The novel hydrogen bonding motifs and supramolecular patterns in 2,4-diaminopyrimidine-nitrobenzoate complexes

Tetrahedron

Volumn 61, Issue 30, 2005, Pages 7201-7210

  Stanley, N ^a   Muthiah, P T ^a   Geib, S J ^b   Luger, P ^c   Weber, M ^c   Messerschmidt, M ^c  

^a BHARATHIDASAN UNIVERSITY   (India)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Aminopyrimidine carboxylate interactions; Crystal engineering; Non covalent interactions; Self organization; Supramolecular chemistry

Indexed keywords

2,4 DIAMINOPYRIMIDINE DERIVATIVE; BENZOIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; NITROBENZOIC ACID DERIVATIVE; PYRIMETHAMINE; PYRIMETHAMINE 2 NITROBENZOATE; PYRIMETHAMINE 3 NITROBENZOATE; PYRIMETHAMINE 4 NITROBENZOATE; TRIMETHOPRIM; TRIMETHOPRIM 3 NITROBENZOATE; TRIMETHOPRIM 4 NITROBENZOATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HYDROGEN BOND; PRIORITY JOURNAL; PROTON TRANSPORT; SUPRAMOLECULAR CHEMISTRY;

EID: 20444508197     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.033     Document Type: Article

References (51)

