Skip to main content
SpringerLink
Log in

Inclusion Compounds of the Host 9-(4-Methylphenyl)-9H-xanthen-9-ol with a Series of Organic Guests

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

The host 9-(4-methylphenyl)-9H-xanthen-9-ol (H) forms inclusion compounds with the guests cyclohexane (H · ½CHEX), benzene (H · ½BENZ), 1,4-dioxane (H · ½DIOX), cyclohexanone (H · CYONE), N,N-dimethylformamide (H · DMF) and N,N-dimethylacetamide (H · DMA). For those guest molecules possessing electron acceptor atoms/functionalities hydrogen bonding with the host is the prominent mode of interaction and presents itself in the form of (Host)–OH···O(Guest) linkages. The cyclohexane and benzene guests however, occupy voids created by neighbouring host molecules which form hydrogen bonded dimers of the form (Host)–OH···O(Host). The structures of the inclusion compounds were investigated and their thermal stabilities determined. Selectivity experiments were also conducted.

Graphical Abstract

The host 9-(4-methylphenyl)-9H-xanthen-9-ol (H) forms inclusion compounds with the guests cyclohexane (H · ½CHEX), benzene (H · ½BENZ), 1,4-dioxane (H · ½DIOX), cyclohexanone (H · CYONE), N,N-dimethylformamide (H · DMF) and N,N-dimethylacetamide (H · DMA). Crystal structures and thermal stabilities were determined. The host selectivity was also investigated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Norman A, Rahman AA, Bishop R, Craig DC, Scudder ML (2003) Eur J Org Chem 1:72–81

    Google Scholar 

  2. Rao CNR, Vivekchand SRC, Biswas K, Govindaraj A (2007) Dalton Trans 3728–3749. doi:10.1039/b708342d

  3. Friedman N, Speiser S, Kaftory M (2006) Cryst Growth Des 6:1653. doi:10.1021/cg060107j

    Article  Google Scholar 

  4. Kumar VSS, Pigge FC, Rath NP (2006) Cryst Growth Des 6:193. doi:10.1021/cg050270z

    Article  CAS  Google Scholar 

  5. Scott JL, Almesaker A, Sumi Y, Tanaka K (2007) Cryst Growth Des 7:1049. doi:10.1021/cg060522b

    Article  CAS  Google Scholar 

  6. Alshahateet SF, Ong TT, Bishop R, Kooli F, Messali M (2006) Cryst Growth Des 6:1676. doi:10.1021/cg0601352

    Article  CAS  Google Scholar 

  7. Jacobs A, Nassimbeni LR, Su H, Taljaard B (2005) Org Biomol Chem 3:1319. doi:10.1039/b416331a

    Article  CAS  Google Scholar 

  8. Jacobs A, Faleni N, Nassimbeni LR, Taljaard JH (2007) Cryst Growth Des 7:1003. doi:10.1021/cg060792u

    Article  CAS  Google Scholar 

  9. Dilthey W, Quint F, Heinen J (1939) J Prakt Chem 152:49–98. doi:10.1002/prac.19391520301

    Article  CAS  Google Scholar 

  10. COLLECT data collection software (1998) Nonius, Delft, Netherlands

  11. Otwinowski Z, Minor W (1997) Methods in enzymology. In: Carter CW, Sweet RM (eds) Macromolecular crystallography, part A, vol 276. Academic Press, New York, pp 307–326

    Chapter  Google Scholar 

  12. Sheldrick GM (1990) Acta Crystallogr A 46:467. doi:10.1107/S0108767390000277

    Article  Google Scholar 

  13. Sheldrick GM (1997) SHELX-97, A program for crystal structure determination. University of Göttingen, Germany

    Google Scholar 

  14. Barbour LJ (2001) Supramol Chem (Kyoto) 1:189

    Article  CAS  Google Scholar 

  15. Olovsson I, Jönsson P (1975) In: Schuster P, Zundel G, Sardify C (eds) The hydrogen bond-structure and spectroscopy. North Holland Publishing Company, USA

  16. Farrugia LJ (1997) J Appl Cryst 30:565. doi:10.1107/S0021889897003117

    Article  CAS  Google Scholar 

  17. Spek AL (1990) Acta Crystallogr A 46:C34

    Google Scholar 

  18. Barbour LJ (1999) J Appl Cryst 32:353. doi:10.1107/S0021889898012679

    Article  CAS  Google Scholar 

  19. Brown ME (1988) Introduction to thermal analysis. Chapman & Hall, New York Chapter 13

    Google Scholar 

  20. Flynn JH, Wall LA (1966) Polym Lett 4:323. doi:10.1002/pol.1966.110040504

    Article  CAS  Google Scholar 

  21. Caira MR, Jacobs A, Nassimbeni LR (2004) Supramol Chem (Kyoto) 16:337

    Article  CAS  Google Scholar 

  22. Caira MR, Jacobs A, Nassimbeni LR, Toda F (2003) Cryst Eng Comm 5(28):150–153

    Google Scholar 

  23. Pivotar AM, Holman KT, Ward MD (2001) Chem Mater 13:3018. doi:10.1021/cm0104452

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Cape Peninsula University of Technology, PO Box 652, Cape Town, 8000, South Africa

    N. Faleni & A. Jacobs

  2. Sasol Technology, R&D, Klasie Havenga Road 1, Sasolburg, South Africa

    J. H. Taljaard

Authors
  1. N. Faleni
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Jacobs
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. J. H. Taljaard
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. Jacobs.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Faleni, N., Jacobs, A. & Taljaard, J.H. Inclusion Compounds of the Host 9-(4-Methylphenyl)-9H-xanthen-9-ol with a Series of Organic Guests. J Chem Crystallogr 39, 285–292 (2009). https://doi.org/10.1007/s10870-008-9475-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-008-9475-y

Keywords

Search

Navigation