Azonia spiro polyaza macrocycles containing biphenyl subunits as anion and cation receptors

Tetrahedron

Volumn 67, Issue 25, 2011, Pages 4655-4663

  Burguete, M Isabel ^a   Clares, M Paz ^b   García España, Enrique ^b   Luis, Santiago V ^a   Querol, Manel ^a   Martí Centelles, Vicente ^a  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

Anion recognition; Macrocycles; Metal complexes; Polyaza cyclophanes; Supramolecular chemistry

Indexed keywords

ADENOSINE TRIPHOSPHATE; ANION; AZONIA SPIRO POLYAZA MACROCYCLE; BIPHENYL; BIS(CHLOROMETHYL)BIPHENYL; CATION; COPPER; CYCLAM; MACROCYCLIC COMPOUND; NITROGEN; UNCLASSIFIED DRUG; ZINC;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DEPROTECTION REACTION; HYDROGEN BOND; HYDROXYLATION; PH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 79957755391     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.04.071     Document Type: Article

References (115)

1. I.P. Beletskaya, A.D. Averin, A.G. Bessmertnykh, F. Denat, and R. Guilard Russ. J. Org. Chem. 46 2010 947 967
2. J.W. Steed, and J.L. Atwood Supramolecular Chemistry 2nd ed. 2009 John Wiley Hoboken, NJ
3. K. Gloe Macrocyclic Chemistry: Current Trends and Future 2005 Springer Dordrecht
4. J.S. Bradshaw, K.E. Krakowiak, and R.M. Izatt Aza-crown Macrocycles 1993 John Wiley New York, NY
5. C. Bazzicalupi, A. Bencini, A. Bianchi, A. Danesi, E. Faggi, C. Giorgi, S. Santarelli, and B. Valtancoli Coord. Chem. Rev. 252 2008 1052 1068
6. P. Díaz, M. García-Basallote, M.A. Máñez, E. García-España, L. Gil, J. Latorre, C. Soriano, B. Verdejo, and S.V. Luis J. Chem. Soc., Dalton Trans. 2003 1186 1193
7. M.A. Bernardo, F. Pina, B. Escuder, E. García-España, M.L. Godino-Salido, J. Latorre, S.V. Luis, J.A. Ramirez, and C. Soriano J. Chem. Soc., Dalton Trans. 1999 915 921
8. M.A. Bernardo, F. Pina, E. García-España, J. Latorre, S.V. Luis, J.M. Llinares, J.A. Ramirez, and C. Soriano Inorg. Chem. 37 1998 3935 3942
9. A. Andres, C. Bazzicaluppi, A. Bianchi, E. García-España, S.V. Luis, J.F. Miravet, and J.A. Ramirez J. Chem. Soc., Dalton Trans. 1994 2995 3004
10. A. Bencini, A. Bianchi, P. Paoletti, and P. Paoli Coord. Chem. Rev. 120 1992 51 85
11. A. Bianchi, M. Micheloni, and P. Paoletti Coord. Chem. Rev. 110 1991 17 113
12. P. Mateus, N. Bernier, and R. Delgado Coord. Chem. Rev. 254 2010 1726 1747
13. E. García-España, P. Díaz, J.M. Llinares, and A. Bianchi Coord. Chem. Rev. 250 2006 2952 2986
14. S. Sivakova, and S.J. Rowan Chem. Soc. Rev. 34 2005 9 21
15. J.L. Sessler, and J. Jayawickramarajah Chem. Commun. 2005 1939 1949
16. S. Auki, and E. Kimura Chem. Rev. 104 2004 769 787
17. J.M. Llinares, D. Powell, and K. Bowman-James Coord. Chem. Rev. 240 2003 57 75
18. P.D. Beer, and P.A. Gale Angew. Chem., Int. Ed. 40 2001 486 516
19. A. Bianchi, E. García-España, and K. Bowman-James Supramolecular Chemistry of Anions 1997 Wiley-VCH New York, NY
20. See also the recent Supramolecular chemistry of anionic species themed issue: P. Gale, and T. Gunnlaugsson Chem. Soc. Rev. Vol 39 2010 3581 4008
21. F.P. Schmidtchen, and M. Berger Chem. Rev. 97 1997 1609 1646
22. F.P. Schmidtchen Angew. Chem., Int. Ed. Engl. 20 1981 466 468
23. F.P. Schmidtchen Angew. Chem., Int. Ed. Engl. 16 1977 720 721
