Endo-complexation of alkylammonium ions by calix[4]arene cavity: Facilitating cation-π interactions through the weakly coordinating anion approach

Journal of Organic Chemistry

Volumn 79, Issue 20, 2014, Pages 9842-9846

  Talotta, Carmen ^a   Gaeta, Carmine ^a   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLAMMONIUM; ALKYLAMMONIUM IONS; BIOLOGICAL RECEPTORS; CALIX[4]ARENES; H-BONDING INTERACTION; P-TERT-BUTYLCALIX[4]ARENE; TRIFLUOROMETHYL; WEAKLY COORDINATING ANIONS;

POSITIVE IONS;

ALKYLAMMONIUM ION; AMMONIA; CALIX[4]ARENE; CATION; MACROCYCLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; ANION; BORIC ACID; CALIX(4)ARENE; CALIXARENE; FLUORINATED HYDROCARBON; PHENOL DERIVATIVE; TETRAKIS(3,5-BIS(TRIFLUOROMETHYL)PHENYL)BORATE; TETRYLAMMONIUM;

ARTICLE; CHEMICAL INTERACTION; COMPLEX FORMATION; HYDROGEN BOND; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY; SURFACE PROPERTY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY;

ANIONS; BORATES; CALIXARENES; HYDROCARBONS, FLUORINATED; HYDROGEN BONDING; MOLECULAR STRUCTURE; PHENOLS; TETRAETHYLAMMONIUM;

EID: 84908225615     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5016689     Document Type: Article

References (44)

1. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vogtle, F., Eds.; Pergamon Press: New York, 1996.
2. Jefferey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: Oxford, 1997.
3. (a) Dougherty, D. A. Acc. Chem. Res. 2013, 46, 885-893.
4. (b) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
5. (a) Xiu, X.; Puskar, N. L.; Shanata, J. A. P.; Lester, H. A.; Dougherty, D. A. Nature 2009, 458, 534-538.
6. (b) Celie, P. H.; Van Rossum-Fikkert, S. E.; Van Dijk, W. J.; Brejc, K.; Smit, A. B.; Sixma, T. K. Neuron 2004, 41, 907-914.
7. (c) Tavares Da Silva, X.; Blum, A. P.; Nakamura, D. T.; Puskar, N. L.; Shanata, J. A. P.; Lester, H. A.; Dougherty, D. A. J. Am. Chem. Soc. 2012, 134, 11474-11480.
8. Aleshin, A. E.; Stoffer, B.; Firsov, L. M.; Svensson, B.; Honzatko, R. B. Biochemistry 1996, 35, 8319-8328.
9. (a) Miles, T. F.; Bower, K. S.; Lester, H. A.; Dougherty, D. A. ACS Chem. Neurosci. 2012, 3, 753-760.
10. (b) Duffy, N. H.; Lester, H. A.; Dougherty, D. A. ACS Chem. Biol. 2012, 7, 1738-1745.
11. (a) Gutsche, C. D. Calixarenes, An Introduction; Royal Society of Chemistry: Cambridge, UK, 2008.
12. (b) Arnaud-Neu, F.; Fuangswasdi, S.; Notti, A.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 112-114.
13. (c) Parisi, M. F.; Pappalardo, S. J. Org. Chem. 1996, 61, 8724-8725.
14. (d) Capici, C.; Cohen, Y.; D'Urso, A.; Gattuso, G.; Notti, A.; Pappalardo, A.; Pappalardo, S.; Parisi, M. F.; Purrello, R.; Slovak, S.; Villari, V. Angew. Chem., Int. Ed. 2011, 50, 11956-11961.
15. (e) Capici, C.; Gattuso, G.; Notti, A.; Parisi, M. F.; Pappalardo, S.; Brancatelli, G.; Geremia, S. J. Org. Chem. 2012, 77, 9668-9675.
16. (f) Coquière, D.; de la Lande, A.; Martì, S.; Parisel, O.; Prangé, T.; Reinaud, O. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 10449-10454.
17. (g) Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2010, 12, 2092-2095.
18. (h) Gaeta, C.; Talotta, C.; Farina, F.; Camalli, M.; Campi, G.; Neri, P. Chem. - Eur. J. 2012, 18, 1219-1230.
19. (i) Gaeta, C.; Talotta, C.; Farina, F.; Teixeira, F. A.; Marcos, P. A.; Ascenso, J. R.; Neri, P. J. Org. Chem. 2012, 77, 10285-10293.
20. (j) Talotta, C.; Gaeta, C.; Qi, Z.; Schalley, C. A.; Neri, P. Angew. Chem., Int. Ed. 2013, 52, 7437-7441.
21. (k) Gaeta, C.; Talotta; Neri, P. Chem. Commun. 2014, 50, 9917-9920.
22. (a) Fan, J.; Chen, Y.; Cao, D.; Yang, Y.-W.; Jia, X.; Li, C. RSC Adv. 2014, 4, 4330-4333.
23. (b) Li, C.; Shu, X.; Li, J.; Fan, J.; Chen, Z.; Weng, L.; Jia, X. Org. Lett. 2012, 14, 4126-4129.
24. Gokel, G. W. Crown Ethers and Cryptands: Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1991.
25. (a) Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844-4870.
26. (b) Tootoonchi, H. M.; Yi, S.; Kaifer, A. E. J. Am. Chem. Soc. 2013, 135, 10804-10809.
27. (c) Kim, Y.; Kim, H.; Ko, Y. H.; Selvapalam, N.; Selvapalam, N.; Rekharsky, M. V.; Inouew, Y.; Kim, K. Chem. - Eur. J. 2009, 15, 6143-6151.
28. (d) Mock, W.; Shih, N. Y. J. Am. Chem. Soc. 1986, 51, 4440-4446.
29. See the Supporting Information for further details.
30. (GAUSSIAN 09 Software Package).
31. (a) Hirose, K. Analytical Methods. In Analytical Methods in Supramolecular Chemistry; Schalley, C. A., Eds.; WILEY-VCH: Weinheim, 2007; Chapter 2, pp 17-54.
32. (b) Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311-312.
33. Mecozzi, S.; West, A. P.; Dougherty, D. A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10566-10571.
34. Chen, N.-C.; Chuang, C.-J.; Wang, L.-Y.; Lai, C.-C.; Chiu, S.-H. Chem. - Eur. J. 2012, 18, 1896-1890
35. Han, C.; Gao, L.; Yu, G.; Zhang, Z.; Dong, S.; Huang, F. Eur. J. Org. Chem., 2013, 2529-2532.
36. Gasa, T. B.; Cory Valente, C.; Stoddart, J. F. Chem. Soc. Rev. 2011, 40, 57-78 and references cited therein.
37. (a) Gattuso, G.; Notti, A.; Pappalardo, A.; Parisi, M. F.; Pisagatti, I.; Pappalardo, S.; Garozzo, D.; Messina, A.; Cohen, Y.; Slovak, S. J. Org. Chem. 2008, 73, 7280-7289.
38. (b) Brancatelli, G.; Gattuso, G.; Geremia, S.; Notti, A.; Pappalardo, S.; Parisi, M. F.; Pisagatti, I. Org. Lett. 2014, 16, 2354-2357 and references cited therein.
39. Körner, S. K.; Tucci, F. C.; Rudkevich, D. M.; Heinz, T.; Rebek, J., Jr. Chem. - Eur. J. 2000, 6, 187-195.
40. Cohen, Y.; Avram, L.; Frish, L. Angew. Chem., Int. Ed. 2005, 44, 520-554.
41. (a) Nishida, H.; Takada, N.; Yoshimura, M.; Sonoda, T.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1984, 57, 2600-2604.
42. (b) Ikeda, A.; Nagasaki, T.; Araki, K.; Shinkai, S. Tetrahedron 1992, 48, 1059-1070.
43. Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
44. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc.: Wallingford, CT, 2009.