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1,3-diindolylureas and 1,3-diindolythioureas: anion complexation studies in solution and the solid State

1,3-diindolylureas and 1,3-diindolythioureas: anion complexation studies in solution and the solid State
1,3-diindolylureas and 1,3-diindolythioureas: anion complexation studies in solution and the solid State
1,3-Diindolylureas and thioureas have been synthesised and their anion complexation properties in solution studied. Whilst diindolylthioureas showed only moderate afinities and selectivities, diindolyureas show remarkably high affinity for dihydrogen phosphate in solution for an acyclic, neural receptor in water/[D-6]DMSO mixtures. These easy-to-make compounds adopt relatively planar conformations in the solid-state and are able to donate four hydrogen bonds and yet not fill the coordination sphere of carbonate or phosphate, allowing two or three receptors to bind to each anion in the solid-state.
anions, indoles, phosphate, structure elucidation, ureas
0947-6539
10236-10243
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0
Hiscock, Jennifer R.
2e1470fc-e298-492e-b50a-f1b590d224db
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark Edward
cf57314e-6856-491b-a8d2-2dffc452e161
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0
Hiscock, Jennifer R.
2e1470fc-e298-492e-b50a-f1b590d224db
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, Mark Edward
cf57314e-6856-491b-a8d2-2dffc452e161
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943

Caltagirone, Claudia, Hiscock, Jennifer R., Hursthouse, Michael B., Light, Mark Edward and Gale, Philip A. (2008) 1,3-diindolylureas and 1,3-diindolythioureas: anion complexation studies in solution and the solid State. Chemistry - A European Journal, 14 (33), 10236-10243. (doi:10.1002/chem.200801639).

Record type: Article

Abstract

1,3-Diindolylureas and thioureas have been synthesised and their anion complexation properties in solution studied. Whilst diindolylthioureas showed only moderate afinities and selectivities, diindolyureas show remarkably high affinity for dihydrogen phosphate in solution for an acyclic, neural receptor in water/[D-6]DMSO mixtures. These easy-to-make compounds adopt relatively planar conformations in the solid-state and are able to donate four hydrogen bonds and yet not fill the coordination sphere of carbonate or phosphate, allowing two or three receptors to bind to each anion in the solid-state.

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More information

e-pub ahead of print date: 15 October 2008
Published date: 17 November 2008
Keywords: anions, indoles, phosphate, structure elucidation, ureas

Identifiers

Local EPrints ID: 67667
URI: https://eprints.soton.ac.uk/id/eprint/67667
ISSN: 0947-6539
PURE UUID: 43bc8794-deca-491b-bd1a-54a77100dd9f
ORCID for Mark Edward Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

Catalogue record

Date deposited: 02 Sep 2009
Last modified: 06 Jun 2018 12:54

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