RESEARCH ARTICLE

 

Hydrogen bonding patterns in a series of 3-spirocyclic oxindoles

 

 

Andreas Lemmerer^*; Joseph P. Michael

Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, P.O. WITS 2050, South Africa

 

 

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ABSTRACT

The crystal structures of the new compounds spiro[cyclohexane-1,3'-indol]-2'(1'H)-one (1), (rel-1R,2S)-spiro[bicyclo[2.2.1] heptane-2,3'-indol]-2'(1'H)-one (2) and spiro[indole-3,2'-tricyclo[3.3.1.1^3,7]decan]-2(1H)-one (3) have been determined by low temperature single crystal X-ray diffraction. The effects of substitution on the hydrogen bonding pattern is compared between all three compounds.

Keywords: Hydrogen bonding, X-ray crystal structure, oxindoles, Cambridge Structural Database

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Acknowledgements

This material is based upon work supported financially by the National Research Foundation, Pretoria (GUN 2053652). Any opinions, findings and conclusions or recommendations expressed in this material are those of the authors and therefore the NRF does not accept any liability in regard thereto. This work was also supported by the University of the Witwaters-rand, which is thanked for providing the infrastructure required to do this work.

 

References and Notes

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26 Search Query: Molecular fragment oxindole backbone, any substituents on the 3-position. Filters: 3D coordinates determined, R factor < 0.075, not disordered, no errors, no ions, no powder structures, only organics. 167 hits which was reduced to 135 by manually removing duplicate entries, entries containing solvent molecules, and those containing no H atom coordinates.

 

 

Received 24 May 2010
Revised 5 October 2010
Accepted 29 October 2010

 

 

*To whom correspondence should be addressed. E-mail: andreas.lemmerer@wits.ac.za