Conformational features and recognition properties of a conformationally blocked calix[7]arene derivative

Chemistry - A European Journal

Volumn 18, Issue 4, 2012, Pages 1219-1230

  Gaeta, Carmine ^a   Talotta, Carmen ^a   Farina, Francesco ^a   Campi, Gaetano ^b   Camalli, Mercedes ^b   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b CNR   (Italy)

Author keywords

calixarenes; conformational analysis; host guest systems; molecular recognition; structure elucidation

Indexed keywords

ACID DERIVATIVE; ALKALI CATIONS; ALKYLAMMONIUM; AMMONIUM CATIONS; ARENE DERIVATIVES; BORATE ANIONS; CALIXARENES; CHEMICAL SHIFT SURFACES; CONFORMATIONAL ANALYSIS; CONTOUR PLOT; DEGREE OF SIMILARITY; HOST-GUEST SYSTEM; MACROCYCLES; RECOGNITION ABILITIES; RECOGNITION PROPERTIES; STRUCTURE ELUCIDATION; TETRAKIS; THEORETICAL STRUCTURE; TRIFLUOROMETHYL; X-RAY STRUCTURE;

AMMONIUM COMPOUNDS; CHEMICAL ANALYSIS; CHEMICAL SHIFT; CONFORMATIONS; MOLECULAR RECOGNITION; PHENOLS; POSITIVE IONS;

FEATURE EXTRACTION;

EID: 84855966749     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102179     Document Type: Article

References (79)

