Role of positional isomers on receptor-anion binding and evidence for resonance energy transfer

Tetrahedron

Volumn 63, Issue 48, 2007, Pages 12007-12014

  Jose, D Amilan ^a   Kumar, D Krishna ^a   Kar, Prasenjit ^a   Verma, Sandeep ^b   Ghosh, Amrita ^a   Ganguly, Bishwajit ^a   Ghosh, Hirendra N ^b   Das, Amitava ^a  

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

^b BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANION;

AB INITIO CALCULATION; ARTICLE; BINDING AFFINITY; ENERGY TRANSFER; FLAME PHOTOMETRY; ISOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON TRANSPORT; SPECTROSCOPY;

EID: 35348907848     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.008     Document Type: Article

References (62)

1. Ullman's Encyclopedia of Industrial Chemistry. 6th ed. (1998), Wiley-VCH, New York, NY, Germany
2. Krik K.L. Biochemistry of Halogens and Inorganic Halides (1991), Plenum, New York, NY p 59l
3. Rurack K., and Resch-Genger U. Chem. Soc. Rev. 31 (2002) 116-127
4. Tajc S.G., and Miller B.L. J. Am. Chem. Soc. 128 (2006) 2532-2533
5. For an overview on anion sensors please see following articles:
6. In: Bianchi E., Bowman-James K., and Garcia-Espana E. (Eds). Supramolecular Chemistry of Anions (1997), Wiley-VCH, New York, NY
7. Gale P.A. Amide and Urea Based Anion Receptors. Encyclopedia of Supramolecular Chemistry (2004), Marcel Dekker, New York, NY 31
8. Sukasai C., and Tuntulani T. Chem. Soc. Rev. 32 (2003) 192-202
9. Gale P.A. Acc. Chem. Res. 39 (2006) 465-475
10. Martinez-Manez R., and Sancenon F. Chem. Rev. 103 (2003) 4419-4476
11. De Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Hauxley A.J.M., McCoy C.P., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515-1566
12. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 486-516
13. Yoon J., Kim S.K., Singh J., and Kim K.S. Chem. Soc. Rev. 35 (2006) 355-360
14. Gunnlaugsson T., Glynn M., Tocci G.M., Kruger P.E., and Pfeffer F.M. Coord. Chem. Rev. 250 (2006) 3094-3117
15. Gunnlaugsson T., Davis A.P., Hussey G.M., Tierney J., and Glynn M. Org. Biomol. Chem. 2 (2004) 1856-1863
16. Pfeffer F.M., Seter M., Lewcenko N., and Barnett N.W. Tetrahedron Lett. 47 (2006) 5241-5244
17. Lee J.Y., Cho E.J., Mukamel S., and Nam K.C. J. Org. Chem. 69 (2004) 943-950
18. Xu G., and Tarr M.A. Chem. Commun. (2004) 1050-1052
19. Wu C.-Y., Chen M.-S., Lin C.-A., Lin S.-C., and Sun S.-S. Chem.-Eur. J. 12 (2006) 2263-2269
20. Choi K., and Hamilton A.D. Coord. Chem. Rev. 240 (2003) 101-110
21. Hartley J.H., James T.D., and Ward C.J. J. Chem. Soc., Perkin Trans. 1 (2000) 3155-3184
22. Lee C.H., Lee J.S., Na H.K., Yoon D.W., Miyji H., Cho W.S., and Sessler J.L. J. Org. Chem. 70 (2005) 2067-2074
23. Mizukami S., Nagano T., Urano Y., Odani A., and Kikuchi K. J. Am. Chem. Soc. 124 (2002) 3920-3925
24. Otón F., Tárraga A., Velasco M.D., Espinosa A., and Molina P. Chem. Commun. (2004) 1658-1659
25. Anzenbacher Jr. P., Try C.A., Miyaji H., Jursíková K., Lynch V.M., Marquez M., and Sessler J.L. J. Am. Chem. Soc. 122 (2000) 10268-10272
26. Lu H., Xu W., Zhang D., and Zhu D. Chem. Commun. (2005) 4777-4779
27. Curiel D., Beer P.D., Cowley A., Sambrook M.R., and Szemes F. Chem. Commun. (2004) 1162-1163
28. Li Z.-B., Lin J., Zhang H.-C., Sabat M., Hyacinth M., and Pu L. J. Org. Chem. 69 (2004) 6284-6293
29. Cho E.J., Moon J.W., Ko S.W., Lee J.Y., Kim S.K., Yoon J., and Nam K.C. J. Am. Chem. Soc. 125 (2003) 12376-12377