1. J.-M. Lehn Supramolecular Chemistry 1995 VCH Weinheim
2. G.R. Desiraju Crystal Engineering: The Design of Organic Solids 1989 Elsevier Amsterdam
3. B. Moulton, and M.J. Zaworotko Chem. Rev. 101 2001 1629 1658
4. G.R. Desiraju Nature 412 2001 397 400
5. G.R. Desiraju Curr. Sci. 81 2001 1038 1042
6. B. Rodrǐguez-Spong, C.P. Price, A. Jayasankar, A.J. Matzger, and N. Rodrǐguez-Hornedo Adv. Drug Deliv. Rev. 56 2004 241 274
7. G.R. Desiraju J. Mol. Struct. 656 2004 5 15
8. L.J. Prins, D.N. Reinhoudt, and P. Timmerman Angew. Chem., Int. Ed. 40 2001 2382 2426
9. G.A. Jeffrey Introduction to Hydrogen Bonding 1997 Oxford University Press New York
10. C.B. Aakeröy Acta Crystallogr., Sect. B 53 1997 569 586
11. G.A. Jeffrey, and W. Saenger Hydrogen Bonding in Biological Structures 1991 Springer Berlin
12. F.H. Beijer, R.P. Sijbesma, H. Kooijman, A.L. Spek, and E.W. Meijer J. Am. Chem. Soc. 120 1998 6761 6769
13. S. Fernandez-Lopez, H.-S. Kim, E.C. Choi, M. Delgado, J.R. Granja, A. Khasanov, K. Kraehenbuehl, G. Long, D.A. Weinberger, K.M. Wilcoxen, and M.R. Ghadiri Nature 412 2001 452 455
14. B.L. Vallee, and D.S. Auld Acc. Chem. Res. 26 1993 543 551
15. L.F. Kuyper C.E. Bugg S.E. Ealick Crystallographic and Modelling Methods in Molecular Design 1990 Springer New York 56
16. M.C. Etter, and D.A. Adsmond J. Chem. Soc., Chem. Commun. 1990 589 591
17. M.C. Etter J. Phys. Chem. 95 1991 4601 4610
18. S. Goswami, A.K. Mahapatra, G.D. Nigam, K. Chinnakali, H.-K. Fun, and I.A. Razak Acta Crystallogr., Sect. C 55 1999 583 585
19. S. Goswami, A.K. Mahapatra, K. Ghosh, G.D. Nigam, K. Chinnakali, and H.-K. Fun Acta Crystallogr. 155 1999 87 89
20. N. Shan, A.D. Bond, and W. Jones Tetrahedron Lett. 43 2002 3101 3104
21. V.R. Pedireddi, S. Chatterjee, A. Renganathan, and C.N.R. Rao Tetrahedron 54 1998 9457 9474
22. G.H. Hitchings, and J.J. Burchall F. Nord Advances in Enzymology Vol. 27 1965 Interscience New York 417
23. S. Murugesan, and P.T. Muthiah Acta Crystallogr., Sect. C 53 1997 763 764
24. Murugesan, S.; Muthiah, P. T. Academic Discussion Meeting on Frontiers in Structural Chemistry, I.I.T., Chennai, India, 1996; Abstract No. 3.4.
25. P. Prabakaran, J.J. Robert, P.T. Muthiah, G. Bocelli, and L. Righi Acta Crystallogr., Sect. C 57 2001 459 461
26. B. Umadevi, P. Prabakaran, and P.T. Muthiah Acta Crystallogr., Sect. C 58 2002 510 512
27. P.T. Muthiah, B. Umadevi, N. Stanley, G. Bocelli, and A. Cantoni Acta Crystallogr., Sect. E 58 2002 o59 o61
28. P.T. Muthiah, B. Umadevi, N. Stanley, N. Shui, and D.S. Eggleston Acta Crystallogr., Sect. C 57 2001 o1179 o1182
29. J.J. Robert, S.B. Raj, and P.T. Muthiah Acta Crystallogr., Sect. E 59 2001 o1206 o1208
30. P. Panneerselvam, N. Stanley, and P.T. Muthiah Acta Crystallogr., Sect. E 58 2002 o180 o182
31. S.B. Raj, V. Sethuraman, S. Francis, M. Hemamalini, P.T. Muthiah, G. Bocelli, A. Cantoni, U. Rychlewska, and B. Warzajtis CrystEngComm. 5 2003 70 76
32. R.F. Bryan, and C.R. Haltiwanger Acta Crystallogr., Sect. C 43 1987 2412 2415
33. G. Giuseppetti, C. Tadini, G.P. Bettinetti, F. Giordano, and A.-L. Manna Acta Crystallogr., Sect. C 44 1988 856 860
34. S. Francis, P.T. Muthiah, G. Bocelli, and L. Righi Acta Crystallogr., Sect. E 58 2002 o717 o719
35. M. Hemamalini, P.T. Muthiah, G. Bocelli, and A. Cantoni Acta Crystallogr., Sect. E 59 2003 o14 o17
36. S.B. Raj, P.T. Muthiah, U. Rychlewska, and B. Warzajtis CrystEngComm 5 2003 48 53
37. N. Stanley, V. Sethuraman, P.T. Muthiah, P. Luger, and M. Weber Cryst. Growth Des. 2 2002 631 635
38. V. Sethuraman, N. Stanley, P.T. Muthiah, W.S. Sheldrick, M. Winter, P. Luger, and M. Weber Cryst. Growth Des. 3 2003 823 828
39. T.F. Koetzle, and G.J.B. Williams J. Am. Chem. Soc. 98 1976 2074 2078
40. V. Sethuraman, and P.T. Muthiah Acta Crystallogr., Sect. E 58 2002 o817 o818
41. G.H. Hitchings, L.F. Kuyper, and D.P. Baccananari M. Sandler H.J. Smith Design of Enzyme Inhibitors as Drugs 1988 Oxford University Press New York
42. C.E. Sansom, C.H. Schwalbe, P.A. Lambert, R.J. Griffn, and M.F.G. Stevens Biochem. Biophys. Acta 995 1989 21 27
43. F.H. Allen, P.R. Raithby, G.P. Shields, and R. Taylor Chem. Commun. 1998 1043 1044
44. M.C. Etter Acc. Chem. Res. 23 1990 120 126
45. J. Bernstein, R.E. Davis, L. Shimoni, and N.-L. Chang Angew. Chem., Int. Ed. Engl. 34 1995 1555 1573
46. S. Aitipamula, P.K. Thallapally, R. Thaimattam, M. Jaskǒlski, and G.R. Desiraju Org. Lett. 4 2002 92 924
47. P.K. Thallapally, and A. Nangia CrystEngComm 3 2001 114 119
48. Sheldrick, G. M. SHELXS97 and SHELXL97; University of Göttingern, Germany, 1997.
49. L.J. Farrugia J. Appl. Crystallogr. 30 1997 565
50. Spek, A. L. PLATON97; Utrecht University: The Netherlands, 1997.
51. B.S. Raj, N. Stanley, P.T. Muthiah, G. Bocelli, R. Olla, and A. Cantoni Cryst. Growth Des. 3 2003 567 571