Hydrogen bonds in radical cation salts of TTF(CH2OH) 4: First complete series with the octahedral rhenium cluster anions [Re6S8-nCl6+n]n-4 (n = 0, 1, 2, 3)

Crystal Growth and Design

Volumn 5, Issue 4, 2005, Pages 1585-1596

  Perruchas, Sandrine ^a,b   Boubekeur, Kamal ^a,c   Batail, Patrick ^a,d  

^a INSTITUT DES MATÉRIAUX JEAN ROUXEL   (France)

^b Department of Obstetrics Gynecology   (United States)

^c CNRS   (France)

^d UNIVERSITÉ D'ANGERS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 22744438350     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg0500573     Document Type: Article

References (69)

1. (a) Opalovskii, A. A.; Fedorov, V. E.; Lobkov, E. U. Russ. J. Inorg. Chem. 1971, 16, 790.
2. (b) Leduc, L.; Perrin, A.; Sergent, M. C. R. Acad. Sci. Paris, Ser. 2 1983, 296, 961.
3. Gabriel, J. C.; Boubekeur, K.; Uriel, S.; Batail, P. Chem. Rev. 2001, 101, 2037-2066.
4. Batail, P.; Ouahab, L.; Pénicaud, A.; Lenoir, C.; Perrin, A. C. R. Acad. Sci. 1987, 304, 1111-1116.
5. Pénicaud, A.; Lenoir, C.; Batail, P.; Coulon, C.; Perrin, A. Synth. Met. 1989, 32, 25-32.
6. Batail, P.; Boubekeur, K.; Fourmigué, M.; Dolbecq, A.; Gabriel, J.-C.; Guirauden, A.; Livage, C.; Uriel, S. New J. Chem. 1994, 18, 999-1006.
7. (a) Pénicaud, A.; Boubekeur, K.; Batail, P.; Canadell, E.; Auban-Senzier, P. J. Am. Chem. Soc. 1993, 115, 4101-4112.
8. (b) Deluzet, A.; Rousseau, R.; Guilbaud, C.; Granger, I.; Boubekeur, K.; Batail, P.; Canadell, E.; Auban-Senzier, P.; Jérome, D. Chem. Eur. J. 2002, 8, 3884-3900.
9. (a) Batail, P.; Livage, C.; Parkin, S. S. P.; Coulon, C.; Martin, J. D.; Canadell, E. Angew. Chem., Int. Ed. Engl. 1991, 30, 1498-1500.
10. (b) Coulon, C.; Livage, C.; Gonzalez, L.; Boubekeur, K.; Batail, P. J. Phys. I 1993, 1153-1174.
11. (c) Boubekeur, K. Ph.D. Thesis, Université de Rennes, 1989.
12. Dolbecq, A.; Boubekeur, K.; Batail, P.; Canadell, E.; Auban-Senzier, P.; Coulon, C.; Lerstrup, K.; Bechgaard, K. J. Mater. Chem. 1995, 5, 1707-1718.
13. Deluzet, A.; Batail, P.; Misaki, Y.; Auban-Senzier, P.; Canadell, E. Adv. Mater. 2000, 12, 436-439.
14. Boubekeur, K.; Lenoir, C.; Batail, P.; Carlier, R.; Tallec, A.; Le Paillard, M.-P.; Lorcy, D.; Robert, A. Angew. Chem., Int. Ed. Engl. 1994, 33, 1379-1381.
15. Renault, A.; Lajzerowicz, J.; Batail, P.; Coulon, C. Bull. Soc. Chim. France 1993, 130, 740-744.
16. Dolbecq, A.; Fourmigué, M.; Krebs, F. C.; Batail, P.; Canadell, E.; Clérac, R.; Coulon, C. Chem. Eur. J. 1996, 2, 1275-1282.
17. (a) Heuzé, K.; Fourmigué, M.; Batail, P.; Canadell, E.; Auban-Senzier, P. Chem. Eur. J. 1999, 5, 2971-2976.
18. (b) Heuzé, K.; Mézière, C.; Fourmigué, M.; Batail, P.; Coulon, C.; Canadell, E.; Auban-Senzier, P.; Jérome, D. Chem. Mater. 2000, 12, 1898-1904.
