Pyridine mediated supramolecular assemblies of 3,5-dinitro substituted benzoic acid, benzamide and benzonitrile

Tetrahedron

Volumn 61, Issue 45, 2005, Pages 10793-10800

  Arora, Kapildev K ^a   PrakashaReddy, Jayarama ^a   Pedireddi, Venkateswara Rao ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

3,5 Dinitrobenzamide; 3,5 Dinitrobenzoic acid; 3,5 Dinitrobenzonitrile; Channel structures; Host guest complexes; Layered structures; Molecular recognition; Pyridine

Indexed keywords

3,5 DINITROBENZOIC ACID; 3,5 DINITROBENZONITRILE; BENZAMIDE DERIVATIVE; BENZENE DERIVATIVE; BENZOIC ACID DERIVATIVE; BENZONITRILE; NITRO DERIVATIVE; NITROMIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; MOLECULAR BIOLOGY; MOLECULE; PRIORITY JOURNAL; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 26244434888     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.08.080     Document Type: Article

References (63)

1. C. Reichardt Solvent effects in organic chemistry 1979 Verlag Chemie Weinheim, New York
2. G.M. Whitesides, E.E. Simanek, J.P. Mathias, C.T. Seto, D.N. Chin, M. Mammen, and D.M. Gorden Acc. Chem. Res. 28 1995 37 44
3. V. Ramamurthy, and K. Venkatesan Chem. Rev. 87 1987 433 481
4. J.W. Mullin Crystallization 3rd ed. 1993 Butterworth-Heinemann London
5. N. Rodriguez-Hornedo, and D. Murphy J. Pharm. Sci. 88 1999 651 660
6. S.L. Morrissette, O. lmarsson, M.L. Peterson, J.F. Remenar, M.J. Read, A.V. Lemmo, S. Ellis, M.J. Cima, and C.R. Gardner Adv. Drug Deliv. Rev. 56 2004 275 300
7. J. Bernstein Polymorphism in molecular crystals 2002 Oxford University Press New York
8. J.D. Dunitz, and J. Bernstein Acc. Chem. Res. 28 1995 193 200
9. R.J. Davey Chem. Commun. 2003 1463 1467
10. J.A. McMahon, M.J. Zaworotko, and J.F. Remenar Chem. Commun. 2004 278 279
11. C.B. Aakeroy, M. Nieuwenhuyzen, and S.L. Price J. Am. Chem. Soc. 120 1998 8986 8993
12. V.R. Pedireddi CrystEngComm 15 2001 1 3
13. T. Beyer, G.M. Day, and S.L. Price J. Am. Chem. Soc. 123 2001 5086 5094
14. S.H. Dale, M.R.J. Elsegood, and C. Redshaw CrystEngComm 5 2003 368 373
15. T. Hosokawa, S. Datta, A.R. Sheth, N.R. Brooks, V.G. Young Jr., and D.J.W. Grant Cryst. Growth Des. 4 2004 1195 1201
16. V. Ischenko, U. Englert, and M. Jansen Chem. Eur. J. 11 2005 1375 1383
17. S. Mirza, I. Miroshnyk, J. Heinamaki, L. Christiansen, M. Karjalainen, and J. Yliruusi Pharm. Sci. 5 2003 1 9
18. C.-H. Gu, V. Young Jr., and D.J.W. Grant J. Pharma. Sci. 90 2001 1878 1890
19. S. Teychene, J.M. Autret, and B. Biscans Cryst. Growth Des. 4 2004 971 977
20. S. Veesler, N. Ferte, M.-S. Costes, M. Czjzek, and J.-P. Astier Cryst. Growth Des. 4 2004 1137 1141
21. S. Khoshkhoo, and J. Anwar J. Phys. D: Appl. Phys. 26 1993 B90 B93
22. P.T. Cardew, and R.J. Davey Proc. Roy. Soc. London. A 398 1982 415 428
23. N. Blagden, R.J. Davey, H.F. Lieberman, L. Williams, R. Payne, R. Roberts, R. Rowe, and R. Docherty J. Chem. Soc. Faraday Trans. 1998
24. M.R. Caira, K.A. Alkhamis, and R.M. Obaidat J. Pharma. Sci. 93 2004 601 611
25. V.R. Pedireddi, S. Chatterjee, A. Ranganathan, and C.N.R. Rao J. Am. Chem. Soc. 119 1997 10867 10868
26. S.H. Dale, and M.R.J. Elsegood Acta Crystallogr., Sect. E 59 2003 o1205 o1207
27. S.H. Dale, and M.R.J. Elsegood Acta Crystallogr., Sect. E 59 2003 o1087 o1088
28. S.H. Dale, and M.R.J. Elsegood Acta Crystallogr., Sect. C 60 2004 o444 o448
