Fine tuning of the cavity size in calixarene-like cyclophanes: A complete series of homooxacalix[4]arene ligands for quaternary ammonium ions

Chemistry - A European Journal

Volumn 4, Issue 10, 1998, Pages 2018-2030

  Masci, Bernardo ^a   Finelli, Marco ^a   Varrone, Maurizio ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Calixarenes; Cyclophanes; Host guest chemistry; Macrocyclic ligands; Quaternary ammonium ions

Indexed keywords

EID: 0031733266     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19981002)4:10<2018::aid-chem2018>3.0.co;2-i     Document Type: Article

References (104)

1. a) F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, England, 1991;
2. b) F. Vögtle, Cyclophane Chemistry - Synthesis, Structures, and Reactions, Wiley, New York, 1993.
3. a) C. D. Gutsche, Calixarenes, Royal Society of Chemistry, Cambridge, England, 1989;
4. b) C. D. Gutsche, in Inclusion Compounds, Vol. 4 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol), Oxford University Press, Oxford, 1991, pp. 27-63;
5. c) C. D. Gutsche, in Large Ring Molecules (Ed.: J. A. Semlyen), Wiley, New York, 1996, pp. 309-343.
6. a) Calixarenes: A Versatile Class of Macrocyclic Compounds (Eds.: J. Vicens, V. Böhmer), Kluwer, Dordrecht, 1991;
7. b) S. Shinkai, Tetrahedron 1993, 49, 8933-8968;
8. c) V. Böhmer, Angew. Chem. 1995, 107, 785-818; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745;
9. c) V. Böhmer, Angew. Chem. 1995, 107, 785-818; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745;
10. d) A. Pochini, R. Ungaro, in Comprehensive Supramolecular Chemistry, Vol. 2 (Ed.: F. Vögtle), Pergamon, Oxford, 1996, pp. 103-142;
11. e) A. Ikeda, S. Shinkai, Chem. Rev. 1997, 97, 1713-1734.
12. a) F. Vögtle, J. Schmitz, M. Nieger, Chem. Ber. 1992, 125, 2523-2531;
13. b) G. Brodesser, F. Vögtle, J. Ind. Phenom. 1994, 19, 111-135.
14. Many of the m-cyclophanes investigated by Tashiro, Yamato, and coworkers formally fall within the class of homocalixarenes. For for some recent papers see, for example: a) T. Yamato, Y. Saruwatari, M. Yasumatsu, J. Chem. Soc. Perkin Trans. 1 1997, 1725-1730; b) T. Yamato, Y. Saruwatari, M. Yasumatsu, J. Chem. Soc. Perkin Trans. 1 1997, 1731-1737; c) T. Yamato, L. K. Doamekpor, H. Tsuzuki, M. Tashiro, Chem. Lett. 1995, 89-90.
15. Many of the m-cyclophanes investigated by Tashiro, Yamato, and coworkers formally fall within the class of homocalixarenes. For for some recent papers see, for example: a) T. Yamato, Y. Saruwatari, M. Yasumatsu, J. Chem. Soc. Perkin Trans. 1 1997, 1725-1730; b) T. Yamato, Y. Saruwatari, M. Yasumatsu, J. Chem. Soc. Perkin Trans. 1 1997, 1731-1737; c) T. Yamato, L. K. Doamekpor, H. Tsuzuki, M. Tashiro, Chem. Lett. 1995, 89-90.
16. Many of the m-cyclophanes investigated by Tashiro, Yamato, and coworkers formally fall within the class of homocalixarenes. For for some recent papers see, for example: a) T. Yamato, Y. Saruwatari, M. Yasumatsu, J. Chem. Soc. Perkin Trans. 1 1997, 1725-1730; b) T. Yamato, Y. Saruwatari, M. Yasumatsu, J. Chem. Soc. Perkin Trans. 1 1997, 1731-1737; c) T. Yamato, L. K. Doamekpor, H. Tsuzuki, M. Tashiro, Chem. Lett. 1995, 89-90.
