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Stereogenic properties of 1,3-disubstituted derivatives of cyclotriphosphazene: cis (meso) and trans (racemic) isomers

Stereogenic properties of 1,3-disubstituted derivatives of cyclotriphosphazene: cis (meso) and trans (racemic) isomers
Stereogenic properties of 1,3-disubstituted derivatives of cyclotriphosphazene: cis (meso) and trans (racemic) isomers
The di-spiro derivatives of the reaction of cyclotriphosphazene with either 3-amino-1-propanol or N-methylethanolamine are expected to exist as cis and trans geometric isomers and be meso and racemic, respectively. The isomers were separated by column chromatography on silica gel and analysed by elemental analysis, mass spectrometry, and P-31 and H-1 NMR spectroscopies. X-ray crystallography was used to characterise both the cis and trans isomers of the N-methylethanolamino di-spiro derivatives and the cis isomer of the propanolamino di-spiro derivative but, due to a mirror plane for the trans isomer, it was not possible to determine uniquely the NH and O positions and, hence, the cis or trans configuration of the compound. The stereogenic properties of all the compounds were investigated by P-31 NMR spectroscopy on addition of a chiral solvating agent (CSA), (S)-(+)-2,2,2-trifluoro-1-(9'-anthryl)ethanol. The CSA results confirm that both cis isomers are meso and the trans isomer of the N-methylethanolamino di-spiro derivative is a racemate, as expected. It was also shown that the second isomer of the propanolamino di-spiro derivative was a racemate, confirming that it is the trans isomer and, hence, confirming the original predictions of the stereogenicity of the 1,3-disubstituted cyclotriphosphazenes.
stereogenicity, crystal structures, cis-1, 3-cyclotriphosphazenes, trans-1, nmr, csa (chiral solvating agent)
657-661
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Eaton, Robert J.
e274676b-0499-47e1-8dbb-8d1ed908cdea
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Adem Kılıç, Adem
9d156723-f051-43aa-8a8b-542d204fd18a
Shaw, Robert A.
a9ecde60-6fe9-4b5d-86e3-77cd5dcfaab8
Şahin, Şule
3bc2452e-39b3-46b9-9035-1bbc2e9a6695
Uslu, Aylin
95af2437-3473-4022-8070-ad7d36524a87
Yeşilot, Serjkan
e0242eb6-f28d-42e9-8802-9e1d728fe603
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Eaton, Robert J.
e274676b-0499-47e1-8dbb-8d1ed908cdea
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Adem Kılıç, Adem
9d156723-f051-43aa-8a8b-542d204fd18a
Shaw, Robert A.
a9ecde60-6fe9-4b5d-86e3-77cd5dcfaab8
Şahin, Şule
3bc2452e-39b3-46b9-9035-1bbc2e9a6695
Uslu, Aylin
95af2437-3473-4022-8070-ad7d36524a87
Yeşilot, Serjkan
e0242eb6-f28d-42e9-8802-9e1d728fe603

Coles, Simon J., Davies, David B., Eaton, Robert J., Hursthouse, Michael B., Adem Kılıç, Adem, Shaw, Robert A., Şahin, Şule, Uslu, Aylin and Yeşilot, Serjkan (2004) Stereogenic properties of 1,3-disubstituted derivatives of cyclotriphosphazene: cis (meso) and trans (racemic) isomers. Inorganic Chemistry Communications, 7 (5), 657-661. (doi:10.1016/j.inoche.2004.01.012).

Record type: Article

Abstract

The di-spiro derivatives of the reaction of cyclotriphosphazene with either 3-amino-1-propanol or N-methylethanolamine are expected to exist as cis and trans geometric isomers and be meso and racemic, respectively. The isomers were separated by column chromatography on silica gel and analysed by elemental analysis, mass spectrometry, and P-31 and H-1 NMR spectroscopies. X-ray crystallography was used to characterise both the cis and trans isomers of the N-methylethanolamino di-spiro derivatives and the cis isomer of the propanolamino di-spiro derivative but, due to a mirror plane for the trans isomer, it was not possible to determine uniquely the NH and O positions and, hence, the cis or trans configuration of the compound. The stereogenic properties of all the compounds were investigated by P-31 NMR spectroscopy on addition of a chiral solvating agent (CSA), (S)-(+)-2,2,2-trifluoro-1-(9'-anthryl)ethanol. The CSA results confirm that both cis isomers are meso and the trans isomer of the N-methylethanolamino di-spiro derivative is a racemate, as expected. It was also shown that the second isomer of the propanolamino di-spiro derivative was a racemate, confirming that it is the trans isomer and, hence, confirming the original predictions of the stereogenicity of the 1,3-disubstituted cyclotriphosphazenes.

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Published date: 1 May 2004
Keywords: stereogenicity, crystal structures, cis-1, 3-cyclotriphosphazenes, trans-1, nmr, csa (chiral solvating agent)

Identifiers

Local EPrints ID: 20169
URI: https://eprints.soton.ac.uk/id/eprint/20169
PURE UUID: c5ce995e-7ef1-4b9d-ae95-3598d3c70270
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 22 Feb 2006
Last modified: 06 Jun 2018 12:54

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Contributors

Author: Simon J. Coles ORCID iD
Author: David B. Davies
Author: Robert J. Eaton
Author: Adem Adem Kılıç
Author: Robert A. Shaw
Author: Şule Şahin
Author: Aylin Uslu
Author: Serjkan Yeşilot

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