Abstract
New chiral host compounds based on mandelic acid derivatives having methyl (6a, b and 8a, b) or bromo substituents (7a, b) attached to the phenyl ring of mandelic acid and involving additional aromatic groups were synthesized. The inclusion properties of both the racemic and the optically resolved host species are reported, including solvent co-crystallization as well as chiroselective and vapour sorptive inclusion. The structures of the free racemic host compound 6b and of the DMSO inclusion compounds of optically resolved and racemic 8 (8a and 8b, respectively) have been determined by X-ray analysis. Enantiomeric pairs of molecules in 6b form centro-symmetric dimers by mutual hydrogen bonding of one hydroxyl group while the other is involved in O-–H ... π interactions. The guest molecules in the DMSO complexes of 8a and 8b are bound via hydrogen bonds to two host molecules related by translation along crystallographic axes. Parallels to previous hosts of this type are drawn.
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G.R. Desiraju: Crystal Engineering (Materials ScienceMonographs, Vol. 54), Elsevier, Amsterdam (1989). (b) G.R. Desiraju (Ed.): The Crystal as a Supramolecular Entity (Perspectives in Supramolecular Chemistry, Vol. 2), Wiley, Chichester (1996). (c) G.R. Desiraju: Angew. Chem. 107, 2541 (1995); Angew. Chem. Int. Ed. Engl. 34, 2311 (1995).
R. Bishop, D.D. MacNicol, and F. Toda (Eds.): Comprehensive Supramolecular Chemistry, Vol. 6, Elsevier, Oxford (1996). (b) E. Weber (Ed.): Molecular Inclusion and Molecular Recognition – Clathrates I and II (Topics in Current Chemistry, Vols. 140 and 149), Springer-Verlag, Berlin-Heidelberg (1987 and 1988).
J.A. Swift, V.A. Russel, and M.D. Ward: Adv. Mater. 9, 1183 (1997). (b) C.L. Bowes and G.A. Ozin: Adv. Mater. 8, 13 (1996). (c) G.B. Gardner, D. Venkataraman, J.S. Moore, and S. Lee: Nature 374, 792 (1995).
J.L. Atwood, J.E.D. Davies, and D.D. MacNicol (Eds.): Inclusion Compounds, Vols. 1–3, Academic Press, London (1984); Vols. 4–5, Oxford University Press, Oxford (1991). (b) E. Weber: in J.I. Kroschwitz (Ed.), Kirk-Othmer Encyclopedia of Chemical Technology, 4th Ed., Vol. 14, Wiley, New York (1995), p. 122.
A. Ehlen, C. Wimmer, E. Weber, and J. Bargon: Angew. Chem. 105, 116 (1993); Angew. Chem. Int. Ed. Engl. 32, 110 (1993). (b) D. Meinhold, W. Seichter, K. KÖhnke, J. Seidel, and E. Weber: Adv. Mater. 9, 958 (1997).
F. Toda: Acc. Chem. Res. 28, 480 (1995). (b) F. Toda: Supramol. Chem. 6, 159 (1995). (c) D. Worsch and F. VÖgtle: in ref. 2(b), Vol. 140, p. 21.
F. Toda, K. Tanaka, M. Watanabe, T. Abe, and N. Harada: Tetrahedron: Asymmetry 6, 1495 (1995). (b) F. Toda and K. Tanaka: Tetrahedron Lett. 29, 551 (1988).
E. Weber and C. Wimmer: Chirality 5, 331 (1993). (b) E. Weber, C. Wimmer, A.L. Llamas-Saiz, and C. Foces-Foces: J. Chem. Soc., Chem. Commun. 733 (1992).
E. Weber, O. Hager, C. Foces-Foces, and A.L. Llamas-Saiz: J. Phys. Org. Chem. 9, 50 (1996).
E. Weber, O. Hager, C. Foces-Foces, and A.L. Llamas-Saiz: Supramol. Chem. 9, 85 (1998).
O. Hager, C. Foces-Foces, A. L. Llamas-Saiz, and E. Weber: Acta Crystallogr., Sect. B 54, 82 (1998).
B.B. Corson, R.A. Dodge, S.A. Harris, and J.J. Yeaw: Organic Synthesis Coll. Vol. I, 336 (1941).
J.L. Riebsomer, J. Irvine, and R. Andrews: J. Am. Chem. Soc. 60, 1015 (1938).
A. Skita, F. Keil, and H. Meiner: Ber. Dtsch. Chem. Ges. 66, 974 (1933).
J.J. Klingenberg: Organic Synthesis, Coll. Vol. IV, 110 (1963).
