Transition from a charge-opposed(+)N-H-N(+) inter-cation hydrogen bonded form of the salt [HN(CH2CH2)3N][OOC(HC=CH) COOH] to the more traditional charge-assisted(+)N-H-O(-) cation-anion hydrogen bonded pseudo-polymorph upon hydration

CrystEngComm

Volumn 6, Issue , 2004, Pages 236-238

  Braga, Dario ^a   Rubini, Katia ^a   Maini, Lucia ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CATION; HYDROGEN; MALEIC ACID; NITROGEN DERIVATIVE; SODIUM CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GRINDING; HUMIDITY; HYDRATION; HYDROGEN BOND; REACTION ANALYSIS;

EID: 12844285496     PISSN: 14668033     EISSN: None     Source Type: Journal    
DOI: 10.1039/b409904b     Document Type: Article

References (30)

1. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, Oxford, 2002.
2. (a) J. Dunitz and J. Bernstein, Acc. Chem. Res., 1995, 28, 193;
3. (b) N. Bladgen and R. J. Davey, Chem. Brit., 1999, 35, 44;
4. (c) R. J. Davey, K. Allen, N. Blagden, W. I. Cross, F. H. Lieberman, M. J. Quayle, S. Righini, L. Seton and G. J. T. Tiddy, CrystEngComm, 2002, 4, 257;
5. (d) R. K. R. Jetti, R. Boese, J. A. R. P. Sarma, L. S. Reddy, P. Vishweshwar and G. R. Desiraju, Angew. Chem. Int. Ed., 2003, 42, 1963;
6. (e) H. G. Brittain, Polymorphism in Pharmaceutical Solids, Marcel Dekker, New York, 1999;
7. (f) A. S. Raw and L. X. Yu, Adv. Drug Delivery Rev., 2004, 56, 235-418 (whole issue).
8. (a) D. Braga, G. R. Desiraju, J. Miller, A. G. Orpen and S. Price, CrystEngComm, 2002, 4, 500;
9. (b) B. Moulton and M. J. Zaworotko, Chem. Rev., 2001, 101, 1629;
10. (c) M. D. Hollingsworth, Science (Washington, D. C.), 2002, 295, 2410;
11. (d) D. Braga, Chem. Commun., 2003, 2751;
12. (e) G. R. Desiraju, Nature (London), 2001, 412, 397.
13. (a) G. W. V. Cave, C. L. Raston and J. L. Scott, Chem. Commun., 2001, 2159;
14. (b) D. Braga and F. Grepioni, Chem. Soc. Rev., 2000, 4, 229;
15. (c) G. Kaupp, CrystEngComm, 2003, 5, 117;
16. (d) T. L. Threlfall, Analyst, 1995, 120, 2435.
17. M. C. Etter, Acc. Chem. Res., 1989, 23, 120.
18. G. Gilli and P. Gilli, J. Mol. Struct., 2000, 552, 1.
19. A. Katrusiak, M. Ratajczak-Sitar and E. Grech, J. Mol. Struct., 1999, 474, 135; Y. J. Kim and J. P. Verkade, Inorg. Chem., 2003, 42, 4262.
20. A. Katrusiak, M. Ratajczak-Sitar and E. Grech, J. Mol. Struct., 1999, 474, 135; Y. J. Kim and J. P. Verkade, Inorg. Chem., 2003, 42, 4262.
21. G. R. Desiraju and T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology. Oxford University Press, Oxford, 1999.
22. The sample of the anhydrous compound was prepared in a glovebag and the sample holder was wrapped with Mylar to prevent the direct contact with air during the measurement. DSC measurements was carried out separately on the anhydrous and hydrated forms (scan speed 5°C min-1, open sample pan). Both forms show an endothermic peak at 151(1)°C followed by an exothermic peak of recrystallization at 153(1)°C.
23. D. Braga and L. Maini, Chem. Commun., 2004, 976.
24. K. F. Bowes, G. Ferguson, A. J. Lough and C. Glidewell, Acta Crystallogr., 2003, B59, 100.
25. A. I. Vogel, Longman, Essex, 1976, p. 596.
26. (a) G. Kaupp and M. Haak, Angew. Chem., Int. Ed. Engl., 1996, 35, 2774;
27. (b) K. Tanaka and F. Toda, Chem. Rev., 2000, 100, 1025;
28. (c) N. J. Coville and D. C. Levendis, Eur. J. Inorg. Chem., 2002, 3067.
29. (a) D. Braga and F. Grepioni, Acc. Chem. Res., 2000, 33, 601;
30. (b) D. Braga, L. Maini, M. Polito and F. Grepioni, Struct. Bond., 2004, 111, 1.