Crystallographic studies on a series of salts of 2,3,7-trihydroxy-9-phenyl-fluorone
Crystallographic studies on a series of salts of 2,3,7-trihydroxy-9-phenyl-fluorone
2,3,7-Trihydroxy-9-phenyl-fluorone (hereafter H3Z) has been synthesised in its H4Z+, H3Z, H2Z- and Z3- protonation states. X-ray crystal structure determinations have been carried out for (H4Z)(HSO4), H3Z, [EtiPr2NH]H2Z, solvated (PPh4)H2Z and solvated K3Z. In each of these salts the 9-phenyl group adopts a different orientation so as to be involved in intermolecular aromatic interactions. The 3- and 6-phenolic carbon-oxygen bond lengths show that double bond character can be delocalised from the ketone to the deprotonated phenoxide across the conjugated π system of the fluorone.
Amphoteric organic systems, Fluorones, X-ray crystallography
466-471
Abrahams, Brendan F.
9d8972b1-63c7-4ee8-b5b6-5ccfbcf3f798
McCormick, Laura J.
f1c2f8cd-adcc-4bbf-9289-0b33a006d2bb
Robson, Richard
2c74c03e-58f1-4fc3-9b11-ff00e28d09c8
28 February 2009
Abrahams, Brendan F.
9d8972b1-63c7-4ee8-b5b6-5ccfbcf3f798
McCormick, Laura J.
f1c2f8cd-adcc-4bbf-9289-0b33a006d2bb
Robson, Richard
2c74c03e-58f1-4fc3-9b11-ff00e28d09c8
Abrahams, Brendan F., McCormick, Laura J. and Robson, Richard
(2009)
Crystallographic studies on a series of salts of 2,3,7-trihydroxy-9-phenyl-fluorone.
Journal of Molecular Structure, 920 (1-3), .
(doi:10.1016/j.molstruc.2008.12.020).
Abstract
2,3,7-Trihydroxy-9-phenyl-fluorone (hereafter H3Z) has been synthesised in its H4Z+, H3Z, H2Z- and Z3- protonation states. X-ray crystal structure determinations have been carried out for (H4Z)(HSO4), H3Z, [EtiPr2NH]H2Z, solvated (PPh4)H2Z and solvated K3Z. In each of these salts the 9-phenyl group adopts a different orientation so as to be involved in intermolecular aromatic interactions. The 3- and 6-phenolic carbon-oxygen bond lengths show that double bond character can be delocalised from the ketone to the deprotonated phenoxide across the conjugated π system of the fluorone.
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Accepted/In Press date: 3 December 2008
Published date: 28 February 2009
Keywords:
Amphoteric organic systems, Fluorones, X-ray crystallography
Identifiers
Local EPrints ID: 437880
URI: http://eprints.soton.ac.uk/id/eprint/437880
ISSN: 0022-2860
PURE UUID: e3e5166f-fac3-403f-9761-de500aa5333f
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Date deposited: 21 Feb 2020 17:31
Last modified: 18 Mar 2024 03:56
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Author:
Brendan F. Abrahams
Author:
Richard Robson
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