The University of Southampton
University of Southampton Institutional Repository

Chirality in cyclotriphosphazenes with one stereogenic centre

Chirality in cyclotriphosphazenes with one stereogenic centre
Chirality in cyclotriphosphazenes with one stereogenic centre
Mono-substitution reactions of gem symmetrically disubstituted cyclophosphazenes such as (1) and (2) provide a convenient way to investigate the chiral configurational properties of cyclophosphazene compounds with one stereogenic centre. Previous work by X-ray crystallography has shown that the mono-dibenzylamino derivative of (1), compound (3a), is chiral and exists as a racemate. In this work, compound (1) was reacted with piperidine, dimethylamine, pyrrolidine and phenol to give compounds (3b-3e), respectively, and compound (2) was reacted with dimethylamine to give (4). The structures and stereogenic properties of new compounds (3b), (3c) and (4) were determined by X-ray crystallography and, together with compound (3a), the chirality was confirmed by P-31 NMR spectroscopy on addition of a chiral solvating agent (CSA), (S)-(+)-2,2,2-trifluoro-l-(9' -anthryl)ethanol. As compound (3d) did not give crystals suitable for X-ray crystallography and compound (3e) is an oil, their stereogenic properties were confirmed by P-31 NMR spectroscopy on addition of CSA. The work confirms that cyclophosphazene derivatives containing one centre of chirality exist as racemates and shows that the chiral properties of such molecules may be determined by P-31 NMR spectroscopy on addition of a chiral solvating agent in those cases where X-ray crystal structures are not available.
cyclotriphosphazene derivatives, chirality, crystal structures, nmr, csa (chiral solvating agent), phosphorus-nitrogen compounds, x-ray, crystallography, nuclear-magnetic-resonance, cl33p3n3 compounds, crystal-structure, nongeminal-2, 4, 6-trichloro-2, 6-trisdimethylaminocyclotriphosphazatriene, hexachlorocyclotriphosphazatriene, cyclophosphazenes, configurations, phosphazenes
842-846
Besli, Serap
0127fb56-1156-4946-b5cb-789828fe9ffb
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
Kilic, Adem
1bf0a2d7-b8c6-4740-bd84-89b8db4c5769
Shaw, Robert A.
a9ecde60-6fe9-4b5d-86e3-77cd5dcfaab8
Uslu, Aylin
95af2437-3473-4022-8070-ad7d36524a87
Yesilot, Serkan
9e239a86-5bc2-4697-9bc5-ac30363af673
Besli, Serap
0127fb56-1156-4946-b5cb-789828fe9ffb
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
Kilic, Adem
1bf0a2d7-b8c6-4740-bd84-89b8db4c5769
Shaw, Robert A.
a9ecde60-6fe9-4b5d-86e3-77cd5dcfaab8
Uslu, Aylin
95af2437-3473-4022-8070-ad7d36524a87
Yesilot, Serkan
9e239a86-5bc2-4697-9bc5-ac30363af673

Besli, Serap, Coles, Simon J., Davies, David B., Eaton, Robert J., Hursthouse, Michael B., Kilic, Adem, Shaw, Robert A., Uslu, Aylin and Yesilot, Serkan (2004) Chirality in cyclotriphosphazenes with one stereogenic centre. Inorganic Chemistry Communications, 7 (7), 842-846. (doi:10.1016/j.inoche.2004.04.023).

Record type: Article

Abstract

Mono-substitution reactions of gem symmetrically disubstituted cyclophosphazenes such as (1) and (2) provide a convenient way to investigate the chiral configurational properties of cyclophosphazene compounds with one stereogenic centre. Previous work by X-ray crystallography has shown that the mono-dibenzylamino derivative of (1), compound (3a), is chiral and exists as a racemate. In this work, compound (1) was reacted with piperidine, dimethylamine, pyrrolidine and phenol to give compounds (3b-3e), respectively, and compound (2) was reacted with dimethylamine to give (4). The structures and stereogenic properties of new compounds (3b), (3c) and (4) were determined by X-ray crystallography and, together with compound (3a), the chirality was confirmed by P-31 NMR spectroscopy on addition of a chiral solvating agent (CSA), (S)-(+)-2,2,2-trifluoro-l-(9' -anthryl)ethanol. As compound (3d) did not give crystals suitable for X-ray crystallography and compound (3e) is an oil, their stereogenic properties were confirmed by P-31 NMR spectroscopy on addition of CSA. The work confirms that cyclophosphazene derivatives containing one centre of chirality exist as racemates and shows that the chiral properties of such molecules may be determined by P-31 NMR spectroscopy on addition of a chiral solvating agent in those cases where X-ray crystal structures are not available.

Full text not available from this repository.

More information

Published date: 1 July 2004
Keywords: cyclotriphosphazene derivatives, chirality, crystal structures, nmr, csa (chiral solvating agent), phosphorus-nitrogen compounds, x-ray, crystallography, nuclear-magnetic-resonance, cl33p3n3 compounds, crystal-structure, nongeminal-2, 4, 6-trichloro-2, 6-trisdimethylaminocyclotriphosphazatriene, hexachlorocyclotriphosphazatriene, cyclophosphazenes, configurations, phosphazenes

Identifiers

Local EPrints ID: 20134
URI: https://eprints.soton.ac.uk/id/eprint/20134
PURE UUID: eca1ac82-d090-45e8-bc3e-4a48c1696443
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 22 Feb 2006
Last modified: 20 Jul 2019 01:09

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of https://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×