17. For some polymethylene-bridged methoxymetacyclophanes see also: a) R. B. Bates, S. Gangwar, V. K. Kane, K. Suvannachut, S. R. Taylor, J. Org. Chem. 1991, 56, 1696-1699; b) D. H. Burns, J. D. Miller, J. Santana, J. Org. Chem. 1993, 58, 6526-6528.
18. For some polymethylene-bridged methoxymetacyclophanes see also: a) R. B. Bates, S. Gangwar, V. K. Kane, K. Suvannachut, S. R. Taylor, J. Org. Chem. 1991, 56, 1696-1699; b) D. H. Burns, J. D. Miller, J. Santana, J. Org. Chem. 1993, 58, 6526-6528.
19. C. D. Gutsche, B. Dhawan, J. Org. Chem. 1983, 48, 1536-1539.
20. See, for example: M. Tashiro, A. Tsuge, T. Sawada, T. Makishima, S. Horie, T. Arimura, S. Mataka, T. Yamato, J. Org. Chem. 1990, 55, 2404-2409.
21. a) I. U. Khan, H. Takemura, M. Suenaga, T. Shinmyozu, T. Inazu, J. Org. Chem. 1993, 58, 3158-3161;
22. b) H. Takemura, T. Shinmyozu, H. Miura, I. U. Khan, J. Incl. Phenom. 1994, 19, 189-206;
23. c) P. D. Hampton, W. Tong, S. Wu, E. N. Duesler, J. Chem. Soc. Perkin Trans. 2 1996, 1127-1130.
24. a) P. Zerr, M. Mussrabi, J. Vicens, Tetrahedron Lett. 1991, 32, 1879-1880;
25. b) also the analogous p-methyl-substituted compound had been reported obtained in extremely low yields, see: H. Kämmerer, M. Dahm, Kunstst.-Plast. (Solothurn, Switz.), 1959, 6, 20-26.
26. a) C. Baveaux, F. Vocanson, M. Perrin, R. Lamartine, J. Incl. Phenom. 1995, 22, 119-130;
27. b) P. M. Marcos, J. R. Ascenso, R. Lamartine, J. L. C. Pereira, Supramol. Chem. 1996, 6, 303-306;
28. c) P. M. Marcos, J. R. Ascenso, R. Lamartine, J. L. C. Pereira, Tetrahedron 1997, 53, 11791-11802;
29. d) P. M. Marcos, J. R. Ascenso, R. Lamartine, J. L. C. Pereira, J. Org. Chem. 1998, 63, 69-74;
30. e) I. Dumazet, N. Ehlinger, F. Vocanson, S. Lecocq, R. Lamartine, M. Perrin, J. Incl. Phenom. 1997, 29, 175-185.
31. P. D. Hampton, Z. Bencze, W. Tong, C. E. Daitch, J. Org. Chem. 1994, 59, 4838-4843.
32. a) K. Araki, K. Inada, S. Shinkai, Angew. Chem. 1996, 108, 92-94; Angew. Chem. Int. Ed. Engl. 1996, 35, 72-74;
33. a) K. Araki, K. Inada, S. Shinkai, Angew. Chem. 1996, 108, 92-94; Angew. Chem. Int. Ed. Engl. 1996, 35, 72-74;
34. b) A. Ikeda, M. Yoshimura, S. Shinkai, Tetrahedron Lett. 1997, 38, 2107-2110.
35. G. De Iasi, B. Masci, Tetrahedron Lett. 1993, 34, 6635-6638.
36. B. Masci, S. Saccheo, Tetrahedron 1993, 49, 10739-10748.
37. B. Masci, Tetrahedron 1995, 51, 5459-5464.
38. F. Arnaud-Neu, S. Cremin, D. Cunningham, S. J. Harris, P. McArdle, M. A. McKervey, M. McManus, M.-J. Schwing-Weill, K. Ziat, J. Incl. Phenom. 1991, 10, 329-339.
39. R. M. Izatt, K. Pawlak, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1995, 95, 2529-2586.
40. a) D. A. Stauffer, D. A. Dougherty, Tetrahedron Lett. 1988, 29, 6039-6042;
41. b) M. A. Petti, T. A. Sheppod, R. E. Barrans, Jr., D. A. Dougherty, J. Am. Chem. Soc. 1988, 110, 6825-6840;
42. c) D. A. Dougherty, D. A. Stauffer, Science 1990, 250, 1558-1560.
