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Complexation of uncharged molecules and anions by crown-type host molecules

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Host Guest Complex Chemistry I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 98))

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8 References

  1. Saenger, W.: Umschau 74, 635 (1974)

    CAS  Google Scholar 

  2. MacNicol, D. D., McKendrick, J. J., Wilson, D. R.: Chem. Soc. Rev. 7, 65 (1978)

    Article  CAS  Google Scholar 

  3. Mandelcorn, L. (ed.): Non-stoichiometric compounds. New York: Academic Press 1964

    Google Scholar 

  4. Kuhn, H.: Ber. Bunsenges. Phys. Chem. 80, 1209 (1976)

    CAS  Google Scholar 

  5. Frömming, K.-H.: Pharm. in uns. Zeit 2, 109 (1973)

    Google Scholar 

  6. Gawalek, G.: Einschlußverbindungen, Additionsverbindungen, Clathrate. Berlin: VEB Deutscher Verlag der Wissenschaften 1969

    Google Scholar 

  7. Hagan, M.: Clathrate inclusion compounds. New York: Reinhold Publ. Co. 1962

    Google Scholar 

  8. Cramer, F.: Angew. Chem. 64, 437 (1952); 68, 115 (1956); Cramer, F.: Einschlußverbindungen. Berlin, Heidelberg, New York: Springer Verlag 1954; Cramer, F.: Methoden der Organischen Chemie. Houben-Weyl-Müller (eds.), vol. I/1, 4th edit., p. 445. Stuttgart: Georg Thieme Verlag 1958

    Article  CAS  Google Scholar 

  9. Schlenk, W. Jr.,: Chem. in uns. Zeit 3, 120 (1969); Schlenk, Jr., W.: Methoden der Organischen Chemie. Houben-Weyl-Müller (eds.), vol. I/1, 4th edit., p. 391. Stuttgart: Georg Thieme Verlag 1958; Schlenk, Jr., W.: Fortschr. Chem. Forsch. 2, 92 (1951)

    Article  CAS  Google Scholar 

  10. Pollmer, K.: Z. Chem. 19, 81 (1979)

    Article  CAS  Google Scholar 

  11. Davies, J. E. D.: J. Chem. Educ. 54, 536 (1977)

    CAS  Google Scholar 

  12. Hein, F., Heyn, B.: Chemie der Komplexverbindungen. Leipzig: Hirzel Verlag 1978

    Google Scholar 

  13. Pfeiffer, P.: Organische Molekülverbindungen, 2nd edit. Stuttgart: Enke Verlag 1927

    Google Scholar 

  14. Kohler, F., Schneider, G.: Nachr. Chem. Techn. Lab. 25, 381 (1977); see also: Jones, D. S. in Coffey, S. (ed.): Rodd's chemistry of carbon compounds, vol. IV, 2nd ed., part L, p. 186ff. Amsterdam, Oxford, New York: Elsevier Publ. Co. 1980

    Google Scholar 

  15. Foster, R. (ed.): Organic charge-transfer complexes, London: Academic Press 1969; Briegleb, G.: Elektronen-Donator-Acceptor-Komplexe. Berlin, Heidelberg, New York: Springer Verlag 1961; Foster, R. (ed.): Molecular complexes, vols. 1 and 2. London: P. Elek (Scientific Books) Ltd. 1973; Foster, R. (ed.): Molecular association, vol. 1. London: Academic Press 1975; Kover, K. A., Mayer, W.: Pharm. in uns. Zeit 8, 46 (1979)

