Complexation with diol host compounds. Part 32.† Separation of lutidine isomers by 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol

Abstract

The title host compound forms inclusion compounds with 2,4-, 3,5- and 2,6-lutidine. In each case the host∶guest ratio is 1∶2 and the structures are stabilised by (Host)O–H  · · ·  N(Guest) hydrogen bonds. Competition experiments show that the host selects the guests in order of preference of 3,5-lutidine > 2,6-lutidine > 2,4-lutidine. These results are in general agreement with the lattice energy calculations.

References

1. F. Toda and K. Akagi, Tetrahedron Lett., 1968, 33, 3695.
2. E. Weber, in Inclusion Compounds, vol. 4, eds. J. L. Atwood, J. E. D. Davies and D. D. MacNicol, Oxford University Press, 1991, ch. 5, pp. 188–263.
3. F. Toda, K. Tanaka and A. Sekikawa, J. Chem. Soc., Chem. Commun., 1987, 279.
4. D. R. Bond, L. Johnson, L. R. Nassimbeni and F. Toda, J. Solid State Chem., 1991, 92, 179.
5. L. Johnson, L. R. Nassimbeni and F. Toda, Acta Crystallogr., Sect. B, 1992, 47, 827.
6. COLLECT, data collection software, Nonius, 1998.
7. Z. Otwinowski and W. Minor, “Processing of X-ray Diraction Data Collected in Oscillation Mode”, in Methods in Enzymology, Macromolecular Crystallography, part A, eds. C. W. Carter, Jr. and R. M. Sweet, Academic Press, 1997, vol. 276, pp. 307–326.
8. G. M. Sheldrick, SHELX-86, in Crystallographic Computing 3, eds. G. M. Sheldrick, C. Kruger and R. Goddard, Oxford University Press, Oxford, 1985, p. 175.
9. G. M. Sheldrick, SHELX-93: A Program for Crystal Structure Determination; University of Göttingen, Germany.
10. International Tables for Crystallography, Vol. A, ed. T. Hahn, D. Reidel Publishing Company, Dordrecht: Holland/Boston, USA, 1983, p. 105.
11. International Tables for Crystallography, Vol. A, ed. T. Hahn, D. Reidel Publishing Company, Dordrecht: Holland/Boston, USA, 1983, p. 181.
12. L. J. Barbour, X-Seed: a graphical interface for the SHELX programme, University of Missouri-Columbia, USA, 1999.
13. L. J. Barbour, SECTION, a computer program for the graphic display of cross sections through a unit cell, J. Appl. Chem., 1999, 32, 353.
14. W. D. S. Motherwell, EENY, Potential Energy Program, Cambridge University.
15. A. Gavezzotti, Crystallogr. Rev., 1998, 7, 5.
16. A. Vedani and J. D. Dunitz, J. Am. Chem. Soc., 1985, 107, 7653.
17. M. R. Caira, L. R. Nassimbeni, D. Vujovic, E. Weber and A. Wierig, Structural Chem., 1999, 10, 205.
18. M. R. Caira, L. R. Nassimbeni, D. Vujovic and F. Toda, J. Phys. Org. Chem., 1999, 12, 1.