is at the chiral centre.

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Published date: 2005
Keywords: cyclotriphosphazene enantiomers, chiral hplc, circular dichroism, crystal structures, p-31 nmr, chiral solvating agent, hplc

Identifiers

Local EPrints ID: 20748
URI: https://eprints.soton.ac.uk/id/eprint/20748
ISSN: 0899-0042
PURE UUID: 6b45b485-9a8d-4fd7-b467-819221d55eba

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Date deposited: 02 Mar 2006
Last modified: 17 Jul 2017 16:28

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Contributors

Author: Tam T.T. Bui
Author: Simon J. Coles
Author: David B. Davies
Author: Alex F. Drake
Author: Robert J. Eaton
Author: Michael B. Hursthouse
Author: Adem Kiliç
Author: Robert A. Shaw
Author: Serkan Yeşilot

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