24. J. Hodacova, J. Aguilar, E. García-España, S.V. Luis, and J.F. Miravet J. Org. Chem. 70 2005 2042 2047
25. Y. Yuan, G. Gao, Z.L. Jiang, J.S. You, Z.Y. Zhou, D.Q. Yuan, and R.G. Xie Tetrahedron 58 2002 8993 8999
26. S.E. Gibson, J.O. Jones, S.B. Kalindjian, J.D. Knight, J.W. Steed, and M.J. Tozer Chem. Commun. 2002 1938 1939
27. M.A. Heuft, and A.G. Fallis Angew. Chem., Int. Ed. 41 2002 4520 4523
28. M.B. Inoue, M. Inoue, R. Sugich-Miranda, L. Machi, E.F. Velazquez, and Q. Fernando Inorg. Chim. Acta 317 2001 181 189
29. A. Andrés, M.I. Burguete, B. Escuder, J.C. Frías, E. García-España, S.V. Luis, and J.F. Miravet J. Org. Chem. 63 1998 1810 1818
30. S. Blasco, M.I. Burguete, M.P. Clares, E. García-España, J. Escorihuela, and S.V. Luis Inorg. Chem. 49 2010 7841 7852
31. M. Bolte, M.I. Burguete, S.V. Luis, I. Alfonso, M. Bru, and J. Rubio J. Am. Chem. Soc. 130 2008 6137 6144
32. M. Bolte, M.I. Burguete, S.V. Luis, I. Alfonso, and M. Bru Chem. - Eur. J. 14 2008 8879 8891
33. I. Alfonso, M.I. Burguete, S.V. Luis, J.F. Miravet, P. Seliger, and E. Tomal Org. Biomol. Chem. 4 2006 853 859
34. M. Bru, M.I. Burguete, S.V. Luis, and I. Alfonso Angew. Chem., Int. Ed. 45 2006 6155 6159
35. F. Galindo, M.I. Burguete, L. Vigara, S.V. Luis, N. Kabir, J. Gavrilovic, and D.A. Russell Angew. Chem., Int. Ed. 44 2005 6504 6508
36. S.V. Luis, F. Galindo, M.I. Burguete, and L. Vigara J. Photochem. Photobiol., A 209 2010 61 67
37. M.I. Burguete, F. Galindo, M.A. Izquierdo, S.V. Luis, and L. Vigara Dalton Trans. 2007 4027 4033
38. F. Galindo, J. Becerril, M.I. Burguete, S.V. Luis, and L. Vigara Tetrahedron Lett. 45 2004 1659 1662
39. M.A. Bernardo, A.J. Parola, F. Pina, E. García-España, S.V. Luis, and J.F. Miravet J. Chem. Soc., Dalton Trans. 1995 993 997
40. B.L. Feringa J. Org. Chem. 72 2007 6635 6652
41. E.R. Kay, D.A. Leigh, and F. Zerbetto Angew. Chem., Int. Ed. 46 2007 72 191
42. W.R. Browne, and B.L. Feringa Nat. Nanotechnol. 1 2006 25 35
43. G.S. Kottas, L.I. Clarke, D. Horinek, and J. Michl Chem. Rev. 105 2005 1281 1376
44. V. Balzani, A. Credi, and M. Venturi Molecular Devices and Machines-A Journey into the Nanoworld 2003 Wiley-VHC Weinheim, Germany
45. J.F. Stoddart Acc. Chem. Res. 34 2001 410 411
46. J.P. Sauvage Molecular Machines and Motors 2001 Springer Berlin
47. A. Harada Acc. Chem. Res. 34 2001 456 464
48. I. Alfonso, M.I. Burguete, F. Galindo, S.V. Luis, and L. Vigara J. Org. Chem. 72 2007 7947 7956
49. I. Alfonso, M.I. Burguete, and S.V. Luis J. Org. Chem. 71 2006 2242 2250
50. M.T. Albelda, M.A. Bernardo, P. Díaz, E. García- España, J. Seixas de Melo, F. Pina, C. Soriano, and S.V. Luis Chem. Commun. 2001 1520 1521
51. M.A. Bernardo, S. Alves, F. Pina, J.S. de Melo, M.T. Albelda, E. García-España, J.M. Llinares, C. Soriano, and S.V. Luis Supramol. Chem. 13 2001 435 445
52. S. Alves, F. Pina, M.T. Albelda, E. García-España, C. Soriano, and S.V. Luis Eur. J. Inorg. Chem. 2001 405 412
53. S.V. Luis, M.I. Burguete, F. Gaviña, A.M. Costero, and J. Rebek Bioorg. Med. Chem. Lett. 1 1991 87 88
54. F. Gaviña, S.V. Luis, A.M. Costero, M.I. Burguete, and J. Rebek J. Am. Chem. Soc. 110 1988 7140 7143
55. J. Rebek Acc. Chem. Res. 17 1984 258 264
