Hydrogen bonded binary molecular adducts derived from exobidentate N-donor ligand with dicarboxylic acids: Acid⋯imidazole hydrogen-bonding interactions in neutral and ionic heterosynthons

Journal of Molecular Structure

Volumn 985, Issue 2-3, 2011, Pages 361-370

  Kathalikkattil, Amal Cherian ^a   Damodaran, Subin ^a   Bisht, Kamal Kumar ^a   Suresh, Eringathodi ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Cocrystal; Hydrogen bond; Molecular adduct; Organic salt; pKa values; Supramolecular assembly

Indexed keywords

CO-CRYSTALS; MOLECULAR ADDUCT; ORGANIC SALT; PKA VALUES; SUPRAMOLECULAR ASSEMBLIES;

AZOBENZENE; BENZENE; CARBOXYLATION; CARBOXYLIC ACIDS; HYDROGEN; HYDROGEN BONDS; NAPHTHALENE; ORGANIC COMPOUNDS; PLANTS (BOTANY); SUPRAMOLECULAR CHEMISTRY;

COMPLEXATION;

EID: 78650679862     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2010.11.022     Document Type: Article

References (50)

1. J.A. Bis, O.L. McLaughlin, P. Vishweshwar, and M.J. Zaworotko Cryst. Growth Des. 6 2006 2648
2. M. Du, Z.H. Zhang, X.J. Zhao, and H. Cai Cryst. Growth Des. 4 2006 14
3. B. Sarma, L.S. Reddy, and A. Nangia Cryst. Growth Des. 8 2008 4546
4. N.S. Goroff, S.M. Curtis, J.A. Webb, F.W. Fowler, and J.W. Lauher Org. Lett. 7 2005 1891
5. L.Y. Park, D.G. Hamilton, E.A. McGehee, and K.A. McMenimen J. Am. Chem. Soc. 125 2003 10586
6. S. Mohamed, D.A. Tocher, M. Vickers, P.G. Karamertzanis, and S.L. Price Cryst. Growth Des. 9 2009 2881
7. W.W. Porter, S.C. Elie, and A.J. Matzger Cryst. Growth Des. 8 2008 14
8. G.R. Desiraju CrystEngComm 2003 466
9. D.J. Dunitz CrystEngComm 2003 506
10. A. Jayasankar, A. Somwangthanaroj, Z.J. Shao, and N.R. Hornedo Pharm. Res. 23 2006 2381
11. F.H. Allen, W.D.S. Motherwell, P.R. Raithby, G.P. Shields, and R. Taylor New J. Chem. 23 1999 25
12. J.M. Lehn Supramolecular Chemistry: Concepts and Perspectives 1995 VCH Weinheim
13. T. Sugiyama, J. Meng, and T. Matsuura J. Mol. Struct. 611 2002 53
14. C.B. Aakeröy, A.M. Beatty, and B.A. Helfrich J. Am. Chem. Soc. 124 2002 14425
15. G.R. Desiraju Angew. Chem., Int. Ed., Engl. 34 1995 2311
16. C.B. Aakeröy, and K.R. Seddon Chem. Soc. Rev. 22 1993 397
17. K.T. Holman, A.M. Pivovar, J.A. Swift, and M.D. Ward Acc. Chem. Res. 34 2001 107
18. C.B. Aakeröy, A.M. Beatty, and D.S. Leinen Cryst. Growth Des. 1 2001 47
19. K. Tanaka, K. Endo, and Y. Aoyama Chem. Lett. 1999 887
20. O. Almarsson, and M.J. Zaworotko Chem. Commun. 2004 1889
21. J. Xiao, M. Yang, J.W. Lauher, and F.W. Fowler Angew. Chem. Int. Ed. 39 2000 2132
22. J.M. Lehn, M. Mascal, A. DeCian, and J. Fischer J. Chem. Soc., Chem. Commun. 1990 479