    Google Scholar 

  16. Vögtle, F.: Chimia 33, 239 (1979)

    Google Scholar 

  17. Vögtle, F.: Pure Appl. Chem. 52, 2405 (1980)

    Google Scholar 

  18. Review: Vögtle, F., Weber, E.: Kontakte (Merck) 1/77, 11; 2/77, 16; 3/77, 36; 2/78, 16; Vögtle, F., Weber, E., Elben, U.: Kontakte (Merck) 3/78, 32; 1/79, 3; 2/80, 36; 1/81, 24. Vögtle, F., Weber, E.: The chemistry of the ether linkage Part II. Patai, S. (ed.), chapter 2, p. 59 ff. New York, London: John Wiley & Sons 1980; Pedersen, C. J., Frensdorff, H. K.: Angew. Chem. 84, 16 (1972); Angew. Chem., Int. Ed. Engl. 11, 16 (1972); Lehn, J. M.: Struct. Bonding 16, 1 (1973); Lehn, J. M.: Pure Appl. Chem. 51, 979 (1979); Lehn, J. M.: Acc. Chem. Res. 11. 49 (1978); Prelog, V.: Pure Appl. Chem. 50, 893 (1978); Cram, D. J., Cram, J. M.: Science 183, 803 (1974); Cram, D. J., Cram, J. M.: Acc. Chem. Res. 11, 8 (1978); Stoddart, J. F.: Chem. Soc. Rev. 8, 85 (1979); Izatt, R. M., Christensen, J. J. (eds.): Synthetic multidentate macrocyclic compounds. New York: Academic Press 1978; Izatt, R. M., Christensen, J. J. (eds.): Progress in macrocyclic chemistry, vol. I. New York: John Wiley and Sons 1979; Bradshaw, J. S. et al.: Chem. Rev. 79, 37 (1979); Bradshaw, J. S., Stott, P. E.: Tetrahedron 36, 461 (1980)

    Google Scholar 

  19. Review: Weber, E., Vögtle, F.: Angew. Chem. 91, 813 (1979); Angew. Chem., Int. Ed. Engl. 18, 753 (1979)

    Article  Google Scholar 

  20. for classification and nomenclature see: Weber, E., Vögtle, F.: Inorg. Chim. Acta 45, L65 (1980)

    Google Scholar 

  21. The definitions complex, adduct, addition compound, molecular compound, molecular complex, associate, inclusion compound, clathrate, host-guest complex, key-lock complex etc. are inconsistently used in the literature. The new term “neutral molecule complex” denotes a complex between two or more uncharged molecules. In contrast, the term “neutral complexes” may designate complexes of e.g. crown ethers with metal salts where the total charge is also zero

    Google Scholar 

  22. Schlenk, Jr., W.: Liebigs Ann. Chem. 1973, 1145

    Google Scholar 

  23. Otto, J.: Acta Crystallogr. B28, 543 (1972)

    Google Scholar 

  24. Schiessler, R. W., Flitter, D.: J. Am. Chem. Soc. 74, 1720 (1952)

    Article  CAS  Google Scholar 

  25. Schlenk, W. Jr.,: Liebigs Ann. Chem. 573, 142 (1951)

    Article  CAS  Google Scholar 

  26. Dianin, A. P.: J. Russ. Phys. Chem. Soc. 46, 1310 (1914); Baker, W., McOmie, J. F. W.: Chem. Ind. (London) 1955, 256

    CAS  Google Scholar 

  27. Collett, A., Jacques, J.: J. Chem. Soc. Chem. Commun. 1976, 708

    Google Scholar 

  28. Gall, J. H. et al.: J. Chem. Soc. Perkin II, 1979, 376

    Google Scholar 

  29. Hardy, A. D. U. et al.: J. Chem. Soc. Chem. Commun. 1977, 292

    Google Scholar 

  30. Flippen, J. L., Karle, J., Karle, I. L.: J. Am. Chem. Soc. 92, 3749 (1970)

    Article  CAS  Google Scholar 

  31. Farina, M., Allegra, G., Natta, G.: J. Am. Chem. Soc. 86, 516 (1964)

    Article  CAS  Google Scholar 

  32. Allegra, G. et al.: J. Chem. Soc. B 1967, 1020

    Google Scholar 

  33. Allegra, G. et al.: J. Chem. Soc. B 1967, 1028

    Google Scholar 

  34. Natta, G., Farina, M.: Struktur und Verhalten von Moelkülen im Raum. Weinheim: Verlag Chemie 1976

    Google Scholar 

  35. Lawton, D., Powell, H. M.: J. Chem. Soc. 1958, 2339; Downing, A. P., Ollis, W. D., Sutherland, I. O.: J. Chem. Soc. B 1970, 24; Brunie, S., Tsoucaris, G.: Cryst. Struct. Commun. 3, 481 (1974); Williams, D. J., Lawton, D.: Tetrahedron Lett. 1975, 111; Baker, W., Gilbert, B., Ollis, W. D.: J. Chem. Soc. 1952, 1443; Arad-Yellin, R. et al.: Tetrahedron Lett. 1980, 387

