Design and synthesis of pyrazolo[3,4-d]pyrimidine and triazolo[4,5-d]pyrimidine based dissymmetrical 'Leonard linker' compounds: 1H NMR and crystallographic evidence for folded conformation due to arene interactions

Journal of Molecular Structure

Volumn 842, Issue 1-3, 2007, Pages 100-108

  Avasthi, Kamlakar ^a   Farooq, Sheikh M ^a   Bal, Chandralata ^a   Kumar, Rishi ^a   Tewari, Ashish K ^a   Maulik, Prakas R ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Arene interactions; Chain motif; S...arene interaction; U motif; X ray crystallography

Indexed keywords

CONFORMATIONS; MOLECULAR INTERACTIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

ARENE INTERACTIONS; CHAIN MOTIF; DISSYMMETRICAL COMPOUND;

ORGANIC COMPOUNDS;

EID: 34548312560     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2006.12.029     Document Type: Article

References (65)

1. Mignon P., Loverix S., and Geerlings P. Chem. Phys. Lett. 401 (2005) 40
2. Sinnokrot M.O., and Sherrill C.D. J. Am. Chem. Soc. 126 (2004) 7690
3. Tsuzuki S., Honda K., Uchimaru T., Mikami M., and Tanabe K. J. Am. Chem. Soc. 124 (2002) 104
4. Hunter C.A., Lawson K.R., Perkins J., and Urch C.J. J. Chem. Soc. Perkin Trans. 2 (2001) 651
5. Janiak C. J. Chem. Soc., Dalton Trans. (2000) 3885
6. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford University Press, UK
7. Dahl T. Acta Chem. Scand. 48 (1994) 95
8. Burley S.K., and Petsko G.A. Science 229 (1985) 23
9. Hunter C.A. J. Chem. Soc. Rev. (1994) 101
10. Hobza P., and Sponer J. Chem. Rev. 99 (1999) 3247
11. Hunter C.A. J. Mol. Biol. 230 (1993) 1025 (and references therein)
12. Desiraju G.R. Angew. Chem. Int. Ed. Engl. 34 (1995) 2311
13. Desiraju G.R. Crystal Engineering: The Design of Organic Solids (1989), Elsevier, New York
14. Tanaka T., Tasaki T., and Aoyama Y. J. Am. Chem. Soc. 124 (2002) 12453
15. Hill D.J., Mio M.J., Prince R.B., Hughes T.S., and Moore J.S. Chem. Rev. 101 (2001) 3893
16. Klarner F.G., and Kahlert B. Acc. Chem. Res. 36 (2003) 919 (and references therein)
17. Harmata M. Acc. Chem. Res. 37 (2004) 862 (and references therein)
18. Meyer E.A., Castellano R.K., and Diederich F. Angew. Chem. Int. Ed. Engl. 42 (2003) 1210 (and references therein)
19. Browne D.T., Eisinger J., and Leonard N.J. J. Am. Chem. Soc. 90 (1968) 7302
20. Leonard N.J. Acc. Chem. Res. 12 (1979) 423 (and references therein)
21. Hunter C.A., and Sanders J.K.M. J. Am. Chem. Soc. 112 (1990) 5525
22. Sugiura H., Takahira Y., and Yamaguchi M. J. Org. Chem. 70 (2005) 5698
23. Nishio M. Cryst. Eng. Commun. 6 (2004) 130
24. Arvinda S., Shamala N., Das C., Sriranjini A., Karle I.L., and Balram P. J. Am. Chem. Soc. 125 (2003) 5308
25. Cozzi F., and Siegel J.S. Pure Appl. Chem. 67 (1995) 683
26. Newcomb L.F., F Haque T., and Gellman S.H. J. Am. Chem. Soc. 117 (1995) 6509
27. Hunter C.A. Angew. Chem. Int. Ed. Engl. 35 (1993) 1584
28. Steed J.W., and Atwood J.L. Supramolecular Chemistry (2000), John Wiley & Sons, U.K.
29. Lehn J.M. Supramolecular Chemistry: Concepts and Perspectives (1995), VCH, New York
30. Rashkin M.J., and Waters M.L. J. Am. Chem. Soc. 124 (2002) 1860 (and references therein)
31. Avasthi K., Chandra T., and Bhakuni D.S. Indian J. Chem. 34B (1995) 944
