Hydrogen bonding and dynamic behaviour in crystals and polymorphs of dicarboxylic-diamine adducts: A comparison between NMR parameters and X-ray diffraction studies

Chemistry - A European Journal

Volumn 11, Issue 24, 2005, Pages 7461-7471

  Gobetto, Roberto ^a   Nervi, Carlo ^a   Chierotti, Michele R ^a   Braga, Dario ^b   Maini, Lucia ^b   Grepioni, Fabrizia ^b   Harris, Robin K ^c   Hodgkinson, Paul ^c  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Hydrogen bonds; NMR spectroscopy; Polymorphism; Relaxation times; Supramolecular chemistry

Indexed keywords

AMINES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; RELAXATION PROCESSES; SALTS; SINGLE CRYSTALS; SUPRAMOLECULAR CHEMISTRY; X RAY DIFFRACTION ANALYSIS;

POLYMORPHISM; RELAXATION TIMES;

HYDROGEN BONDS;

EID: 29144498345     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500616     Document Type: Article

References (78)

1. W. C. McCrone, Polymorphism in Physics and Chemistry of the Organic Solid State (Eds.: D. Fox, M. M. Labes, A. Weissenberger), Interscience, New York, 1965.
2. T. L. Threlfall, Analyst 1995, 120, 2435-2460.
3. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, Oxford, 2002.
4. J. Bernstein, R. J. Davey, J. O. Henck, Angew. Chem. 1999, 111, 3646-3669;
5. Angew. Chem. Int. Ed. 1999, 38, 3440-3461.
6. J. D. Dunitz, J. Bernstein, Acc. Chem. Res. 1995, 25, 193-200.
7. D. Braga, F. Grepioni, Chem. Soc. Rev. 2000, 29, 229-238.
8. R. J. Davey, K. Allen, N. Blagden, W. I. Cross, H. F. Lieberman, M. J. Quayle, S. Righini, L. Seton, G. J. T. Tiddy, CrystEngComm 2002, 4, 257-264.
9. D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen, S. L. Price, CrystEngComm 2002, 4, 500-509.
10. B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629-1658.
11. M. D. Hollingsworth, Science 2002, 295, 2410-2413.
12. D. Braga, Chem. Commun. 2003, 2751-2754.
13. G. R. Desiraju, Nature 2001, 412, 397-400.
14. L. Brammer, Chem. Soc. Rev. 2004, 33, 476-489.
15. M. W. Hosseini, CrystEngComm 2004, 6, 318-322.
16. N. Blagden, R. Davey, Chem. Br. 1999, 35, 44-47.
17. N. Blagden, R. J. Davey, Cryst. Growth Des. 2003, 3, 873-885.
18. R. K. R. Jetti, R. Boese, J. A. R. P. Sarma, L. S. Reddy, P. Vishweshwar, G. R. Desiraju, Angew. Chem. 2003, 115, 2008-2012;
19. Angew. Chem. Int. Ed. 2003, 42, 1963-1967.
20. P. Erk, H. Hengelsberg, M. F. Haddow, R. van Gelder, CrystEngComm 2004, 6, 474-483.
21. N. Shan, F. Toda, W. Jones, Chem. Commun. 2002, 2372-2373.
22. A. V. Trask, N. Shan, W. D. S. Motherwell, W. Jones, S. H. Feng, R. B. H. Tan, K. J. Carpenter, Chem. Commun. 2005, 880-882.
23. A. V. Trask, W. D. S. Motherwell, W. Jones, Chem. Commun. 2004, 890-891.
24. D. Braga, F. Grepioni, Angew. Chem. 2004, 116, 4092-4102;
25. Angew. Chem. Int. Ed. 2004, 43, 4002-4011.
26. G. Gilli, P. Gilli, J. Mol. Struct. 2000, 552, 1-15.
27. T. Steiner, Angew. Chem. 2002, 114, 50-80;
28. Angew. Chem. Int. Ed. 2002, 41, 48-76.
29. D. Braga, L. Maini, M. Polito, F. Grepioni, Hydrogen Bonding Interactions Between Ions: A Powerful Tool in Molecular Crystal Engineering, Springer, Berlin, 2004, pp. 1-32.
30. A. D. Burrows, Struct. Bonding (Berlin) 2004, 108, 55-95.
31. P. Hubberstey, U. Suksangpanya, Hydrogen-bonded Supramolecular Chain and Sheet Formation by Coordinated Guanidine Derivatives, Springer, Berlin, 2004, pp. 33-83.
32. R. Vilar, Hydrogen-bonding Templated Assemblies, Springer, Berlin, 2004, pp. 85-137.
33. M. J. Hardie, Hydrogen-bonded Network Structures Constructed from Molecular Hosts, Springer, Berlin, 2004, pp. 139-174.
34. J. M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, Wiley-VCH, Weinheim, 1995.
35. I. Haiduc, F. T. Edelmann, Supramolecular Organometallic Chemistry, Wiley-VCH, Weinheim, 1999.
