Crystallographic evidence of nitrate-π interactions involving the electron-deficient 1,3,5-triazine ring

Inorganic Chemistry

Volumn 45, Issue 17, 2006, Pages 6637-6645

  Maheswari, Palanisamy Uma ^a   Modec, Barbara ^b   Pevec, Andrej ^b   Kozlevčar, Bojan ^b   Massera, Chiara ^c   Gamez, Patrick ^a   Reedijk, Jan ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

^c UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ACETONITRILE DERIVATIVE; HYDROGEN; NITRATE; OXYGEN; TRIAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; METABOLISM; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ACETONITRILES; CRYSTALLOGRAPHY, X-RAY; ELECTRONS; HYDROGEN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRATES; OXYGEN; STEREOISOMERISM; TRIAZINES;

EID: 33748612965     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic060101j     Document Type: Article

References (52)

1. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210-1250.
2. Egli, M.; Tereshko, V.; Mushudov, G. N.; Sanishvili, R.; Liu, X. Y.; Lewis, F. D. J. Am. Chem. Soc. 2003, 125, 10842-10849.
3. Gallivan, J. P.; Dougherty, D. A. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 9459-9464.
4. Scrutton, N. S.; Raine, A. R. C. Biochem. J. 1996, 319, 1-8.
5. Vilar, R. Angew. Chem., Int. Ed. 2003, 42, 1460-1477.
6. Garau, C.; Quinonero, D.; Frontera, A.; Ballester, P.; Costa, A.; Deya, P. M. New J. Chem. 2003, 27, 211-214.
7. Kubik, S.; Reyheller, C.; Stuwe, S. J. Inclusion Phenom. Macrocycl. Chem. 2005, 52, 137-187.
8. Mangani, S.; Ferraroni, M. Supramolecular Chemistry of Anions; Wiley: New York, 1997; pp 63-78.
9. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 487-516.
10. Sessler, J. L.; Katayev, E.; Pantos, G. D.; Scherbakov, P.; Reshetova, M. D.; Khrustalev, V. N.; Lynch, V. M.; Ustynyuk, Y. A. J. Am. Chem. Soc. 2005, 127, 11442-11446.
11. Bowman-James, K. Acc. Chem. Res. 2005, 38, 671-678.
12. Coombs, N. D.; Aldridge, S.; Wiltshire, G.; Kays, D. L.; Bresner, C.; Ooi, L. L. J. Organomet. Chem. 2005, 690, 2725-2731.
13. Antonisse, M. M. G.; Snellink-Ruel, B. H. M.; Yigit, I.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1997, 62, 9034-9038.
14. Alkorta, I.; Rozas, I.; Elguero, J. J. Org. Chem. 1997, 62, 4687-4691.
15. Garau, C.; Frontera, A.; Quinonero, D.; Ballester, P.; Costa, A.; Deya, P. M. ChemPhysChem 2003, 4, 1344-1348.
16. Quinonero, D.; Garau, C.; Rotger, C.; Frontera, A.; Ballester, P.; Costa, A.; Deya, P. M. Angew. Chem., Int. Ed. 2002, 41, 3389-3392.
17. Quinonero, D.; Garau, C.; Frontera, A.; Ballester, P.; Costa, A.; Deya, P. M. Chem. Phys. Lett. 2002, 359, 486-492.
18. Quinonero, D.; Garau, C.; Frontera, A.; Ballester, P.; Costa, A.; Deya, P. M. J. Phys. Chem. A 2005, 109, 4632-4637.
19. Mascal, M.; Armstrong, A.; Bartberger, M. D. J. Am. Chem. Soc. 2002, 124, 6274-6276.
20. Garau, C.; Quinonero, D.; Frontera, A.; Costa, A.; Ballester, P.; Deya, P. M. Chem. Phys. Lett. 2003, 370, 7-13.
21. Kim, D.; Tarakeshwar, P.; Kim, K. S. J. Phys. Chem. A 2004, 108, 1250-1258.
22. Schneider, H. J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417-1436.