19. (c) Heuzé, K.; Fourmigué, M.; Batail, P.; Coulon, C.; Clérac, R.; Canadell, E.; Auban-Senzier, P.; Ravy, S.; Jérome, D. Adv. Mater. 2003, 15, 1251-1254.
20. (d) Baudron, S. A.; Mézière, C.; Heuzé, K.; Fourmigué, M.; Batail, P.; Molinié, P.; Auban-Senzier, P. J. Solid State Chem. 2002, 168, 668-674.
21. (e) Baudron, S. A.; Avarvari, N.; Batail, P.; Coulon, C.; Clérac, R.; Canadell, E.; Auban-Senzier, P. J. Am. Chem. Soc. 2003, 125, 11583-11590.
22. (f) Baudron, S. A.; Batail, P.; Rovira, C.; Canadell, E.; Clérac, R. Chem. Commun. 2003, 1820-1821.
23. (g) Devic, T.; Avarvari, N.; Batail, P. Chem. Eur. J. 2004, 10, 3696-3707.
24. (h) Ono, G.; Terao, H.; Higuchi, S.; Sugarawa, T.; Izuoka, A.; Mochida, T. J. Mater. Chem. 2000, 10, 2277-2282.
25. Moore, A. J.; Bryce, M. R.; Batsanov, A. S.; Heaton, J. N.; Lehmann, C. W.; Howard, J. A. K.; Robertson, N.; Underhill, A. E.; Perepichka, I. F. J. Mater. Chem. 1998, 8, 1541-1550.
26. (a) Morita, Y.; Maki, S.; Ohmoto, M.; Kitagawa, H.; Okubo, T.; Mitani, T.; Nakasuji, K. Org. Lett. 2002, 4, 2185-2188.
27. (b) Neilands, O.; Belyakov, S.; Tilika, V.; Edzina, A. Chem. Commun. 1995, 325-326.
28. Murata, T.; Morita, Y.; Fukui, K.; Sato, K.; Shiomi, D.; Takui, T.; Maesato, M.; Yamochi, H.; Saito, G.; Nakasuji, K. Angew. Chem., Int. Ed. 2004, 43, 6343-6346.
29. (a) Blanchard, P.; Boubekeur, K.; Sallé, M.; Duguay, G.; Jubault, M.; Gorgues, A.; Martin, J. D.; Canadell, E.; Auban-Senzier, P.; Jérome, D.; Batail, P. Adv. Mater. 1992, 4, 579-581.
30. (b) Dolbecq, A.; Fourmigué, M.; Batail, P.; Coulon, C. Chem. Mater. 1994, 6, 1413-1418.
31. (c) Dolbecq, A.; Guirauden, A.; Fourmigué, M.; Boubekeur, K.; Batail, P.; Rhomer, M.-M.; Bénard, M.; Coulon, C.; Sallé, M.; Blanchard, P. J. Chem. Soc., Dalton Trans. 1999, 1241-1248.
32. (d) Legros, J.-P.; Dahan, F.; Binet, L.; Fabre, J.-M. Synth. Met. 1999, 102, 1632-1633.
33. (e) Legros, J.-P.; Dahan, F.; Binet, L.; Carcel, C.; Fabre, J.-M. J. Mater. Chem. 2000, 10, 2685-2691.
34. (f) Yao, Y.; Zeng, W.; Zhang, B.; Liu, Y.; Zhu, D. Acta Cryst 2000, C56, e90-e91.
35. (g) Li, H.; Zhang, D.; Zhang, B.; Yao, Y.; Xu, W.; Zhu, D.; Wang, Z. J. Mater. Chem. 2000, 10, 2063-2067.
36. (h) Liu, S.-X.; Neels, A.; Stoeckli-Evans, H.; Pilkington, M.; Wallis, J. D.; Decurtins, S. Polyhedron 2004, 23, 1185-1189.
37. Fourmigué, M.; Batail, P. Chem. Rev. 2004, 104, 5379-5418.
38. Sallé, M.; Gorgues, A.; Jubault, M.; Boubekeur, K.; Batail, P. Tetrahedron 1992, 48, 3081-3090.
39. Fox, M. A.; Pan, H. J. Org. Chem. 1994, 59, 6519-6527.
40. Gabriel, J.-C.; Boubekeur, K.; Batail, P. Inorg. Chem. 1993, 32, 2894-2900.
