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

Tizzard, Graham J, Coles, Simon J, Edwards, Mark, Oforbike Onyeabo, Romanus, Allen, Mark and Spencer, John (2013) Synthesis and solid-state characterisation of 4-substituted methylidene oxindoles. Chemistry Central Journal, 7. pp. 182-191. ISSN 1752-153X

[img] PDF - Published Version
Available under License Creative Commons Attribution.

Download (2MB)

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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science
Related URLs:
Depositing User: Deeptima Massey
Date Deposited: 30 Sep 2014 10:29
Last Modified: 15 Mar 2017 04:29
URI: http://sro.sussex.ac.uk/id/eprint/50417

View download statistics for this item

📧 Request an update