23. Schneider, H. J.; Blatter, T.; Palm, B.; Pfingstag, U.; Rudiger, V.; Theis, I. J. Am. Chem. Soc. 1992, 114, 7704-7708.
24. Schneider, H. J.; Werner, F.; Blatter, T. J. Phys. Org. Chem. 1993, 6, 590-594.
25. Demeshko, S.; Dechert, S.; Meyer, F. J. Am. Chem. Soc. 2004, 126, 4508-4509.
26. Gamez, P.; Reedijk, J. Eur. J. Inorg. Chem. 2006, 29-42.
27. Gamez, P.; de Hoog, P.; Lutz, M.; Spek, A. L.; Reedijk, J. Inorg. Chim. Acta 2003, 351, 319-325.
28. de Hoog, P.; Gamez, P.; Driessen, W. L.; Reedijk, J. Tetrahedron Lett. 2002, 43, 6783-6786.
29. de Hoog, P.; Gamez, P.; Mutikainen, H.; Turpeinen, U.; Reedijk, J. Angew. Chem., Int. Ed. 2004, 43, 5815-5817.
30. de Hoog, P.; Gamez, P.; Roubeau, O.; Lutz, M.; Driessen, W. L.; Spek, A. L.; Reedijk, J. New J. Chem. 2003, 27, 18-21.
31. Gamez, P.; de Hoog, P.; Roubeau, O.; Lutz, M.; Driessen, W. L.; Spek, A. L.; Reedijk, J. Chem. Commun. 2002, 1488-1489.
32. Sheldrick, G. M. SHELXS97. Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1997.
33. Sheldrick, G. M. SHELXL97. Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
34. SAINT, Software Users Guide, 6.0; Bruker Analytical X-ray Systems: Madison, WI, 1999.
35. Sheldrick, G. M. SADABS Area-Detector Absorption Correction, 2.03; University of Göttingen: Göttingen, Germany, 1999.
36. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119.
37. Nardelli, M. J. Appl. Crystallogr. 1996, 29, 296-300.
38. Spek, A. L. PLATON, A Multi-Purpose Cristallographic Tool; Utrecht University: Utrecht, The Netherlands, 2003.
39. Møller, C.; Plesset, M. Phys. Rev. 1934, 618-622.
40. Headgordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503-506.
41. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; 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.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
42. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
43. Simon, S.; Duran, M.; Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024-11031.
44. CINECA: Consorzio Interuniversitario per il Calcolo Automatico dell'Italia Nord Orientale, v. M., 40033 Casalecchio di Reno (Bo), Italy.
45. Arranz-Mascaros, P.; Lopez-Garzon, R.; Gutierrez-Valero, M. D.; Godino-Salido, M. L.; Moreno, J. M. Inorg. Chim. Acta 2000, 304, 137-143.
46. Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349-1356.
47. Schottel, B. L.; Chifotides, H.; Shatruk, M.; Chouai, A.; Pérez, L. M.; Bacsa, J.; Dunbar, K. R. J. Am. Chem. Soc. 2006, 128, 5895-5912.
48. Garau, C.; Quinonero, D.; Frontera, A.; Ballester, P.; Costa, A.; Deya, P. M. J. Phys. Chem. A 2005, 109, 9341-9345.
49. Amoedo-Portela, A.; Carballo, R.; Casas, J. S.; Garcia-Martinez, E.; Lago-Blanco, A. B.; Sanchez-Gonzalez, A.; Sordo, J.; Vazquez-Lopez, E. M. Z. Anorg. Allg. Chem. 2005, 631, 2241-2246.
50. Comba, P.; de Laorden, C. L.; Pritzkow, H. Helv. Chim. Acta 2005, 88, 647-664.
51. Beghidja, A.; Hallynek, S.; Welter, R.; Rabu, P. Eur. J. Inorg. Chem. 2005, 662-669.
52. Garau, C.; Quinonero, D.; Frontera, A.; Ballester, P.; Costa, A.; Deya, P. M. Org. Lett. 2003, 5, 2227-2229.