Balancing intermolecular hydrogen-bond interactions for the directed assembly of binary 1 : 1 co-crystals

New Journal of Chemistry

Volumn 30, Issue 10, 2006, Pages 1452-1460

  Aakeröy, Christer B ^a   Schultheiss, Nate ^a   Desper, John ^a   Moore, Curtis ^b  

^a KANSAS STATE UNIVERSITY   (United States)

^b WICHITA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPYRIDINE; CARBOXYLIC ACID; PYRIDINE;

BINDING SITE; CONFERENCE PAPER; CRYSTAL; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; STOICHIOMETRY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 33749506869     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/b608267j     Document Type: Conference Paper

References (49)

1. C. B. Aakeröy D. J. Salmon CrystEngComm 2005 7 439
2. J. W. Steed and J. L. Atwood, Supramolecular Chemistry, John Wiley and Sons Ltd, Chichester, 2000
3. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995
4. G. R. Desiraju, Crystal Engineering The Design of Organic Solids, Elsevier Science Publishers B.V., Amsterdam, 1989
5. M. Fujita M. Tominaga A. Hori B. Therrien Acc. Chem. Res. 2005 38 369
6. D. Fiedler D. H. Leung R. G. Bergman K. N. Raymond Acc. Chem. Res. 2005 38 349
7. M. W. Hosseini Acc. Chem. Res. 2005 38 313
8. M. Eddaoudi D. B. Moler H. Li B. Chen T. M. Reineke M. O'Keeffe O. M. Yaghi Acc. Chem. Res. 2001 34 319
9. L. MacGillivray CrystEngComm 2004 6 77
10. J.-M. Lehn Science 2002 295 2400
11. G. R. Desiraju Acc. Chem. Res. 2002 35 565
12. B. Moulton M. J. Zaworotko Chem. Rev. 2001 101 1629
13. G. R. Desiraju Angew. Chem., Int. Ed. Engl. 1995 34 2311
14. P. Metrangolo H. Neukirch T. Pilati G. Resnati Acc. Chem. Res. 2005 38 386
15. P. Metrangolo T. Pilati G. Resnati A. Stevenazzi Chem. Commun. 2004 1492
16. A. De Santis A. Forni R. Liantonio P. Metrangolo T. Pilati G. Resnati Chem.-Eur. J. 2003 9 3974
17. R. B. Walsh C. W. Padgett P. Metrangolo G. Resnati T. W. Hanks W. T. Pennington Cryst. Growth Des. 2001 1 165
18. N. Motohiro CrystEngComm 2004 6 130
19. S. Varaghese V. R. Pedireddi Chem.-Eur. J. 2006 12 1597
20. T. R. Shattock P. Vishweshwar Z. Wang M. J. Zaworotko Cryst. Growth Des. 2005 5 2046
21. C. B. Aakeröy J. Desper J. F. Urbina CrystEngComm 2005 7 193
22. D. Braga F. Grepioni Chem. Commun. 2005 3635
23. B. K. Saha A. Nangia M. Jaskolski CrystEngComm 2005 7 355
24. S. Basavoju A. Nangia Cryst. Growth Des. 2005 5 1683
25. C. B. Aakeröy A. M. Beatty B. A. Helfrich J. Am. Chem. Soc. 2002 124 14425
26. M. C. Etter Acc. Chem. Res. 1990 23 120
27. M. C. Etter J. Phys. Chem. 1991 95 4601
28. R. Langner C. J. Zundel J. Chem. Soc., Faraday Trans. 1995 91 3831
29. C. A. Hunter Angew. Chem., Int. Ed. 2004 43 5310
30. M. Henry M. W. Hosseini New J. Chem. 2004 28 897
31. Dissociation constants of organic bases in aqueous solutions, ed. D. D. Perrin, International Union of Pure and Applied Chemistry, Butterworths, London, 1965
32. Molecular structures were constructed using Spartan '04 (Wavefunction, Inc. Irvine, CA), and their geometries were optimized using AM1, with the maxima and minima in the electrostatic potential surface (0.002 e/au isosurface) determined using a positive point charge in vacuum as a probe
33. S. Valiyaveettil V. Enkelmann K. Mullen J. Chem. Soc., Chem. Commun. 1994 2097
34. Cambridge Structural Database ConQuest version 1.8
35. C. B. Aakeröy N. Schultheiss J. Desper Inorg. Chem. 2005 44 4983
36. SMART v5.060, © 1997-1999, Bruker Analytical X-ray Systems, Madison, WI
37. SAINT v6.02, © 1997-1999, Bruker Analytical X-ray Systems, Madison, WI
38. SHELXTL v5.10, © 1997, Bruker Analytical X-ray Systems, Madison, WI
39. The relatively high R-value for this structure was due to thin and poorly diffracting crystals
40. N. Shan A. D. Bond W. Jones New J. Chem. 2003 2 365
41. K. K. Arora V. R. Pedireddi J. Org. Chem. 2003 67 556
42. T. Sugiyama J. Meng T. Matsuura J. Mol. Struct. 2002 611 53
43. N. Shan E. Batchelor W. Jones Tetrahedron Lett. 2002 43 8721
44. B. R. Bhogala A. Nangia Cryst. Growth Des. 2002 2 325
45. M. J. Zaworotko Chem. Commun. 2001 1
46. K. Chinnakali H.-K. Fun S. Goswami A. K. Mahapatra G. D. Nigam Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1999 C55 399
47. S. Goswami A. K. Mahapatra K. Ghosh G. D. Nigam K. Chinnakali H.-K. Fun Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1999 C55 87
48. D. E. Lynch G. Smith K. A. Byriel C. H. L. Kennard Aust. J. Chem. 1998 51 403
49. G. Smith J. M. Gentner D. E. Lynch K. A. Byriel C. H. L. Kennard Aust. J. Chem. 1995 48 1151