43. a) A. Collet, J. P Dutasta, B. Lozach, Bull. Soc. Chim. Belg. 1990, 99, 617-633;
44. b) L. Garel, B. Lozach, J.-P. Dutasta, A. Collet, J. Am. Chem. Soc. 1993, 115, 11652-11653.
45. R. Méric, J.-M. Lehn, J.-P. Vigneron, Bull. Soc. Chim. Fr. 1994, 131, 579-583.
46. J. C. Ma, D. A. Dougherty, Chem. Rev. 1997, 97, 1303-1324.
47. Unpublished results obtained in this laboratory.
48. 2 in homothiacalixarenes, and so on) and we simply propose that the numbers should be used which indicate the length of the bridges in naming the cyclophane, that is 1 and 3.3 should have priority with respect to 1, and no further number is needed, since the number of 3 states already indicates the number of oxygen atoms and the overall number of 3 and 1 states already indicates the n value in structure 1. Since cyclophane-bracketed numbers obviously cannot be used within calixarene nomenclature nor, for instance, can compound 8 be indicated as a [3.3.1.1]homooxacalixarene, we provisionally indicate it in the laboratory as a [3.3.1.]homooxacalixphane. A quick identification of the cyclic system will be more and more appreciated on increasing the number of aromatic residues. Manuscripts on large homologues are in preparation.
49. a) B. A. Stochnoff, L. Benoiton, Tetrahedron Lett. 1973, 21-24;
50. b) C. D. Gutsche, B. Dhawan, J. A. Levine, K. H. No, L. J. Bauer, Tetrahedron, 1983, 39, 409-426.
51. Z. Asfari, J. M. Harrowfield, M. I. Ogden, J. Vicens, A. H. White, Angew. Chem. 1991, 103, 887-889; Angew. Chem. Int. Ed. Engl. 1991, 30, 854-856.
52. Z. Asfari, J. M. Harrowfield, M. I. Ogden, J. Vicens, A. H. White, Angew. Chem. 1991, 103, 887-889; Angew. Chem. Int. Ed. Engl. 1991, 30, 854-856.
53. A. Cadogan, D. Diamond, S. Cremin, M. A. McKervey, S. J. Harris, Anal. Proc. 1991, 28, 13-14.
54. Yields obtained from different base-solvent systems have not been checked in the present work.
55. For template effects of alkali metal ions in the formation of macrocyclic polyethers see, for example: a) G. Illuminati, L. Mandolini, B. Masci, J. Am. Chem. Soc. 1983, 105, 555-563; b) L. Mandolini, B. Masci, J. Am. Chem. Soc. 1984, 106, 168-174; c) C. Antonini Vitali, B. Masci, Tetrahedron, 1989, 45, 2213-2222.
56. For template effects of alkali metal ions in the formation of macrocyclic polyethers see, for example: a) G. Illuminati, L. Mandolini, B. Masci, J. Am. Chem. Soc. 1983, 105, 555-563; b) L. Mandolini, B. Masci, J. Am. Chem. Soc. 1984, 106, 168-174; c) C. Antonini Vitali, B. Masci, Tetrahedron, 1989, 45, 2213-2222.
57. For template effects of alkali metal ions in the formation of macrocyclic polyethers see, for example: a) G. Illuminati, L. Mandolini, B. Masci, J. Am. Chem. Soc. 1983, 105, 555-563; b) L. Mandolini, B. Masci, J. Am. Chem. Soc. 1984, 106, 168-174; c) C. Antonini Vitali, B. Masci, Tetrahedron, 1989, 45, 2213-2222.
58. In order to distinguish among the up to three alternate and the up to three partial cone conformations, the aromatic units have been numerated 1-4 starting from the ring containing carbon 1 in calixarene nomenclature, choosing the direction which gives the lowest locants for the oxygen atoms in the macrocycle, and then the lowest locant for the antiparallel unit in the partial cone or for parallel units in alternate conformations (1,4 is preferred to 2,3 in the latter case).