41. Uriel, S.; Boubekeur, K.; Gabriel, J.-C.; Batail, P.; Orduna, J. Bull. Soc. Chim. Fr. 1996, 133, 783-794.
42. Guilbaud, C.; Gabriel, J.-C.; Boubekeur, K.; Batail, P. C. R. Acad. Sci. IIc 1998, 765-770.
43. Long, J.; McCarthy, L. S.; Holm, R. H. J. Am. Chem. Soc. 1996, 118, 4603-4616.
44. Cotton, F. A.; Wing, R. M.; Zimmerman, A. Inorg. Chem. 1967, 6, 11-15.
45. (a) Montgomery, L. K. Organic Conductors, Fundamentals and Applications; Farges, J.-P., Ed.; Dekker: New York, 1994, 115-145.
46. (b) Batail, P.; Boubekeur, K.; Fourmigué, M.; Gabriel, J.-C. P. Chem. Mater. 1998, 10, 3005-3015.
47. Stoe-IPDS Software manual V2.87, December 1997, STOE, Darmstadt, Germany.
48. Sheldrick, G. M. University of Gottingen, 1997.
49. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76.
50. Steiner, T.; Saenger, W. Acta Crystallogr. 1992, B48, 819-827.
51. Hoffmann, R. J. Chem. Phys. 1963, 39, 1397-1412.
52. Ammeter, J. H.; Bürgi, H.-B.; Thibeault, J.; Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 3686-3692.
53. Mori, T. Bull. Chem. Soc. Jpn. 1998, 71, 2509-2526.
54. Dautel, O.; Fourmigué, M. J. Org. Chem. 2000, 65, 6479-6486.
55. (a) Mallik, A. B.; Lee, S.; Tran, L.; Lobkovsky, E. B. Cryst. Growth Des. 2003, 3, 467-473.
56. (b) Xu, Z.; Kiang, Y.-H.; Lee, S.; Lobkovsky, E. B. J. Am. Chem. Soc. 2000, 122, 8376-8391.
57. Etter, M. Acc. Chem. Res. 1990, 23, 120-126.
58. Guilbaud, C.; Deluzet, A.; Domercq, B.; Molinié, P.; Coulon, C.; Boubekeur, K.; Batail, P. Chem. Commun. 1999, 1867-1868.
59. Guilbaud, C. Ph.D. Thesis, Université de Nantes, 1998.
60. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford Press University, Oxford, 1997.
61. Novoa, J. J.; Nobeli, I.; Grepioni, F.; Braga, D. New J. Chem. 2000, 24, 5-8.
62. Jeffrey, G. A.; Mitra, J. Acta Crystallogr. 1983, B39, 469-480.
63. (a) Aullon, G.; Bellamy, D.; Brammer, L.; Bruton, E. A.; Orpen, A. G. Chem. Commun. 1998, 653-654.
64. (b) Brammer, L.; Bruton, E. A.; Sherwood, P. Cryst. Growth Des. 2001, 1, 277-290.
65. Steiner, T. Acta Crystallogr. 1998, B54, 456-463. Note that mean O⋯Cl distances is this work are slightly longer. The values reported in this reference are limited to O-H⋯Cl angles higher than 140°, which are usually associated with short O⋯Cl distances and then strong O-H⋯Cl hydrogen bonds.
66. Dautel, O. J.; Fourmigué, M.; Canadell, E. Chem. Eur. J. 2001, 7, 2635-2643.
67. Deluzet, A.; Duclusaud, H.; Sautet, P.; Borshch, S. Inorg. Chem. 2002, 41, 2537-2542.
68. Yap, G. P. A.; Rheingold, A. L.; Das, P.; Crabtree, R. H. Inorg. Chem. 1995, 34, 3474-3476.
69. Uriel, S.; Boubekeur, K.; Batail, P.; Orduna, J.; Canadell, E. Inorg. Chem. 1995, 34, 5307-5313.