1H NMR and crystallographic evidence for tolerance of bulky electron withdrawing methanesulfonyl group on robustness of the U-motif in pyrazolo[3,4-d]pyrimidine core based 'Leonard linker' compounds and formation of plus (+) motif

Journal of Molecular Structure

Volumn 827, Issue 1-3, 2007, Pages 88-94

  Avasthi, Kamlakar ^a   Farooq, Sheikh M ^a   Aswal, Sangeeta ^a   Raghunandan, Resmi ^a   Maulik, Prakas R ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Arene interactions; Chain motif and plus motif; U motif; X ray crystallography

Indexed keywords

MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; OLEFINS; ROBUSTNESS (CONTROL SYSTEMS); X RAY CRYSTALLOGRAPHY;

ARENE INTERACTIONS; CHAIN MOTIF; PLUS MOTIF; U-MOTIF;

ELECTRONS;

EID: 33846525423     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2006.05.022     Document Type: Article

References (64)

1. Piacenza M., and Grimme S. Chem. Phys. Chem. 6 (2005) 1554
2. Sinnokrot M.O., and Sherrill C.D. J. Phys. Chem. A 108 (2004) 10200
3. Oh M., Carpenter G.B., and Sweigart D.A. Acc. Chem. Res. 37 (2004) 1
4. Tsuzuki S., Honda K., Uchimaru T., Mikami M., and Tanabe K. J. Am. Chem. Soc. 124 (2002) 104
5. Hunter C.A., Lawson K.R., Perkins J., and Urch C.J. J. Chem. Soc., Perkin Trans. 2 (2001) 651
6. Cantrill S.J., Pease A.R., and Stoddart J.F. J. Chem. Soc. Dalton Trans. (2000) 3715
7. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford University Press, Oxford
8. Dahl T. Acta Chem. Scand. 48 (1994) 95
9. Burley S.K., and Petsko G.A. Science 229 (1985) 23
10. Waters M.L. Curr. Opin. Chem. Biol. 6 (2002) 727
11. Hunter C.A. J. Chem. Soc. Rev. (1994) 101
12. Hobza P., and Sponer J. Chem. Rev. 99 (1999) 3247
13. Hunter C.A. J. Mol. Biol. 230 (1993) 1025
14. Kool E.T., Morales J.C., and Guckian K.M. Angew. Chem., Int. Ed. Engl. 39 (2000) 990
15. Desiraju G.R. Angew. Chem., Int. Ed. Engl. 34 (1995) 2311
16. Desiraju G.R. Crystal Engineering: The Design of Organic Solids (1989), Elsevier, New York
17. Tanaka T., Tasaki T., and Aoyama Y. J. Am. Chem. Soc. 124 (2004) 12453
18. Hill D.J., Mio M.J., Prince R.B., Hughes T.S., and Moore J.S. Chem. Rev. 101 (2001) 3893
19. Lerman L.S. Proc. Natl. Acad. Sci. USA 49 (1963) 94
20. Klarner F.G., and Kahlert B. Acc. Chem. Res. 36 (2003) 919 and references therein
21. Meyer E.A., Castellano R.K., and Diederich F. Angew. Chem., Int. Ed. Engl. 42 (2003) 1210 and references therein
22. Browne D.T., Eisinger J., and Leonard N.J. J. Am. Chem. Soc. 90 (1968) 7302
23. Leonard N.J. Acc. Chem. Res. 12 (1979) 423 and references therein
24. Bunic G., and Voet D. Acta Crystallogr. B38 (1982) 575
25. Ishida T., Shibata M., Fuiji, and Inoue M. Biochemistry 22 (1983) 3571
26. Newcomb L.F., and Gellman S.H. J. Am. Chem. Soc. 116 (1994) 4993
27. Itahara T. Heterocycles 57 (2002) 1247
28. Itahara T. J. Chem. Soc., Perkin Trans. 2 (1996) 2695
29. Bolte J., Colette D., Lhomme J., Fournie-Zaluski M.C., and Roques B.P. Biochemistry 18 (1979) 4928