1. C. D. Gutsche, Calixarenes - An Introduction, 2 nd ed., The Royal Society of Chemistry, Cambridge, 2008
2. V. Böhmer, Angew. Chem. 1995, 107, 785-818
3. Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745
4. A. Ikeda, S. Shinkai, Chem. Rev. 1997, 97, 1713-1734.
5. Calixarenes 2001 (Eds.:, Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens,), Kluwer, Dordrecht, 2001
6. Calixarenes in the Nanoworld (Eds.:, J. Vicens, J. Harrowfield,), Springer, Dordrecht, 2006.
7. I. Columbus, S. E. Biali, Org. Lett. 2007, 9, 2927-2929
8. K. Kogan, S. E. Biali, Org. Lett. 2007, 9, 2393-2396
9. L. Kuno, S. Noa, S. E. Biali, Org. Lett. 2007, 9, 1577-1580; for the introduction of oxygenated functions into the calix walls, see
10. C. Gaeta, F. Troisi, M. Martino, E. Gavuzzo, P. Neri, Org. Lett. 2004, 6, 3027-3030
11. F. Troisi, L. Mogavero, C. Gaeta, E. Gavuzzo, P. Neri, Org. Lett. 2007, 9, 915-918
12. F. Troisi, L. Citro, C. Gaeta, E. Gavuzzo, P. Neri, Org. Lett. 2008, 10, 1393-1396
13. C. Gaeta, F. Troisi, E. Gavuzzo, M. Camalli, G. Campi, P. Neri, CrystEngComm 2010, 12, 880-887
14. C. Gaeta, F. Troisi, R. Spagna, M. Camalli, G. Campi, P. Neri, CrystEngComm 2011, 13, 467-473; a novel approach to functionalize the calixarene exo rim with nucleophiles using calixarene p-bromodienone derivatives has been recently reported
15. F. Troisi, T. Pierro, C. Gaeta, P. Neri, Org. Lett. 2009, 11, 697-700
16. F. Troisi, T. Pierro, M. Carratà, C. Gaeta, P. Neri, Tetrahedron Lett. 2009, 50, 4416-4419
17. C. Gaeta, M. Martino, P. Neri, Tetrahedron Lett. 2003, 44, 9155-9159; for an analogous procedure in which alkoxy groups are introduced into the calixarene exo rim, starting from calixarene spirodienone derivatives, see
18. S. Thulasi, G. V. Bhagavathy, J. Eliyan, L. R. Varma, Tetrahedron Lett. 2009, 50, 770-772.
19. A. Arduini, A. Pochini, A. Secchi, F. Ugozzoli, in Calixarenes 2001 (Eds.:, Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens,), Kluwer, Dordrecht, 2001, pp. 457-475, for recent examples, see
20. S. Lea Gac, M. Luhmer, O. Reinaud, I. Jabin, Tetrahedron 2007, 63, 10721-10730
21. D. Coquière, J. Marrot, O. Reinaud, Org. Biomol. Chem. 2008, 6, 3930-3934
22. D. Coquière, S. Lea Gac, U. Darbost, O. Sénèque, I. Jabin, O. Reinaud, Org. Biomol. Chem. 2009, 7, 2485-2500
23. C. Monnereau, J.-N. Rebilly, O. Reinaud, Eur. J. Org. Chem. 2011, 166-175.
24. S. E. Matthews, P. D. Beer, in Calixarenes 2001 (Eds.:, Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens,), Kluwer, Dordrecht, 2001, pp. 421-439; for recent examples, see
25. F. Troisi, A. Russo, C. Gaeta, G. Bifulco, P. Neri, Tetrahedron Lett. 2007, 48, 7986-7989
26. F. Troisi, C. Gaeta, T. Pierro, P. Neri, Tetrahedron Lett. 2009, 50, 5113-5115
27. T. Pinter, S. Jana, R. J. M. Courtemanche, F. Hof, J. Org. Chem. 2011, 76, 3733-3741.
28. L. Gregoli, L. Russo, I. Stefio, C. Gaeta, F. Arnaud-Neu, V. Hubscher-Bruder, P. Khazaeli-Parsa, C. Geraci, P. Neri, Tetrahedron Lett. 2004, 45, 6277-6281
29. E. Wanigasekara, C. Gaeta, P. Neri, D. M. Rudkevich, Org. Lett. 2008, 10, 1263-1266
30. T. Pierro, C. Gaeta, F. Troisi, P. Neri, Tetrahedron Lett. 2009, 50, 350-353
31. T. Pierro, C. Gaeta, P. Neri, Supramol. Chem. 2010, 22, 726-736
32. S. Moerkerke, M. Ménand, I. Jabin, Chem. Eur. J. 2010, 16, 11712-11719.
33. For a review on the chemistry of calix[7]arenes, see:, M. Martino, P. Neri, Mini-Rev. Org. Chem. 2004, 1, 219-231.
34. M. Martino, L. Gregoli, C. Gaeta, P. Neri, Org. Lett. 2002, 4, 1531-1534.
35. M. Martino, C. Gaeta, L. Gregoli, P. Neri, Tetrahedron Lett. 2002, 43, 9521-9525.
36. M. Martino, C. Gaeta, P. Neri, Tetrahedron Lett. 2004, 45, 3387-3391.
37. Z. Luo, S. Gong, C. Zhang, Q. Zheng, Y. Chen, Synlett 2006, 5, 795-797.
38. H. Li, D. Xiong, Y. Chen, P. Xie, J. Wan, J. Inclusion Phenom. Macrocyclic Chem. 2008, 60, 169-172.
39. C. Gaeta, T. Caruso, M. Mincolelli, F. Troisi, E. Vasca, P. Neri, Tetrahedron 2008, 64, 5370-5378.
40. L. Erra, C. Tedesco, G. Vaughan, M. Brunelli, F. Troisi, C. Gaeta, P. Neri, CrystEngComm 2010, 12, 3463-3466.
