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South African Journal of Chemistry
versión On-line ISSN 1996-840X
versión impresa ISSN 0379-4350
S.Afr.j.chem. (Online) vol.63 Durban 2010
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
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[3.3.1.13,7]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
Full text available only in PDF format.
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
1 H. Takayama and S.I. Sakai, Gelsemium alkaloids, in The Alkaloids. Chemistry and Pharmacology, (G.A. Cordell, ed.), vol. 49, Academic Press, San Diego, USA, 1997, Chapter 1, pp. 1-78. [ Links ]
2 J.E. Saxton, Alkaloids of Mitragyna and related genera, in The Alkaloids. Chemistry and Physiology, (R.H.F. Manske, ed.), vol. 14. Academic Press, New York, USA, 1973, Chapter 3, pp. 123-156. [ Links ]
3 H. Takayama, M. Kitajima and N. Kogure, Curr. Org. Chem., 2005, 9, 1445-1464. [ Links ]
4 J.S. Bindra, Oxindole alkaloids, in The Alkaloids. Chemistry and Physiology, (R.H.F Manske, ed.), vol. 14, Academic Press, New York, USA, 1973, Chapter 2, pp. 83-121. [ Links ]
5 J. Polonsky, M.A. Merrien, T. Prangé and C. Pascard, J. Chem. Soc, Chem. Commun, 1980, 601-602. [ Links ]
6 M. Yamazaki, E. Okuyama, M. Kobayashi and H. Inoue, Tetrahedron Lett., 1981, 22, 135-136. [ Links ]
7 T.O. Larsen, K. Frydenvang, J.C. Frisvad and C. Christophersen, J. Nat. Prod., 1998, 61, 1154-1157. [ Links ]
8 T.O. Larsen, B.O. Petersen, J.O. Duus, D.Sorensen, J.C. Frisvad and M.E Hansen, J. Nat. Prod., 2005, 68, 871-874. [ Links ]
9 H. Lin and S.J. Danishefsky, Angew. Chem. Int. Ed., 2003, 42, 36-51. [ Links ]
10 R.M. Williams and R.J. Cox, Acc. Chem. Res., 2003, 36, 127-139. [ Links ]
11 C. Marti and E.M. Carreira, Eur. J. Org. Chem., 2003, 12, 2209-2219. [ Links ]
12 I. Fleming, M.A. Loreto, J.P. Michael and I.H.M. Wallace, Tetrahedron Lett., 1982, 23, 2053-2056. [ Links ]
13 I. Fleming, M.A. Loreto, I.H.M. Wallace and J.P. Michael, J. Chem. Soc., Perkin Trans. 1, 1986, 349-359. [ Links ]
14 C. Clarke, I. Fleming, J.M.D. Fortunak, P.T. Gallagher, M.C. Honan, A. Mann, C.O. Nübling, P. R. Raithby and J. J. Wolff, Tetrahedron, 1988, 44, 3931-3944. [ Links ]
15 A. Lemmerer and J.P. Michael, CrystEngComm, 2008, 10, 95-102. [ Links ]
16 J. Bernstein, R.E. Davis, L. Shimoni and N.L. Chang, Angew. Chem., Int. Ed. Engl., 1995, 34, 1555-1573. [ Links ]
17 F.H. Allen, Acta Cryst, 2002, B58, 380-388. Cambridge Structural Database, Vers. 5.31 (November 2008 update). Search Query: Molecular fragment -C(=O)-NH2, Filters: 3D coordinates determined, R factor < 0.075, not disordered, no errors, no ions, no powder structures, only organics. [ Links ]
18 Search Query: Molecular fragment -C(=O)-N(H)-C-, Filters: 3D coordinates determined, R factor < 0.075, not disordered, no errors, no ions, no powder structures, only organics.
19 Bruker, SMART and SAINT+, Ver. 6.02 (including XPREP), 1999, Bruker AXS Inc., Madison, WI, USA. [ Links ]
20 G.M. Sheldrick, Acta Cryst., 2003, A64, 112-122. [ Links ]
21 L.J. Farrugia, J. Appl. Cryst., 1999, 32, 837-838. [ Links ]
22 L.J. Farrugia, J. Appl. Cryst., 1997, 30, 565. [ Links ]
23 A.L. Spek, J. Appl. Cryst., 36, 7-13. [ Links ]
24 K. Brandenburg, Diamond, Ver. 2.1e, Crystal Impact GbR, Bonn, Germany. [ Links ]
25 F.H. Allen, O. Kennard, D.G. Watson, L. Brenner, A.G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1-S19. [ Links ]
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