59. 3 signals and the obtained value actually appears to be out of the regular trend.
60. 2Ar carbon atoms.
61. C. Jaime, J. de Mendoza, P. Prados, P. M. Nieto, C. Sanchez, J. Org. Chem. 1991, 56, 3372-3376.
62. a) S. Kanamathareddy, C. D. Gutsche, J. Org. Chem. 1994, 59, 3871-3879;
63. b) D. R. Stewart, M. Krawiec, R. P. Kashyap, W. H. Watson, C. D. Gutsche, J. Am Chem. Soc. 1995, 117, 586-601.
64. Some broadening is actually observed for this signal, possibly due to the presence of a small amount, not directly detected, of other conformers. The signal sharpens again at the lowest attained temperatures, but with a small shift in its position. For other examples of exchange with low-populated conformations see, for example: J. M. Van Gelder, J. Brenn, I. Thondorf, S. Biali, J. Org. Chem. 1997, 62, 3511-3519, and references therein.
65. This conformation is indicated as 1,2-alternate B in ref. [11c].
66. For a discussion of two cases in which the signal is in an intermediate position between δ = 31 and 38, see: J. O. Magrans, J. de Mendoza, M. Pons, P. Prados, J. Org. Chem. 1997, 62, 4518-4520.
67. As can be inferred from ref. [11c].
68. -1 was reported in ref. [11c], although the compound was considered to exist as a mixture of conformations and the process referred to was not indicated.
69. 3 protons).
70. 2Ar protons).
71. -1 in the latter case.
72. -1.
73. C. D. Gutsche, L. J. Bauer, J. Am. Chem. Soc. 1985, 107, 6052-6059.
74. ≠, estimated from the observed rate of exchange, should be corrected for statistical reversion if multistep pathways are followed. The uncertainty due to these factors should not dramatically affect the present comparison.
75. a) L. D. Groenen, J.-D. van Loon, W. Verboom, S. Harkema, A. Casnati, R. Ungaro, A. Pochini, F. Ugozzoli, D. N. Reinhoudt, J. Am. Chem Soc 1991, 113, 2385-2392;
76. b) T. Harada, J. M. Rudzinski, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1992, 2109-2115;
77. c) J. Blixt, C. Detellier, J. Am. Chem. Soc. 1994, 116, 11957-11960.
78. K. Murayama, K. Aoki,J. Chem Soc. Chem. Commun. 1997, 119-120.
79. For an analysis of the mechanisms of molecular recognition see: H.-J. Schneider, Angew. Chem. 1991, 103, 1419-1439; Angew. Chem. Int. Ed. Engl. 1991, 30, 1417-1436.
80. For an analysis of the mechanisms of molecular recognition see: H.-J. Schneider, Angew. Chem. 1991, 103, 1419-1439; Angew. Chem. Int. Ed. Engl. 1991, 30, 1417-1436.
81. Solvent effects on complexation of quaternary ammonium ions by several neutral homooxacalixarene ligands will be dealt with in a forthcoming paper.
82. In such profiles as those in Figures 5 and 6, a homologous series is considered, except for the isomers 8 and 9. For that pair we could consider the property of either compounds or the mean value of the property, when the purely regular structural change should be stressed. We obviously consider both compounds because the plots are merely illustrative, but there is no physical reason to prefer the sequence 7-8-9-10-11 over 7-9-8-10-11.
83. Since the fraction of complexed ligand was actually small in all cases, owing to the relatively low salt concentration and the relative weakness of the complexes, the highest observed effects (ligands 8-11 with TMAP) were in the order of 0.1 ppm. A full quantitative treatment on more suitable ligands will be reported in a forthcoming paper.
84. a) H.-J. Schneider, Recl. Trav. Chim. Pays-Bas 1993, 112, 412-419;
85. b) H.-J. Schneider, V. Rüdiger, U. Cuber, J. Org. Chem. 1995, 60, 996-999, and references therein.
86. ∞ values obtained from the multiparameter fitting procedure have been approximated to 0.01 ppm in Figure 5 and to 0.1 ppm in Table 2.