    Google Scholar 

  36. De Sanctis, S. C. et al.: Acta Crystallogr. B28, 3656 (1972), and references cited therein; Craven, B. M., De Titta, G. T.: J. Chem. Soc. Chem. Commun. 1972, 530

    Google Scholar 

  37. Child, W. C. Jr.,: Quart. Rev. 18, 321 (1964); Powell, H. M.: J. Chem. Soc. 1948, 61; Mark, T. C. W. et al.: J. Chem. Soc. Perkin II, 1976, 1169

    Article  CAS  Google Scholar 

  38. Wong, R. Y. et al.: Acta Crystallogr. B32, 2396 (1976)

    CAS  Google Scholar 

  39. Allemand, A., Gerdil, R.: Acta Crystallogr. A31, s130 (1975)

    Google Scholar 

  40. Allcock, H. R. et al.: J. Am. Chem. Soc. 98, 5120 (1976); Allcock, H. R., Stein, M. T.: J. Am. Chem. Soc. 96, 49 (1974)

    Article  CAS  Google Scholar 

  41. Saenger, W.: Angew. Chem. 92, 343 (1980); Angew. Chem., Int. Ed. Engl. 19, 344 (1980)

    Article  CAS  Google Scholar 

  42. Bender, M. L., Komiyama, M.: Cyclodextrin chemistry. Berlin, Heidelberg, New York: Springer-Verlag 1978

    Google Scholar 

  43. Szejtli, J.: Stärke 30, 427 (1978)

    Article  CAS  Google Scholar 

  44. Bergeron, R. J.: J. Chem. Educ. 54, 204 (1977)

    Article  CAS  Google Scholar 

  45. Saenger, W.: Environmental effects on molecular structure and properties. Pullman, B. (ed.), p. 265ff. Dordrecht, Holland; D. Reidel Publ. Co. 1976

    Google Scholar 

  46. Griffiths, D. W., Bender, M. L.: Adv. Catalysis 23, 209 (1973)

    CAS  Google Scholar 

  47. Cramer, F., Hettler, H.: Naturwiss. 54, 625 (1967)

    Article  CAS  Google Scholar 

  48. Thoma, J. A., Stewart, L.: Starch: Chemistry and technology. Whistler, R. L., Paschall, E. F. (eds.), vol. 1, p. 209. New York: Academic Press 1965