A.W. Ingersoll, S.H. Babcock, and F.B. Burns: J. Am. Chem. Soc. 55, 411 (1993).
R. Devant, U. Mahler, and M. Braun: Chem. Ber. 121, 397 (1988).
K. Nützel: in E. Müller (Ed.), Methoden der Organischen Chemie, (Houben-Weyl), Thieme, Stuttgart (1973), Vol. XIII/2a, p. 47.
J. Cosier and A.M. Glazer: J. Appl. Crystallogr. 19, 105 (1986).
A. Altomare, M.C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, and G. Polidori: J. Appl. Crystallogr. 435 (1994).
S.R. Hall, H.D. Flack, and J.M. Steward: Xtal3.2, Ed. Univ. of Western Australia, Perth, 1994.
N. Walker and D. Stuart: Acta Crystallogr., Sect. A 39, 158 (1983).
M. Martinez-Ripoll and F.H. Cano: unpublished work (1975).
A. Nardelli: Comput. Chem. 7, 95 (1983).
D. Flack: Acta Crystallogr., Sect. A 39, 876 (1983).
International Tables for X-Ray Crystallography, Vol. IV, Kynoch Press, Birmingham (1974).
H. R. Allcock: in ref. 4(a), Vol. 1, pp. 351.
A. Coetzee, L.R. Nassimbeni, and K. Achleitner: Thermochim. Acta 298, 81 (1997).
E. Weber, K. Skobridis, A. Wierig, S. Stathi, L.R. Nassimbeni, and M.L. Niven: Angew. Chem. 105, 616 (1993); Angew. Chem. Int. Ed. Engl. 32, 606 (1993).
T.H. Brehmer, P.P. Korkas, and E. Weber: Sensors and Actuators B 44, 595 (1997). (b) J. Lerchner, J. Seidel, G. Wolf, and E. Weber: Sensors and Actuators B 32, 71 (1996). (c) J. Reinbold, K. Buhlmann, K. Cammann, A. Wierig, C. Wimmer, and E. Weber: Sensors and Actuators B 18–19, 77 (1994).
A. Domenicano and P. Murray-Rust: Tetrahedron Lett. 24, 2283 (1979).
J.L. Atwood, F. Hamada, K.D. Robinson, G.W. Orr, and R.L. Vincent: Nature 349, 683 (1991). (b) S.S. Al-Juaid, A.K.A. Al-Nasr, C. Eaborn, and P. B. Hitchcock: J. Chem. Soc., Chem. Commun. 1482 (1991).
E. Weber, T. Hens, O. Gallardo, and I. CsÖregh: J. Chem. Soc., Perkin Trans. 2, 737 (1996).
E.B. Brouwer, G.D. Enright, and J.A. Ripmeester: Supramol. Chem. 7, 143 (1996). (b) G. Ferguson, J.F. Gallagher, Y. Li, M.A. McKervey, E. Madigan, J.F. Malone, M.B. Moran, and A. Walker: Supramol. Chem. 7, 223 (1996). (c) N. Yoshida, H. Oshio, and T. Ito: J. Chem. Soc., Chem. Commun. 63 (1998).
A. L. Llamas-Saiz, C. Foces-Foces, E. Weber, and C. Wimmer: Acta Crystallogr., Sect. C 51, 1447 (1995).
F.H. Cano and M. Martinez-Ripoll: J. Mol. Struct. (Theochem) 258, 139 (1992).
F.H. Allen, J.E. Davies, J.J. Galloy, O. Johnson, O. Kennard, C.F. Macrae, E.M. Mitchell, G.F. Mitchell, J.M. Smith, D.G.J. Watson: Chem. Inf. Comput. Sci. 31, 187 (1991).
M.C. Etter: Acc. Chem. Res. 23, 120 (1990).
J. Bernstein, R.E. Davis, L. Shimoni, and N.-L. Chang: Angew. Chem. 107, 1689 (1995); Angew. Chem. Int. Ed. Engl. 34, 1555 (1995).
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Weber, E., Hager, O., Foces-Foces, C. et al. Crystalline Inclusion Compounds Derived from Derivatives of Mandelic Acid. Host Synthesis, Inclusion Formation, and X-Ray Structures of a Free Host Compound and of DMSO Inclusion Complexes in Both Racemic and Optically Resolved Forms. Journal of Inclusion Phenomena 34, 199–220 (1999). https://doi.org/10.1023/A:1008084325792
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DOI: https://doi.org/10.1023/A:1008084325792