87. The partial charges in the various positions of the cation should be considered in a less approximated analysis.
88. a) M. Meot-Ner (Mautner), C. A. Deakyne, J. Am. Chem. Soc. 1985, 107, 469-474;
89. b) for very recent ab initio calculations, see: A. Pullman, G. Berthier, R. Savinelli, J. Comput. Chem. 1997, 18, 2012-2022.
90. a) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534;
91. b) C. A. Hunter, Chem. Soc. Rev. 1994, 101-109.
92. In some systems the interaction of homooxacalixarenes with oxygen atoms can be very important. For hydrogen-bonded complexes of primary alkylammonium ions, see ref. [13a].
93. We think, in particular, of the detailed analysis carried out on the important self-assembling systems based on paraquat - aromatic polyethers, as developed by Stoddart and associates; for reviews see: a) D. B. Amabilino, F. M. Raymo, J. F. Stoddart, in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: M. W. Hosseini, J.-P. Sauvage), Pergamon, Oxford, 1996, pp. 85-130; b) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; c) R. E. Gillard, F. M. Raymo, J. F. Stoddart, Chem. Eur. J. 1997, 3, 1933-1940.
94. We think, in particular, of the detailed analysis carried out on the important self-assembling systems based on paraquat - aromatic polyethers, as developed by Stoddart and associates; for reviews see: a) D. B. Amabilino, F. M. Raymo, J. F. Stoddart, in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: M. W. Hosseini, J.-P. Sauvage), Pergamon, Oxford, 1996, pp. 85-130; b) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; c) R. E. Gillard, F. M. Raymo, J. F. Stoddart, Chem. Eur. J. 1997, 3, 1933-1940.
95. We think, in particular, of the detailed analysis carried out on the important self-assembling systems based on paraquat - aromatic polyethers, as developed by Stoddart and associates; for reviews see: a) D. B. Amabilino, F. M. Raymo, J. F. Stoddart, in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: M. W. Hosseini, J.-P. Sauvage), Pergamon, Oxford, 1996, pp. 85-130; b) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; c) R. E. Gillard, F. M. Raymo, J. F. Stoddart, Chem. Eur. J. 1997, 3, 1933-1940.
96. A. Arduini, W. M. McGregor, D. Paganuzzi, A. Pochini, A. Secchi, F. Ugozzoli, R. Ungaro, J. Chem. Soc. Perkin Trans. 2 1996, 839-846.
97. R. Arnecke, V. Böhmer, R. Cacciapaglia, A. Dalla Cort, L. Mandolini, Tetrahedron 1997, 53, 4901-4908.
98. For complexation of related linear alkylammonium cations by calix[5]arenes, see: S. Pappalardo, M. Parisi, J. Org. Chem. 1996, 61, 8724-8725.
99. A. Casnati, P. Iacopozzi, A. Pochini, F. Ugozzoli, R. Cacciapaglia, L. Mandolini, R. Ungaro, Tetrahedron 1995, 51, 591-598.
100. M. Takeshita, S. Nishio, S. Shinkai, J. Org. Chem. 1994, 59, 4032-4034.
101. J. O. Magrans, A. R. Ortiz, M. A. Molins, P. H. P. Lebouille, J. Sánchez-Quesada, P. Prados, M. Pons, F. Gago, J. de Mendoza, Angew. Chem. 1996, 108, 1816-1819; Angew. Chem. Int. Ed. Engl. 1996, 35, 1712-1715.
102. J. O. Magrans, A. R. Ortiz, M. A. Molins, P. H. P. Lebouille, J. Sánchez-Quesada, P. Prados, M. Pons, F. Gago, J. de Mendoza, Angew. Chem. 1996, 108, 1816-1819; Angew. Chem. Int. Ed. Engl. 1996, 35, 1712-1715.
103. F. Hanus, E. Fuchs, J. Prakt. Chem. 1939, 153, 327-336.
104. T. Yamato, L. K. Doamekpor, K. Koizumi, K. Kishi, H. Haraguchi, M. Tashiro, Liebigs Ann. 1995, 1259-1267.