    Google Scholar 

  49. French, D.: Adv. Carbohydr. Chem. 12, 189 (1957)

    CAS  Google Scholar 

  50. Pedersen, C. J.: J. Org. Chem. 36, 1690 (1971)

    Article  CAS  Google Scholar 

  51. Vögtle, F., Müller, W. M.: unpublished results

    Google Scholar 

  52. Knöchel, A. et al.: J. Chem. Soc. Chem. Commun. 1978, 595

    Google Scholar 

  53. McLachland, R. D.: Spectrochim. Acta Vol. A30, 2153 (1974)

    Google Scholar 

  54. Liotta, C. L., Harris, H. P.: J. Am. Chem. Soc. 96, 2250 (1974); Liotta, C. L.: US. Patent 3,997, 562, 1976

    Article  CAS  Google Scholar 

  55. Gokel, G. W. et al.: J. Org. Chem. 39, 2445 (1974)

    Article  CAS  Google Scholar 

  56. Org. Synth. 57, 30 (1977)

    Google Scholar 

  57. Goldberg, I.: Acta Crystallogr. B31, 754 (1975)

    CAS  Google Scholar 

  58. El Basyony, A. et al.: Z. Naturforsch. 31b, 1192 (1976)

    Google Scholar 

  59. Maverick, E. et al.: Acta Crystallogr. B36, 615 (1980)

    CAS  Google Scholar 

  60. Herbert, J. A., Truter, M. R.: Acta Crystallogr. B37 (1981), in press.

    Google Scholar 

  61. Vögtle, F., Müller, W. M., Weber, E.: Chem. Ber. 113, 1130 (1980)

    Article  Google Scholar 

  62. Weber, E., Vögtle, F.: Chem. Ber. 109, 1803 (1976)

    Article  CAS  Google Scholar 

  63. Frensch, K., Oepen, G., Vögtle, F.: Liebigs Ann. Chem. 1979, 858

    Google Scholar 

  64. Vögtle, F., Panagiotidis, I.: unpublished results

    Google Scholar 

  65. Kaufmann, R. et al.: Chem. Ber. 110, 2249 (1977)

    Article  CAS  Google Scholar 

  66. Knöchel, A.: private communication

    Google Scholar 

  67. von Deuten, K. et al.: J. Chem. Res. (S) 1979, 358; (M) 1979, 4035

    Google Scholar 

  68. Chang, C. K.: J. Am. Chem. Soc. 99, 2819 (1977)

    Article  CAS  Google Scholar 

  69. Vögtle, F., Müller, W. M.: Naturwissenschaften 67, 255 (1980)

    Article  Google Scholar 

  70. Vögtle, F., Müller, W. M.: Chem. Ber. 113, 2081 (1980)

    Article  Google Scholar 

  71. Saenger, W., Hilgenfeld, R.: Z. Naturforsch., in press

    Google Scholar 

  72. Shine, H. J.: J. Org. Chem. 24, 252 (1959); Parrick, J., Rasburn, J. W.: Can. J. Chem. 43, 3453 (1965); Hanna, J. G.: The chemistry of the carbonyl group. Patai, S. (ed.), vol. 1, pp. 375, 390. New York, London: Interscience Publishers 1966

    Article  CAS  Google Scholar 

  73. Vögtle, F., Müller, W. M.: Chem. Ber. 114 (1981), in press

    Google Scholar 

  74. Weber, G., Sheldrick, G. M., Acta Crystallogr. 1981, in press. We thank Dr. G. Weber (Univ. Göttingen) for this communication before publication

    Google Scholar 

  75. Review: Truter, M. R.: Struct. Bonding 16, 71 (1973)

    CAS  Google Scholar 

  76. Mercer, M., Truter, M. R.: J. Chem. Soc. Dalton 1973, 2469

    Google Scholar 

  77. Hughes, D. L.: J. Chem. Soc. Dalton 1975, 2374

    Google Scholar 

  78. Hughes, D. L., Wingfield, J. N.: J. Chem. Soc. Chem. Commun. 1977, 80

    Google Scholar 

  79. Christensen, J. J., Eatough, D. J., Izatt, R. M.: Chem. Rev. 74, 351 (1974)

    Article  Google Scholar 

  80. de Jong, F., Reinhoudt, D. N., Smit, C. J.: Tetrahedron Lett. 1976, 1371

    Google Scholar 

  81. Goldberg, I.: Acta Crystallogr. B34, 3387 (1978)

    CAS  Google Scholar 

  82. Helgeson, R. C., Tarnowski, T. L., Cram, D. J.: J. Org. Chem. 44, 2538 (1979)

    Article  CAS  Google Scholar 

  83. Dunitz, J. D., Seiler, P.: Acta Crystallogr. B30, 2739 (1974)

    CAS  Google Scholar 

  84. Mallinson, P. R.: J. Chem. Soc. Perkin Trans. 2, 1975, 266

    Google Scholar 

  85. Newkome, G. R., Fronczek, F. R., Kohli, D. K.: J. Am. Chem. Soc. 103 (1981), in press. Two further crystalline water complexes of coronands containing pyridino ketone units have lately been isolated and studied by X-ray analysis: Newkome, G. R., Vögtle, F. et al., in press.