56. J. Rebek, R.W. Wattley, T. Costello, R. Gadwood, and L. Marshall J. Am. Chem. Soc. 102 1980 7398 7400
57. K. Brandt, I. Porwolik-Czomperlik, M. Siwy, T. Kupka, R.A. Shaw, D.B. Davies, M.B. Hursthouse, and G.D. Sykara J. Am. Chem. Soc. 119 1997 12432 12440
58. V.M.L.J. Aarts, P.D.J. Grootenhuis, D.N. Reinhoudt, A. Czech, B.P. Czech, and R. Bartsch Recl. Trav. Chim. Pays-Bas 107 1988 94 103
59. S.P. Artz, and D.J. Cram J. Am. Chem. Soc. 106 1984 2160 2171
60. D.N. Reinhoudt, F. de Joy, and M. van de Vondervoot Tetrahedron 37 1981 1985 1990
61. D.N. Reinhoudt, F. de Joy, and M. van de Vondervoot Tetrahedron 37 1981 1753 1762
62. R.C. Helgerson, G.R. Weisman, J.L. Toner, T.L. Tarnowski, Y. Chao, J.M. Mayer, and D.J. Cram J. Am. Chem. Soc. 101 1979 4928 4941
63. H. Kohama, M. Yoshinaga, and K. Ishizu Bull. Chem. Soc. Jpn. 53 1980 3707 3708
64. M.I. Burguete, B. Escuder, E. García-España, L. López, S.V. Luis, J.F. Miravet, and M. Querol Tetrahedron Lett. 43 2002 1817 1819
65. M.I. Burguete, S.V. Luis, J.F. Miravet, M. Querol, and E. García-España Chem. Commun. 1999 649 650
66. A. Montero, F. Albericio, M. Royo, and B. Herradón Eur. J. Org. Chem. 2007 1301 1308
67. K. Choi, and A.D. Hamilton J. Am. Chem. Soc. 125 2003 10241 10249
68. N. Kuhnert, C. Straßnig, and A.M. Lopez-Periago Tetrahedron: Asymmetry 13 2002 123 128
69. A.M. Costero, C. Andreu, R. Martínez-Máñez, J. Soto, L.E. Ochando, and J.M. Amigó Tetrahedron 54 1997 8159 8170
70. H.K. Patel, J.D. Kilburn, G.J. Langley, P.D. Edwards, T. Mitchell, and R. Southgate Tetrahedron Lett. 35 1994 481 484
71. S. Brandes, C. Gros, F. Denat, P. Pullumbi, and R. Guilard Bull. Soc. Chim. Fr. 133 1996 65 73
72. E. García-España, M.J. Ballester, F. Lloret, J.M. Moratal, J. Faus, and A. Bianchi J. Chem. Soc., Dalton Trans. 1988 101 104
73. M. Fontanelli and M. Micheloni, Proceedings of the I Spanish-Italian Congress on Thermodynamics of Metal Complexes, Diputación de Castellón, Spain, 1990. Program for the automatic control of the microburette and the acquisition of the electromotive force readings; Diputación de Castellón.
74. P. Gans, A. Sabatini, and A. Vacca Talanta 43 1996 1739 1753
75. For protonation and complex formation constants for cyclam, see:
76. V.J. Thom, G.D. Hosken, and R.D. Hancock Inorg. Chem. 24 1985 3378 3381
77. M. Micheloni, A., Sabatini, and P. Paoletti J. Chem. Soc., Perkin Trans. 2 1978 828 830
78. J.C. Chambron, and M. Meyer Chem. Soc. Rev. 38 2009 1663 1673
79. Z. Szakacs, M. Kraszni, and B. Noszal Anal. Bioanal. Chem. 378 2004 1428 1448
80. A. Bencini, A. Bianchi, E. Garcia-España, M. Micheloni, and J.A. Ramirez Coord. Chem. Rev. 188 1999 97 156
81. V.J. Aran, M. Kumar, J. Molina, L. Lamarque, P. Navarro, E. Garcia-España, J.A. Ramirez, S.V. Luis, and B. Escuder J. Org. Chem. 64 1999 6135 6146
82. J.A. Aguilar, E. Garcia-España, J.A. Guerrero, S.V. Luis, J.M. Llinares, J.A. Ramirez, and C. Soriano Inorg. Chim. Acta 246 1996 287 294
83. A. Bianchi, B. Escuder, E. Garcia-España, S.V. Luis, V. Marcelino, J.F. Miravet, and J.A. Ramirez J. Chem. Soc., Perkin Trans. 2 1994 1253 1259
84. H. Dong, H. Du, and X. Qian J. Phys. Chem. A 112 2008 12687 12694
