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Synthesis and solid-state characterisation of 4-substituted methylidene oxindoles

Synthesis and solid-state characterisation of 4-substituted methylidene oxindoles
Synthesis and solid-state characterisation of 4-substituted methylidene oxindoles
Background: 4-substituted methylidene oxindoles are pharmacologically important. Detailed analysis and comparison of all the interactions present in crystal structures is necessary to understand how these structures arise. The XPac procedure allows comparison of complete crystal structures of related families of compounds to identify assemblies that are mainly the result of close-packing as well as networks of directed interactions.

Results: Five 4-substituted methylidene oxindoles have been synthesized by the Knoevenagel condensation of oxindole with para-substituted aromatic aldehydes and were characterized in the solid state by x-ray crystallography. Hence, the structures of (3E)-3-(4-Bromobenzylidene)-1,3-dihydro-2H-indol-2-one, 3a, (3E)-3-(4-Chlorobenzylidene)-1,3-dihydro-2H-indol-2-one, 3b, (3E)-3-(4-Methoxybenzylidene)-1,3-dihydro-2H-indol-2-one, 3c, (3E)-3-(4-Methylbenzylidene)-1,3-dihydro-2H-indol-2-one, 3d and (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one, 3e, were elucidated using single crystal X-ray crystallography.

Conclusions: A hydrogen bonded dimer molecular assembly or supramolecular construct was identified in all the crystal structures examined along with a further four 1D supramolecular constructs which were common to at least two of the family of structures studied. The 1D supramolecular constructs indicate that once the obvious strong interaction is satisfied to form hydrogen bonded dimer it is the conventionally weaker interactions, such as steric bulk and edge-to-face interactions which compete to influence the final structure formation.
1-10
Tizzard, Graham J.
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Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Edwards, Mark
0b95b131-86cc-4ee7-b5fd-4694d9acbf0d
Onyeabo, Romanus Oforbike
a61ebc1d-9da6-407f-824e-77fb6c62e8d7
Allen, Mark
f200a4d3-e0b7-4f7d-a095-749afd52c415
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Edwards, Mark
0b95b131-86cc-4ee7-b5fd-4694d9acbf0d
Onyeabo, Romanus Oforbike
a61ebc1d-9da6-407f-824e-77fb6c62e8d7
Allen, Mark
f200a4d3-e0b7-4f7d-a095-749afd52c415
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4

Tizzard, Graham J., Coles, Simon J., Edwards, Mark, Onyeabo, Romanus Oforbike, Allen, Mark and Spencer, John (2013) Synthesis and solid-state characterisation of 4-substituted methylidene oxindoles. Chemistry Central Journal, 7, 1-10. (doi:10.1186/1752-153X-7-182).

Record type: Article

Abstract

Background: 4-substituted methylidene oxindoles are pharmacologically important. Detailed analysis and comparison of all the interactions present in crystal structures is necessary to understand how these structures arise. The XPac procedure allows comparison of complete crystal structures of related families of compounds to identify assemblies that are mainly the result of close-packing as well as networks of directed interactions.

Results: Five 4-substituted methylidene oxindoles have been synthesized by the Knoevenagel condensation of oxindole with para-substituted aromatic aldehydes and were characterized in the solid state by x-ray crystallography. Hence, the structures of (3E)-3-(4-Bromobenzylidene)-1,3-dihydro-2H-indol-2-one, 3a, (3E)-3-(4-Chlorobenzylidene)-1,3-dihydro-2H-indol-2-one, 3b, (3E)-3-(4-Methoxybenzylidene)-1,3-dihydro-2H-indol-2-one, 3c, (3E)-3-(4-Methylbenzylidene)-1,3-dihydro-2H-indol-2-one, 3d and (3E)-3-(4-Nitrobenzylidene)-1,3-dihydro-2H-indol-2-one, 3e, were elucidated using single crystal X-ray crystallography.

Conclusions: A hydrogen bonded dimer molecular assembly or supramolecular construct was identified in all the crystal structures examined along with a further four 1D supramolecular constructs which were common to at least two of the family of structures studied. The 1D supramolecular constructs indicate that once the obvious strong interaction is satisfied to form hydrogen bonded dimer it is the conventionally weaker interactions, such as steric bulk and edge-to-face interactions which compete to influence the final structure formation.

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More information

Published date: 20 December 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry

Identifiers

Local EPrints ID: 362497
URI: http://eprints.soton.ac.uk/id/eprint/362497
PURE UUID: 7511f84c-da99-4f8c-87f7-ea29c9d18b6e
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 25 Feb 2014 16:13
Last modified: 18 Feb 2021 16:57

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Contributors

Author: Simon J. Coles ORCID iD
Author: Mark Edwards
Author: Romanus Oforbike Onyeabo
Author: Mark Allen
Author: John Spencer

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