41. C. Gaeta, F. Troisi, P. Neri, Org. Lett. 2010, 12, 2092-2095
42. C. Talotta, C. Gaeta, T. Pierro, P. Neri, Org. Lett. 2011, 13, 2098-2101
43. T. Pierro, C. Gaeta, C. Talotta, A. Casapullo, P. Neri, Org. Lett. 2011, 13, 2650-2653.
44. S. H. Strauss, Chem. Rev. 1993, 93, 927-942
45. H. Nishida, N. Takada, M. Yoshimura, T. Sonoda, H. Kobayashi, Bull. Chem. Soc. Jpn. 1984, 57, 2600-2604; for recent examples on the use of TFPB superweak anion in supramolecular chemistry, see
46. B. A. Blight, A. Camara-Campos, S. Djurdjevic, M. Kaller, D. A. Leigh, F. M. McMillan, H. McNab, A. M. Slawin, J. Am. Chem. Soc. 2009, 131, 14116-14122
47. H. Hou, K. C.-F. Leung, D. Lanari, A. Nelson, J. F. Stoddart, R. H. Grubbs, J. Am. Chem. Soc. 2006, 128, 15358-13359; for a review on counterion effects in supramolecular chemistry, see
48. T. B. Gasa, C. Valente, J. F. Stoddart, Chem. Soc. Rev. 2011, 40, 57-78.
49. F. Cunsolo, M. Piattelli, P. Neri, J. Chem. Soc. Chem. Commun. 1994, 1917-1918
50. F. Cunsolo, G. M. L. Consoli, M. Piattelli, P. Neri, Tetrahedron Lett. 1996, 37915-918
51. C. Geraci, M. Piattelli, G. Chessari, P. Neri, J. Org. Chem. 2000, 65, 5143-5151.
52. C. Gaeta, M. Martino, L. Gregoli, P. Neri, Tetrahedron Lett. 2002, 43, 8875-8878.
53. T. Harada, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1995, 2231.
54. C. Geraci, G. Chessari, M. Piattelli, P. Neri, Chem. Commun. 1997, 921-922
55. G. M. L. Consoli, F. Cunsolo, C. Geraci, E. Gavuzzo, P. Neri, Org. Lett. 2002, 4, 2649-2652.
56. P. Neri, G. M. L. Consoli, F. Cunsolo, C. Geraci, M. Piattelli, in Calixarenes 2001 (Eds.:, Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens,), Kluwer, Dordrecht, 2001, 5, pp.89- 109.
57. G. D. Andreetti, F. Ugozzoli, Y. Nakamoto, S.-I. Ishida, J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 10, 241-253
58. M. Perrin, S. Lecocq, Z. Asfari, C. R. Acad. Sci. Ser. 2 1990, 310, 515-520
59. P. Thuéry, M. Nierlich, M. I. Ogden, J. M. Harrowfield, Supramol. Chem. 1998, 9, 297-303
60. P. Thuéry, M. Nierlich, B. Souley, Z. Asfari, J. Vicens, J. Chem. Soc. Dalton Trans. 1999, 2589-2594
61. J. L. Atwood, M. J. Hardie, C. L. Raston, C. A. Sandoval, Org. Lett. 1999, 1, 1523-1526
62. R. Ludwig, D. Lentz, T. K. D. Nguyen, Radiochim. Acta 2000, 88, 335-343.
63. G. Bifulco, L. Gomez-Paloma, R. Riccio, C. Gaeta, F. Troisi, P. Neri, Org. Lett. 2005, 7, 5757-5760
64. G. Bifulco, R. Riccio, C. Gaeta, P. Neri, Chem. Eur. J. 2007, 13, 7185-7194.
65. C. D. Gutsche, Calixarenes, Royal Society of Chemistry, Cambridge, 1989, pp. 110-111
66. S. Kanamathareddy, C. D. Gutsche, J. Org. Chem. 1992, 57, 3160-3166
67. C. Jaime, J. dea Mendoza, P. Prados, P. M. Nieto, C. Sanchez, J. Org. Chem. 1991, 56, 3372-3376
68. J. O. Magrans, J. dea Mendoza, M. Pons, P. Prados, J. Org. Chem. 1997, 62, 4518-4520.
69. K. B. Lipkowitz, G. Pearl, J. Org. Chem. 1993, 58, 6729-6736.
70. Molecular modeling was performed with the MacroModel-9.0/Maestro-4.1 program:, F. Mohamadi, N. G. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
71. F. Ugozzoli, G. D. Andreetti, J. Inclusion Phenom. Mol. Recognit. Chem. 1992, 13, 337-348.
72. K. Hirose, in Analytical Methods in Supramolecular Chemistry (Ed.:, C.A. Schalley,), Wiley-VCH, Weinheim, 2007, pp. 17-54.
73. Y. Tanaka, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 1990, 112, 2807-2808.
74. F. Arnaud-Neu, S. Fuangswasdi, A. Notti, S. Pappalardo, M. F. Parisi, Angew. Chem. 1998, 110, 120-122
75. Angew. Chem. Int. Ed. Engl. 1998, 37, 112-114.
76. Compound 1 was prepared according to the acid-catalyzed one-pot procedure described in:, D. R. Stewart, C. D. Gutsche, J. Am. Chem. Soc. 1999, 121, 4136-4146.
77. M. Colapietro, G. Cappuccio, C. Marciante, A. Pifferi, R. Spagna, J. R. Helliwell, J. Appl. Crystallogr. 1992, 25, 192-194.
78. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. Dea Caro, C. Giacovazzo, G. Polidori, D. Siliqi, R. Spagna, J. Appl. Crystallogr. 2007, 40, 609-613.
79. S. Braun, H.-O. Kalinowsky, S. Berger, 150 and More Basic NMR Experiments: A Practical Course, Wiley-VCH, Weinheim, 1996, pp. 232-233.