32. Biswas G., Chandra T., Avasthi K., and Maulik P.R. Acta Crystallogr. C51 (1995) 2453
33. Avasthi K., Rawat D.S., Maulik P.R., Sarkhel S., Broder C., and Howard J.A.K. Tetrahedron Lett. 42 (2001) 7115
34. Avasthi K., Farooq S.M., Rawat D.S., Sharon A., and Maulik P.R. Acta Crystallogr. C59 (2003) o523
35. Avasthi K., Rawat D.S., Chandra T., and Bhakuni D.S. Indian J. Chem. 37B (1998) 754
36. Maulik P.R., Avasthi K., Biswas G., Biswas S., Rawat D.S., Sarkhel S., Chandra T., and Bhakuni D.S. Acta Crystallogr. C54 (1998) 275
37. Avasthi K., Aswal S., and Maulik P.R. Acta Crystallogr. C57 (2001) 1324
38. Avasthi K., Tewari A., Rawat D.S., Sharon A., and Maulik P.R. Acta Crystallogr. C58 (2002) o494
39. Avasthi K., Aswal S., Kumar R., Yadav U., Rawat D.S., and Maulik P.R. J. Mol. Structure 750 (2005) 179
40. Avasthi K., Farooq S.M., Aswal S., Raghunandan R., and Maulik P.R. J. Mol. Structure 827 (2006) 88
41. Avasthi K., Farooq S.M., Raghunandan R., and Maulik P.R. J. Mol. Structure 785 (2006) 106
42. Maulik P.R., Avasthi K., Sarkhel S., Chandra T., Rawat D.S., Logsdon B., and Jacobson R.A. Acta Crystallogr. C56 (2000) 1361
43. Avasthi K., Rawat D.S., Sarkhel S., and Maulik P.R. Acta Crystallogr. C58 (2002) 325
44. Avasthi K., Bhagat D., Bal C., Sharon A., Yadav U., and Maulik P.R. Acta Crystallogr. C59 (2003) o409
45. Jennings W.B., Farrell B.M., and Malone J.M. Acc. Chem. Res. 34 (2001) 885 (and references therein)
46. Bunick G., and Voet D. Acta Crystallogr. B38 (1982) 575
47. Maulik P.R., Avasthi K., Sarkhel S., Sharon A., Rawat D.S., and Bal C. Acta Crystallogr. E57 (2001) o1163
48. Liu Q.Y., and Xu L. CrystEngComm. 7 (2005) 87
49. Asker E., and Masnovi J. Acta Crystallogr. E61 (2005) o2781
50. Akkurt M., Yidirim S.O., Kucukbay H., Sireci N., and Buyukgungor O. Acta Crystallogr. E62 (2006) o3184
51. Akkurt M., Yidirim S.O., Kucukbay H., Sireci N., and Buyukgungor O. Acta Crystallogr. E62 (2006) o3512
52. Arslan M., Asker E., Masnovi J., and Baker R.J. Acta Crystallogr. E62 (2006) o3650
53. Meng X.G., and Mei F.-S. Zhan-Ru Liao. Acta Cryst. E62 (2006) o4120
54. Brycki B., Kowalczyk I., Werner J., Borowwiak T., and Wolska I. J. Mol. Structure 791 (2006) 137
55. Raso A.G., Fiol J.J., Badenas F., Solans X., and Font-Bardia M. Polyhedron 18 (1999) 765
56. Pang Y.P., Miller J.L., and Kollman P.A. J. Am. Chem. Soc. 121 (1999) 1717
57. Dille K.L., and Chrisensen B.E. J. Am. Chem. Soc. 76 (1954) 5087
58. Seela F., Jawalekar A.M., and Munster I. Helv. Chim. Acta 88 (2005) 751
59. Siemens XSCANS Version 2.21. Siemens analytical X-ray Instruments Inc.Madison, Wisconsin,USA; 1996.
60. Bruker SHELXTL-NT. Version 5.10. Bruker AXS Inc., Madison,Wisconsin,USA;1997.
61. A.L. Spek, PLATON, programme for analysis of crystal data, University of Utrecht, Netherlands; 2005.
62. MERCURY, Version 1.4. Cambridge Crystallographic data centre, 12 Union Road, Cambridge CB2 1EZ, United Kingdom.
63. Pal D., and Chakrabarty P. J. Biomol. Struct. Dynam. 19 (2001) 115 (and references therein)
64. Steiner T. Angew. Chem. Int. Ed. 41 (2002) 48 (and references therein)
65. Mehta G., Gagliardini V., Schaefer C., and Gleiter R. Org. Lett. 6 (2004) 1617