    Google Scholar 

  86. Frensch, K., Vögtle, F.: Liebigs Ann. Chem. 1979, 2121

    Google Scholar 

  87. Weber, E., Vögtle, F.: Angew. Chem. 92 (1980), 1067; Angew. Chem., Int. Ed. Engl. 19 (1980), 1030

    Article  CAS  Google Scholar 

  88. Shchori, E., Jagur-Grodszinski, J.: Isr. J. Chem. 10, 935 (1972)

    CAS  Google Scholar 

  89. Pannell, K. H., Mayer, A.: J. Chem. Soc. Chem. Commun. 1979, 132

    Google Scholar 

  90. Humphry-Baker, R. et al.: Angew. Chem. 91, 669 (1979); Angew. Chem., Int. Ed. Engl. 18, 630 (1979)

    Article  CAS  Google Scholar 

  91. Dye, J. L.: Angew. Chem. 91, 613 (1979); Angew. Chem., Int. Ed. Engl. 18, 587 (1979)

    Article  CAS  Google Scholar 

  92. Harned, R. L. et al.: Proc. Indiana Acad. Sci. 59, 38 (1959); Steinrauf, L. K., Pinkerton, M., Chamberlin, J. W.: Biochem. Biophys. Res. Commun. 33, 29 (1968)

    Google Scholar 

  93. Brockmann, H., Schmidt-Kastner, G.: Chem. Ber. 88, 57 (1955); Pinkerton, M., Steinrauf, L. K., Dawkins, P.: Biochem. Biophys. Res. Commun. 35, 512 (1969)

    Article  CAS  Google Scholar 

  94. Raßhofer, W., Vögtle, F.: Tetrahedron Lett. 1978, 309

    Google Scholar 

  95. Wendt, B., Ried, W.: Angew. Chem. 63, 218 (1951)

    Article  CAS  Google Scholar 

  96. Cf. also: Weber, E., Vögtle, F.: Tetrahedron Lett. 1975, 2415

    Google Scholar 

  97. Vögtle, F., Sieger, H.: Angew. Chem. 89, 410 (1977); Angew. Chem., Int. Ed. Engl. 16, 396 (1977)

    Article  Google Scholar 

  98. Suh, I.-H., Saenger, W.: Angew. Chem. 90, 565 (1978); Angew. Chem. Int. Ed. Engl. 17, 534 (1978)

    Article  CAS  Google Scholar 

  99. Weber, G., Saenger, W.: Acta Crystallogr. B36, 424 (1980)

    CAS  Google Scholar 

  100. Saenger, W. et al.: Metal-ligand interactions in organic chemistry and biochemistry. Pullman, B., Goldblum, W. (eds.), p. 363. Dordrecht, Holland: D. Reidel Publ. Co. 1977

    Google Scholar 

  101. Saenger, W., Brand, H.: Acta Crystallogr. B35, 838 (1979)

    CAS  Google Scholar 

  102. Heimann, U., Vögtle, F.: Chem. Ber. 112, 3034 (1979)

    Article  CAS  Google Scholar 

  103. Vögtle, F., Oepen, G., Raßhofer, W.: Liebigs Ann. Chem. 1979, 1577

    Google Scholar 

  104. Newcomb, M., Gokel, G. W., Cram, D. J.: J. Am. Chem. Soc. 96, 6810 (1974); Newcomb, M. et al.: J. Am. Chem. Soc. 99, 6392 (1977)

    Article  CAS  Google Scholar 

  105. Oepen, G., Vögtle, F.: Liebigs Ann. Chem. 1980, 512

    Google Scholar 

  106. Saenger, W.: private communication

    Google Scholar 

  107. Hayward, R. C.: Nachr. Chem. Techn. Lab. 25, 15 (1977)

    Google Scholar 

  108. Lutz, W. K., Winkler, F. K., Dunitz, J. D.: Helv. Chim. Acta 54, 1103 (1971)

    Article  CAS  Google Scholar 

  109. Agtarap, A. et al.: J. Am. Chem. Soc. 89, 5737 (1967)

    Article  CAS  Google Scholar 

  110. Pinkerton, M., Steinrauf, L. K.: J. Mol. Biol. 49, 533 (1970)

    Article  CAS  Google Scholar 

  111. Lutz, W. K., Wipf, H.-K., Simon, W.: Helv. Chim. Acta 53, 1741 (1970)

    Article  CAS  Google Scholar 

  112. Lindenbaum, S., Sternson, L., Rippel, S.: J. Chem. Soc. Chem. Commun. 1977, 268

    Google Scholar 

  113. Hodgson, K. O.: Intra-Sci. Chem. Rept. 8, 27 (1974)

    CAS  Google Scholar 

  114. Burgermeister, W., Winkler-Oswatitsch, R.: Top. Curr. Chem. 69, 91 (1977)

    Article  CAS  Google Scholar 

  115. Agtarap, A., Chamberlin, J. N.: Antimicrob. Agents Chemotherap. 1967, 359; see also: Collum, D. B., McDonald, III., J. H., Still, W. C.: J. Am. Chem. Soc. 102, 2117 (1980)