36. J. W. Steed, J. L. Atwood, Supramolecular Chemistry, Wiley, New York, 2000.
37. G. R. Desiraju, The Crystal as a Supramolecular Entity. Perspectives in Supramolecular Chemistry, Wiley, Chichester (UK), 1996.
38. A. G. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer, Berlin, 1991.
39. D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1405.
40. L. J. Prins, D. N. Reinhoudt, P. Timmerman, Angew. Chem. 2001, 113, 2446-2492;
41. Angew. Chem. Int. Ed. 2001, 40, 2382-2426.
42. L. Brammer, Dalton Trans. 2003, 3145-3157.
43. C. B. Aakeroy, K. R. Seddon, Chem. Soc. Rev. 1993, 22, 397-407.
44. D. Braga, F. Grepioni, Acc. Chem. Res. 2000, 33, 601-608.
45. A. M. Beatty, CrystEngComm 2001, 3, 243-255.
46. K. Biradha, CrystEngComm 2003, 5, 374-384.
47. H. W. Roesky, M. Andruh, Coord. Chem. Rev. 2003, 236, 91-119.
48. A. M. Beatty, Coord. Chem. Rev. 2003, 246, 131-143.
49. D. Braga, L. Maini, G. de Sanctis, K. Rubini, F. Grepioni, M. R. Chierotti, R. Gobetto, Chem. Eur. J. 2003, 9, 5538-5548.
50. G. R. Goward, I. Schnell, S. P. Brown, H. W. Spiess, H. D. Kim, H. Ishida, Magn. Reson. Chem. 2001, 39, S5-S17.
51. Z. T. Gu, R. Zambrano, A. McDermott, J. Am. Chem. Soc. 1994, 116, 6368-6372.
52. G. C. Levy, R. L. Lichter, Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy, Wiley, New York, 1979.
53. P. Lorente, I. G. Shenderovich, N. S. Golubev, G. S. Denisov, G. Buntkowsky, H. H. Limbach, Magn. Reson. Chem. 2001, 39, S18-829.
54. P. A. Frey, Magn. Reson. Chem. 2001, 39, S190-S198.
55. U. Sternberg, E. Brunner, J. Magn. Reson. Ser. A 1994, 108, 142-150.
56. R. Gobetto, C. Nervi, E. Valfrè, M. R. Chierotti, D. Braga, L. Maini, F. Grepioni, R. K. Harris, P. Y. Ghi, Chem. Mater. 2005, 17, 1457-1466.
57. J. C. Williams, A. E. McDermott, J. Phys. Chem. 1993, 97, 12393-12398.
58. L. Zheng, K. W. Fishbein, R. G. Griffin, J. Herzfeld, J. Am. Chem. Soc. 1993, 115, 6254-6261.
59. A. McDermott, C. F. Ridenour, Encyclopedia of NMR (Eds.: D.M. Grant, R. K. Harris), Wiley, Chichester, 1996, pp. 3820-3825.
60. A. S. Mildvan, T. K. Harris, C. Abeygunawardana, Methods Enzymol. 1999, 219-245.
61. D. Braga, L. Maini, Chem. Commun. 2004, 976-977.
62. D. Braga, K. Rubini, L. Maini, CrystEngComm 2004, 6, 236-238.
63. J. Herzfeld, A. E. Berger, J. Chem. Phys. 1980, 73, 6021-6030.
64. M. M. Maricq, J. S. Waugh, J. Chem. Phys. 1979, 70, 3300.
65. N. Someswara Rao, G. Babu Rao, B. N. Murthy, M. Maria Das, T. Prabhakar, M. Lalitha, Spectrochim. Acta Part A 2002, 58, 2737-2757.
66. R. K. Harris, A. C. Olivieri, Prog. Nucl. Magn. Reson. Spectrosc. 1992, 24, 435-456.
67. F. Filiaux, N. Leygue, J. Tomkinson, A. Cousson, W. Paulus, Chem. Phys. 1999, 244, 387-403.
68. C. R. Sun, Z. M. Jin, Acta Crystallogr. Sect. C 2002, 58, O600-O601.
69. K. F. Bowes, G. Ferguson, A. J. Lough, C. Glidewell, Acta Crystallogr. Sect. B 2003, 59, 100-117.
70. T. Nakai, C. A. McDowell, Chem. Phys. Lett. 1994, 227, 639-644.
71. R. Kubo, K. Tomita, J. Phys. Soc. Jpn. 1954, 9, 888-919.
72. U. Sternberg, E. Brunner, J. Magn. Reson. Ser, A 1994, 108, 142-150.
73. A. Gavezzotti, M. Simonetta, Acta Crystallogr. Sect. A 1976, 32, 997-1001.
74. G. M. Sheldrick, SHELXL97, Program for Crystal Structure Determination, University of Göttingen (Germany), 1997.
75. E. Keller, SCHAKAL99, Graphical Representation of Molecular Models, University of Freiburg (Germany), 1999.
76. PowderCell, programmed by W. Kraus, G. Nolze, BAM, Berlin (Germany), subgroups were derived by Ulrich Müller (GH Kassel).
77. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
78. Gaussian 98 (Revision A.9), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Forestman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzales, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1998.