85. F. Milletti, L. Storchi, G. Sforna, and G. Cruciani J. Chem. Inf. Model. 47 2007 2172 2181
86. T.N. Brown, and N. Mora-Diez J. Phys. Chem. B 110 2006 20546 20554
87. T.N. Brown, and N. Mora-Diez J. Phys. Chem. B 110 2006 9270 9279
88. M.S. Busch, and E.W. Knapp ChemPhysChem. 5 2004 1513 1522
89. J.A. Pople Gaussian 03, Revision B.04 2003 Gaussian Pittsburgh PA
90. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735 746
91. A.E. Reed, and F. Weinhold J. Chem. Phys. 78 1983 4066 4073
92. J.P. Foster, and F. Weinhold J. Am. Chem. Soc. 102 1980 7211 7218
93. For non-quaternized nitrogen atoms, their involvement in hydrogen bonding is defined when the calculated Wiberg Bond Index (WBI) is greater than 2.95.
94. E. García-España, and S.V. Luis Supramol. Chem. 6 1996 257 266
95. A. Domenech, J.V. Folgado, E. Garcia-España, S.V. Luis, J.M. Llinares, J.F. Miravet, and J.A. Ramirez J. Chem. Soc., Dalton Trans. 1995 541 547
96. A. Andrés, M.I. Burguete, E. García-España, S.V. Luis, J.F. Miravet, and C. Soriano J. Chem. Soc., Perkin Trans. 2 1993 749 754
97. D.K. Chand, H.J. Schneider, J.A. Aguilar, F. Escartí, E. García-España, and S.V. Luis Inorg. Chim. Acta 316 2001 71 78
98. P. Díaz, E. García-España, L. López, S.V. Luis, and M. Querol Supramol. Chem. 2 2002 107 114
99. S. Andres, B. Escuder, A. Domenech, E. Garcia-España, S.V. Luis, V. Marcelino, J.M. Llinares, J.A. Ramirez, and C. Soriano J. Phys. Org. Chem. 14 2001 495 500
100. B. Altava, M.I. Burguete, S.V. Luis, J.F. Miravet, E. Garcia-España, V. Marcelino, and C. Soriano Tetrahedron 53 1997 4751 4762
101. C. Bazzicalupi, A. Bencini, and V. Lippolis Chem. Soc. Rev. 39 2010 3709 3728
102. P. Mateus, R. Delgado, P. Brandão, and V. Félix J. Org. Chem. 74 2009 8638 8646
103. C. Anda, C. Bazzicalupi, A. Bencini, E. Berni, A. Bianchi, P. Fornasari, A. Llobet, C. Giorgi, P. Paoletti, and B. Valtancoli Inorg. Chim. Acta 356 2003 167 178
104. P.D. Beer, J. Cadman, J.M. Lloris, R. Martínez-Máñez, M.E. Padilla, T. Pardo, D.K. Smith, and J. Soto J. Chem. Soc., Dalton Trans. 1999 127 133
105. Q. Lu, J.H. Reibenspies, R.I. Carroll, A.E. Martell, and A. Clearfiled Inorg. Chim. Acta 270 1998 207 215
106. D.A. Nation, J. Reibenspies, and A.E. Martell Inorg. Chem. 35 1996 4597 4603
107. R.J. Motekaitis, and A.E. Martell Inorg. Chem. 31 1992 5534 5542
108. B. Dietrich, J. Guilhem, J.M. Lehn, C. Pascard, and E. Sonveaux Helv. Chim. Acta 67 1984 91 104
109. M.T. Albelda, J. Aguilar, R. Aucejo, P. Díaz, C. Lodeiro, J.C. Lima, E. García-España, F. Pina, and C. Soriano Helv. Chim. Acta 86 2003 3118 3134
110. M.T. Albelda, M.A. Bernardo, E. García-España, M.-L. Godino, S.V. Luis, M.J. Melo, F. Pina, and C. Soriano J. Chem. Soc., Perkin Trans. 2 1999 2545 2549
111. C. Bazzicalupi, A. Bencini, A. Bianchi, M. Cecchi, B. Escuder, V. Fusi, E. García-España, C. Giorgi, S.V. Luis, G. Maccagni, V. Marcelino, P. Paoletti, and B. Valtancoli J. Am. Chem. Soc. 121 1999 6807 6815
112. M.T. Albelda, J.C. Frías, E. García-España, and S.V. Luis J. Chem. Soc., Perkin Trans. 2 2004 816 820
113. Spartan'04; Wavefunction,: Irvine, CA, 2005.
114. F.J. Rossotti, and H. Rossotti J. Chem. Educ. 42 1965 375 378
115. G. Gran Analyst (London) 77 1952 671 681