    Google Scholar 

  116. Kubota, T. et al.: J. Chem. Soc. Chem. Commun. 1968, 1541; Shiro, M., Koyama, H.: J. Chem. Soc. B 1970, 243

    Google Scholar 

  117. Weber, G., Saenger, W.: Acta Crystallogr. B36, 207 (1980)

    Google Scholar 

  118. Mootz, D., Wussow, H. G.: Angew. Chem. 92, 559 (1980); Angew. Chem., Int. Ed. Engl. 19, 552 (1980): In the pyridine 2.5 H2O complex the water molecules form a hydrogen-bridged separate layer, some hydrogen bridges binding to the nitrogen atoms of the pyridine rings in another layer

    Article  CAS  Google Scholar 

  119. Oepen, G., J. P. Dix, Vögtle, F.: Liebigs Ann. Chem. 1978, 1592; b) Saenger, W. (MPI Göttingen): private communication

    Google Scholar 

  120. Vögtle, F. et al.: Angew. Chem. 89, 564 (1977); Angew. Chem., Int. Ed. Engl. 16, 548 (1977)

    Article  Google Scholar 

  121. Weber, G., Sheldrick, G. M.: Acta Crystallogr. B36, 1978 (1980). Crystal structure of the RbI complex: Weber, G., Sheldrick, G. M.: Inorg. Chim. Acta 45, L35 (1980)