29. Z.M. Jin, Y.J. Pan, L. Shen, M.C. Li, and M.L. Hu Acta Crystallogr., Sect. C 59 2003 o205 o206
30. F. Takusagawa, K. Hirotsu, and A. Shimada Bull. Chem. Soc. Jpn. 44 1971 1274
31. A. Nangia, and G.R. Desiraju Chem. Commun. 1999 605 606
32. V.R. Pedireddi, and D. Belhekar Tetrahedron 58 2002 2937 2941
33. V.R. Pedireddi, and J. PrakashaReddy Tetrahedron Lett. 43 2002 4927 4930
34. V.R. Pedireddi, A. Ranganathan, and S. Chatterjee Tetrahedron Lett. 39 1998 9831 9834
35. V.R. Pedireddi, W. Jones, A.P. Chorlton, and R. Docherty Tetrahedron Lett. 39 1998 5409 5412
36. A. Ranganathan, and V.R. Pedireddi Tetrahedron Lett. 39 1998 1803 1806
37. V.R. Pedireddi, W. Jones, A.P. Chorlton, and R. Docherty Chem. Commun. 1996 987 988
38. V.R. Pedireddi, W. Jones, A.P. Chorlton, and R. Docherty Chem. Commun. 1996 997 998
39. J. PrakashaReddy, and V.R. Pedireddi Tetrahedron 60 2004 8817 8827
40. J. PrakashaReddy, and V.R. Pedireddi Tetrahedron Lett. 60 2004 6679 6681
41. V.R. Pedireddi, J. PrakashaReddy, and K.K. Arora Tetrahedron Lett. 44 2003 4857 4860
42. K.K. Arora, and V.R. Pedireddi Tetrahedron 60 2004 919 925
43. P. Prince, F.R. Fronczek, and R.D. Gandour Acta Crystallogr., Sect. C 47 1991 895 898
44. K. Sakai, R. Sakurai, and N. Hirayama Tetrahedron: Asymmetry 15 2004 1073 1076
45. K. Sakai, R. Sakurai, H. Nohira, R. Tanaka, and N. Hirayama Tetrahedron: Asymmetry 15 2005 3495 3500
46. K. Sakai, R. Sakurai, A. Yuzawa, and N. Hirayama Tetrahedron: Asymmetry 14 2003 3713 3718
47. F.H. Allen, J.E. Davies, J.J. Galloy, O. Johnson, O. Kennard, C.F. Macrae, and D.G. Watson J. Chem. Inf. Comput. Sci. 31 1991 204
48. We excluded organometallic compounds as pyridine take part as a ligand rather than as a solvate in the majority of their crystal structures.
49. P. Kilian, A.M.Z. Slawin, and J.D. Woollins Eur. J. Inorg. Chem. 1999 2327
50. D. Freeman, F. Frolow, E. Kapinus, D. Lavie, G. Lavie, D. Meruelo, and Y. Mazur Chem. Commun. 1994 891
51. P.C. Minshall, and G.M. Sheldrick Acta Crystallogr., Sect. B 34 1978 1378
52. Z. Olejnik, T. Lis, E. Grech, and J. Nowicka-Scheibe Pol. J. Chem. 72 1998 1255
53. M.K. Krepps, S. Parkin, and D.A. Atwood Cryst. Growth Des. 1 2001 291
54. K. Agbaria, S.E. Biali, V. Bohmer, J. Brenn, S. Cohen, M. Frings, F. Grynszpan, J.M.B. Harrowfield, A.N. Sobolev, and I. Thondorf J. Org. Chem. 66 2001 2900
55. D. Wiechert, and D. Mootz Angew. Chem., Int. Ed. 38 1999 1974 1976
56. D. Boenigk, and D. Mootz J. Am. Chem. Soc. 110 1988 2135 2139
57. D. Wiechert, D. Mootz, R. Franz, and G. Siegemund Chem. Eur. J. 4 1998 1043 1047
58. D. Boenigk, and D. Mootz Z. Kristallogr. 170 1985 16
59. Although the solvents of HPLC grade were used, since the crystallization was carried out at ambient conditions, the water in the crystal lattice of 1b could be attributed to the moisture in the atmosphere.
60. Siemens, SMART System; Siemens Analytical X-ray Instruments Inc: Madison, WI, USA, 1995.
61. Sheldrick, G. M. SADABS: Software for empirical absorption corrections; University of Gottingen: Gottingen, Germany, 2000.
62. Sheldrick, G. M. SHELXTL-PLUS: Program for crystal structure solution and refinements; University of Gottingen: Gottingen, Germany, 1997.
63. Spek, A. L. PLATON: Molecular geometry program; University of Utrecht, The Netherlands, 1995.