23. S. Shan, E. Batchelor, and W. Jones Tetrahedron Lett 43 2002 8721
24. V.R. Pedireddi, S. Chatterjee, A. Ranganathan, and C.N.R. Rao J. Am. Chem. Soc. 119 1997 10867
25. C.B. Aakeröy, D.J. Salmon, M.M. Smith, and J. Desper Cryst. Growth Des. 6 2006 1033
26. B.F. Hoskins, R. Robson, and D.A. Slizys J. Am. Chem. Soc. 119 1997 2952
27. L. Carlucci, G. Ciani, and D.M. Proserpio Cryst. Growth Des. 5 2005 37
28. L. Carlucci, G. Ciani, D.M. Proserpio, and L. Spadacini CrystEngComm 6 2004 96
29. M.H. Zeng, B. Wang, X.Y. Wang, W.X. Zhang, X.M. Chen, and S. Gao Inorg.Chem. 45 2006 7069
30. B.F. Abrahams, F. Brendan, B.F. Hoskins, R. Robson, and D.A. Slizys CrystEngComm 4 2002 478
31. L.L. Wen, D.B. Dang, C.Y. Duan, Z.Y. Li, Z.F. Tian, and Q.J. Meng Inorg.Chem. 44 2005 7161
32. Z. Lu, L. Wen, Z. Ni, Y. Li, H. Zhu, and Q. Meng Cryst. Growth Des. 7 2007 268
33. D.R. Trivedi, A. Ballabh, and P. Dastidar CrystEngComm 5 2003 358
34. J. Overgaard, B. Schiøtt, F.K. Larsen, A.J. Schultz, J.C. MacDonald, and B.B. Iversen Angew Chem. Int. Ed. 38 1999 1239
35. C.B. Aakeröy, D.P. Hughes, and M. Nieuwenhuyzen J. Am. Chem. Soc. 118 1996 10134
36. F.A. Allen Acta Crystallogr., Sect. B 58 2002 380
37. C.B. Aakeröy, J. Desper, B. Leonard, and J.F. Urbina Cryst. Growth Des. 5 2005 865
38. Y.-L. Peng, and L.-H. Jia Acta Cryst E65 2009 o365
39. G.M. Sheldrick SAINT 5.1 ed. 1995 Siemens Industrial Automation Inc. Madison, WI
40. SADABS, Empirical Absorption Correction Program, University of Göttingen, Göttingen, Germany, 1997.
41. G.M. Sheldrick, SHELXTL Reference Manual: Version 5.1, Bruker AXS, Madison, WI, 1997.
42. G.M. Sheldrick, SHELXL-97: Program for Crystal Structure Refinement, University of Göttingen, Göttingen, Germany, 1997.
43. A.L. Spek J. Appl. Cryst. 36 2003 7
44. L.J. Farrugia J. Appl. Cryst. 30 1997 565
45. C.F. Macrae, P.R. Edgington, P. McCabe, E. Pidcock, G.P. Shields, R. Taylor, M. Towler, and J.V. Streek J. Appl. Cryst. 39 2006 453
46. B.F. Abrahams, B.F. Hoskins, R. Robson, and D.A. Slizys Acta Cryst. C54 1998 1666
47. pKa Values for the Acids and Base were obtained either from pKa Data Compiled by R. Williams, < http://research.chem.psu.edu/brpgroup/pKa- compilation.pdf >, from the Merck Index or by using Scifinder.
48. P.H. Stahl, and C.G. Wermuth Handbook of Pharmaceutical Salts: Properties, Selection, and Use International Union of Pure and Applied Chemistry 2002 VHCA, Wiley-VCH Weinheim, New York
49. S.L. Johnson, and K.A. Rumon J. Phys. Chem. 69 1965 74
50. B. Sarma, N.K. Nath, B.R. Bhogala, and A. Nangia Cryst. Growth Des. 9 2009 1546 (and references therein)