    CAS  Google Scholar 

  122. Dunitz, D. J. et al.: Acta Crystallogr. B30, 2733 (1974)

    CAS  Google Scholar 

  123. Fries, J., Getrost, H.: Organische Reagentien für die Spurenanalyse (E. Merck, Darmstadt), 1975

    Google Scholar 

  124. Pfeiffer, P., Tappermann, F.: Z. Anorg. Allg. Chem. 215, 273 (1933)

    Article  CAS  Google Scholar 

  125. Pfeiffer, P., Werdelmann, B.: Z. Anorg. Allg. Chem. 261, 197 (1950)

    CAS  Google Scholar 

  126. Pfeiffer, P., Christeleit, W.: Z. Anorg. Allg. Chem. 239, 133 (1938)

    Article  CAS  Google Scholar 

  127. Buhleier, E., Vögtle, F.: Liebigs Ann. Chem. 1977, 1080

    Google Scholar 

  128. Vögtle, F., Müller, W. M., Raßhofer, W.: Isr. J. Chem. 18, 246 (1979)

    Google Scholar 

  129. Gillard, R. D., Johns, K. W., Williams, P. A.: J. Chem. Soc. Chem. Commun. 1979, 357

    Google Scholar 

  130. Summers, L. A.: Advances in heterocyclic chemistry. Vol. 22. New York, San Francisco, London: Academic Press, 1978

    Google Scholar 

  131. Oepen, G., Vögtle, F.: Liebigs Ann. Chem. 1979, 2114

    Google Scholar 

  132. We thank Prof. Dr. W. H. Watson, Texas Christian University, for this communication before publication

    Google Scholar 

  133. Vögtle, F., Weber, E.: Angew. Chem. 86, 896 (1974); Angew. Chem., Int. Ed. Engl. 13, 814 (1974)

    Article  Google Scholar 

  134. MacNicol, D. D., Wilson, D. R.: J. Chem. Soc. Chem. Commun. 1976, 494

    Google Scholar 

  135. Baker, H. J.: Rec. Trav. Chim. Pays-Bas 54, 833 (1935)

    Google Scholar 

  136. Baker, H. J.: Rec. Trav. Chim. Pays-Bas 54, 905 (1935)

    Google Scholar 

  137. Baker, H. J.: Rec. Trav. Chim. Pays-Bas 55, 17 (1936)

    Google Scholar 

  138. Hardy, A. D. U., MacNicol, D. D., Wilson, D. R.: J. Chem. Soc. Perkin II 1979, 1011

    Google Scholar 

  139. MacNicol, D. D., Hardy, A. D. U., Wilson, D. R.: Nature 266, 611 (1977)

    Article  CAS  Google Scholar 

  140. Cp. structure of hexakis (2-bromomethyl) benzene: Marsau, M. P.: Acta Crystallogr. 18, 851 (1965)

    Article  CAS  Google Scholar 

  141. Baker, H. J.: Rec. Trav. Chim. Pays-Bas 54, 745 (1935)

    Google Scholar 

  142. MacNicol, D. D., Wilson, D. R.: Chem. Ind. (London) 1977, 84

    Google Scholar 

  143. MacNicol, D. D., Swanson, S.: J. Chem. Res. (S) 1979, 406

    Google Scholar 

  144. Freer, A. et al.: Tetrahedron Lett. 1980, 205

    Google Scholar 

  145. Freer, A. et al.: Tetrahedron Lett. 1980, 1159

    Google Scholar 

  146. Weber, E., Müller, W. M., Vögtle, F.: Tetrahedron Lett. 1979, 2335

    Google Scholar 

  147. Stetter, H., Roos, E.-E.: Chem. Ber. 88, 1390 (1955)

    Article  CAS  Google Scholar 

  148. Faust, G., Pallas, M.: J. prakt. Chem. 11, 146 (1960)

    Article  CAS  Google Scholar 

  149. Cf. the toluene complex of a tetrahydroxy [1.1.1.1]metacyclophane host molecule: Andreetti, G. D., Ungaro, R., Pochini, A.: Chem. Commun. 1979, 1005

    Google Scholar 

  150. Odashima, K. et al.: J. Am. Chem. Soc. 102, 2504 (1980); Odashima, K. et al.: Tetrahedron Lett. 1980, 4347; Soga, T., Odashima, K., Koga, K.: Tetrahedron Lett. 1980, 4351

    Article  CAS  Google Scholar 

  151. Benesi, H. A., Hildebrand, J. H.: J. Am. Chem. Soc. 71, 2703 (1949)

    Article  CAS  Google Scholar 

  152. Jarvi, E. T., Whitlock, H. W. Jr.,: J. Am. Chem. Soc. 102, 657 (1980)

    Article  CAS  Google Scholar 

  153. Almog, J. et al.: J. Am. Chem. Soc. 97, 226 (1975); Almog, J., Baldwin, J. E., Huff, J.: J. Am. Chem. Soc. 97, 227 (1975)

    Article  CAS  Google Scholar 

  154. Jameson, D. B., Evers, J. A.: J. Am. Chem. Soc. 102, 2823 (1980)

    Article  CAS  Google Scholar 

  155. Park, C. H., Simmons, H. E.: J. Am. Chem. Soc. 90, 2431 (1968)

    Article  CAS  Google Scholar 

  156. Bell, R. A. et al.: Science 190, 151 (1975)

    CAS  Google Scholar 

  157. Tabushi, I., Sasaki, H., Kuroda, Y.: J. Am. Chem. Soc. 98, 5727 (1976); Tabushi, I., Kuroda, Y., Kimura, Y.: Tetrahedron Lett. 1976, 3327

    Article  CAS  Google Scholar 

  158. Cf. kinetic studies for the protonation of cryptands: Cox, B. G., Knop, D., Schneider, H.: J. Am. Chem. Soc. 100, 6002 (1978)

    Article  CAS  Google Scholar 

  159. Graf, E., Lehn, J. M.: J. Am. Chem. Soc. 98, 6403 (1976), ibid. 97, 5022 (1975)

    Article  CAS  Google Scholar 

  160. Cf. also cyclodextrin anion complexes: Wojcik, J. F., Rohrbach, R. P.: J. Phys. Chem. 79, 2251 (1975); Rohrbach, R. P. et al.: J. Phys. Chem. 81, 944 (1977)