30. Pang Y.P., Miller J.L., and Kollman P.A. J. Am. Chem. Soc. 121 (1999) 1717
31. Hunter C.A., and Sanders J.K.M. J. Am. Chem. Soc. 112 (1990) 5525
32. Mishra B.K., and Sathyamurthy N. J. Phys. Chem. A. 109 (2005) 6
33. Nishio M. Cryst. Eng. Commun. 6 (2004) 130
34. Cubberley M.S., and Iverson B.L. J. Am. Chem. Soc 123 (2001) 7560
35. Martin C.B., Mulla H.R., Willis P.G., and Cammers-Goodwin P.A. J. Org. Chem. 64 (1999) 7802
36. Cozzi F., and Siegel J.S. Pure Appl. Chem. 67 (1995) 683
37. Newcomb L.F., Haque T.F., and Gellman S.H. J. Am. Chem. Soc. 117 (1995) 6509
38. Hunter C.A. Angew. Chem. Int. Ed. Engl. 35 (1993) 1584
39. Steed J.W., and Atwood J.L. Supramolecular Chemistry (2000), Wiley, UK
40. Lehn J.M. Supramolecular Chemistry: Concepts and Perspectives (1995), VCH, New York
41. Rashkin M.J., and Waters M.L. J. Am. Chem. Soc. 124 (2002) 1860 and references therein
42. Sinnokrot M.O., and Sherrill C.D. J. Am. Chem. Soc. 126 (2004) 7690 and references therein
43. Avasthi K., Chandra T., and Bhakuni D.S. Indian J. Chem. 34B (1995) 944
44. Biswas G., Chandra T., Avasthi K., and Maulik P.R. Acta Crystallogr. C51 (1995) 2453
45. Avasthi K., Rawat D.S., Maulik P.R., Sarkhel S., Broder C., and Howard J.A.K. Tetrahedron Lett. 42 (2001) 7115
46. Avasthi K., Farooq S.M., Rawat D.S., Sharon A., and Maulik P.R. Acta Crystallogr. C59 (2003) o523
47. Avasthi K., Rawat D.S., Chandra T., and Bhakuni D.S. Indian J. Chem. 37B (1998) 754
48. 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
49. Avasthi K., Aswal S., and Maulik P.R. Acta Crystallogr. C57 (2001) 1324
50. Avasthi K., Tewari A., Rawat D.S., Sharon A., and Maulik P.R. Acta Crystallogr. C58 (2002) 494
51. Avasthi K., Aswal S., Kumar R., Yadav U., Rawat D.S., and Maulik P.R. J. Mol. Struct. 750 (2005) 179
52. Avasthi K., Farooq S.M., Raghunandan R., and Maulik P.R. J. Mol. Struct. 785 (2006) 106
53. Maulik P.R., Avasthi K., Sarkhel S., Chandra T., Rawat D.S., Logsdon B., and Jacobson R.A. Acta Crystallogr. C56 (2000) 1361
54. Avasthi K., Rawat D.S., Sarkhel S., and Maulik P.R. Acta Crystallogr. C58 (2002) o325
55. Avasthi K., Bhagat D., Bal C., Sharon A., Yadav U., and Maulik P.R. Acta Crystallogr. C59 (2003) o409
56. Programs: Siemens XSCANS Version 2.21. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA, 1996.
57. Bruker SHELXTL-NT Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA, 1997.
58. A.L. Speck, PLATON, Programme for Analysis of Crystal Data, University of Utrecht, Netherlands, 2005.
59. MERCURY, Version 1.4. Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, United Kingdom.
60. Janiak C. J. Chem. Soc. Dalton Trans. (2000) 3885 and references therein
61. Benoit D.M., Coumbarides G.S., Dingjan M., Eames J., Ghilagaber S., and Motevalli M. Cryst. Eng. Commun. 7 (2005) 454
62. Glidewell C., Harrison W.T.A., Low J.N., Sime J.G., and Wardell J.L. Acta Crystallogr. B57 (2001) 190
63. Wolf W.M. Acta Crystallogr. B57 (2001) 806
64. Wardell J.L., Low J.N., and Glidewell C. Acta Crystallogr. C56 (2000) 862