    Article  CAS  Google Scholar 

  161. Schmidtchen, F. P.: Angew. Chem. 89, 751 (1977); Angew. Chem., Int. Ed. Engl. 16, 720 (1977); Chem. Ber. 113, 864 (1980)

    Article  CAS  Google Scholar 

  162. Lehn, J. M., Sonveaux, E., Willard, A. K.: J. Am. Chem. Soc. 100, 4914 (1978); see also Lehn, J. M. et al.: J. Am Chem. Soc. 103, 1282 (1981)

    Article  CAS  Google Scholar 

  163. Dietrich, B. et al.: J. Chem. Soc. Chem. Commun. 1978, 934

    Google Scholar 

  164. Dietrich, B. et al.: Helv. Chim. Acta 62, 2763 (1979)

    Article  CAS  Google Scholar 

  165. Coughlin, P. K. et al.: J. Am. Chem. Soc. 101, 265 (1979)

    Article  CAS  Google Scholar 

  166. Fee, J. A., Briggs, R. G.: Biochem. Biophys. Acta 400, 439 (1975)

    CAS  Google Scholar 

  167. Drew, M. G. B., McCann, M., Nelson, S. M.: J. Chem. Soc. Chem. Commun. 1979, 481

    Google Scholar 

  168. Agnus, Y., Louis, R., Weiss, R.: J. Am. Chem. Soc. 101, 3381 (1979)

    Article  CAS  Google Scholar 

  169. Wester, N., Vögtle, F.: Chem. Ber. 113, 1487 (1980)

    Article  CAS  Google Scholar 

  170. Rossa, L., Vögtle, F.: Liebigs Ann. Chem. 1981, 459

    Google Scholar 

  171. Hilgenfeld, R., Saenger, W.: 6th European Crystallographic Meeting, Barcelona, Spain 1980; Angew. Chem. 93, 1981, in press

    Google Scholar 

  172. Myskiv, M. G.: Proceedings of the 12th International Congress on Crystallography, Warsaw 1978

    Google Scholar 

  173. van Bergen, T. J., Kellogg, R. M.: J. Am. Chem. Soc. 99, 3882 (1977); Kellogg, R. M.: J. Chem. Soc. Chem. Commun. 1978, 923

    Article  Google Scholar 

  174. Herbert, J. A., Truter, M. R.: J. Chem. Soc. Perkin II 1980, 1253

    Google Scholar 

  175. Lehn, J. M.: Pure Appl. Chem. 50, 871 (1978)

    CAS  Google Scholar 

  176. Bhagwat, V. W., Manohar, H., Poonia, N. S.: Inorg. Nucl. Chem. Lett. 16, 289 (1980)

    Article  CAS  Google Scholar 

  177. Weber, E.: Angew. Chem. 91, 230 (1979); Angew. Chem., Int. Ed. Engl. 18, 219 (1979)

    Article  CAS  Google Scholar 

  178. Czugler, M., Weber, E.: J. Chem. Soc. Chem. Commun. 1981, 472

    Google Scholar 

  179. Raßhofer, W., Müller, W. M., Vögtle, F.: Chem. Ber. 112, 2095 (1979)

    Article  Google Scholar 

  180. Czugler, M.: private communication

    Google Scholar 

  181. Singh, T. P., Reinhoudt, N., Poonia, N. S.: Inorg. Nucl. Chem. Lett. 16, 239 (1980)

    Google Scholar 

  182. Suh, I. et al.: Z. Naturforsch. 35b, 352 (1980)

    CAS  Google Scholar 

  183. Vögtle, F., Herzhoff, M.: unpublished results

    Google Scholar 

  184. Vögtle, F., Müller, W. M.: Angew. Chem. 91, 676 (1979); Angew. Chem., Int. Ed. Engl. 18, 623 (1979)

    Article  Google Scholar 

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Vögtle, F., Sieger, H., Müller, W.M. (1981). Complexation of uncharged molecules and anions by crown-type host molecules. In: Host Guest Complex Chemistry I. Topics in Current Chemistry, vol 98. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0111247

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  • DOI: https://doi.org/10.1007/BFb0111247

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