30. Curiel D., Cowley A., and Beer P.D. Chem. Commun. (2005) 236-238
31. Amendola V., Boiocchi D., Colasson B., and Fabbrizzi L. Inorg. Chem. 45 (2006) 6138-6147
32. Amendola V., Esteban-goä mez D., Fabbrizzi L., and Licchelli M. Acc. Chem. Res. 39 (2006) 343-353
33. Lin Z.-H., Ou S.-J., Duan C.-Y., Zhang B.-G., and Bai Z.-P. Chem Commun. (2006) 624-626
34. Gale P.A. Chem. Commun. (2005) 3761-3763
35. Xu S., Chen K.C., and Tian H. J. Mater. Chem. (2005) 2676-2680
36. Boioccho M., Boca D.L., Gomez D.E., Fabbrizzi L., Licchelli M., and Monzani E. Chem.-Eur. J. 11 (2005) 3097-3104
37. Evgeny A.K., DanPantos G., Reshetova M.D., Khrustalev V.N., Lynch V.M., Ustynyuk Y.A., and Sessler J.L. Angew. Chem., Int. Ed. 44 (2005) 7386-7390
38. Nielsen K.A., Cho W.-S., Lyskawa J., Levillain E., Lynch V.M., Sessler J.L., and Jeppesen J.O. J. Am. Chem. Soc. 128 (2006) 2444-2451 and reference cited therein
39. Peng X., Wu Y., Fan J., Tian M., and Han K. J. Org. Chem. 70 (2005) 10524-10531
40. Jose D.A., Kumar D.K., Ganguly B., and Das A. Org. Lett. 6 (2004) 3445-3448
41. Jose D.A., Kumar D.K., Ganguly B., and Das A. Tetrahedron Lett. 46 (2005) 5343-5346
42. Jose D.A., Singh A., Ganguly B., and Das A. Tetrahedron Lett. 48 (2007) 3695-3698
43. Gomez D.E., Fabbrizi L., Licchelli M., and Monzani E. Org. Biomol. Chem. 3 (2005) 1495-1500
44. Bordwell F.G. Acc. Chem. Res. 21 (1988) 456-463
45. Kwon J.Y., Singh N.J., Kim H., Kim S.K., and Yoon J. J. Am. Chem. Soc. 126 (2004) 8892-8893
46. Kwon J.Y., Jang Y.J., Kim S.K., Lee K.-H., Kim J.S., and Yoon J. J. Org. Chem. 69 (2004) 5155-5157
47. Kim Y.-J., Kwak H., Lee S.J., Lee J.S., Kwon H.J., Nam S.H., Lee K., and Kim C. Tetrahedron 62 (2006) 9635-9640
48. Gunnlaugsson T., Davis A.P., O'Brien J.E., and Glynn M. Org. Lett. 4 (2002) 2449-2452
49. Boiocchi M., Boca L.D., Gomez D.E., Fabbrizzi L., Licchelli M., and Monzani E. J. Am. Chem. Soc. 126 (2004) 16507-16514
50. Evans L.S., Gale P.A., Light M.E., and Quesada R. Chem. Commun. (2006) 965-967
51. Ghosh T., Maiya B.G., and Wong M.W. J. Phys. Chem. A 108 (2004) 11249-11259
52. TITAN; Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612, USA, Schrodinger, Inc., 1500 SW First Avenue, Suite 1180, Portland, OR 97201, USA;
53. The interaction energy is obtained by the energy of the complex subtracted from the sum of the constituent energies. The interaction is very strong due to charged hydrogen bonds. Thus, the basis set superposition error (BSSE) is expected to be negligible compared to the magnitude of the total interaction energies.
54. One can find further support from the fact that there should be higher overlap in the red shifted absorption band for the naphthalene unit adjacent to the deprotonated urea derivative and the emission band for the nitrobenzene unit as compared to that of the corresponding urea derivative before deprotonation.
55. Inoue H., Hida M., Nakashima N., and Yoshihara K. J. Phys. Chem. 86 (1982) 3184-3188
56. Yatsuhashi T., Nakajima Y., Shimada T., and Inoue H. J. Phys. Chem. A 102 (1998) 3018-3024
57. SAINT+, 6.02 ed (1999), Bruker AXS, Madison, WI
58. Sheldrick M. SHELXTL Reference Manual, Version 5.1 (1997), Bruker AXS, Madison, WI
59. Sheldrick G.M. SHELXL-97: Program for Crystal Structure Refinement (1997), University of Göttingen, Göttingen, Germany
60. Mercury 1.4.1 Supplied with Cambridge Structural Database, Copyright CCDC, 2005-2006.
61. Perisamy N., Doraiswamy S., Maiya G.B., and Venkataraman B. J. Chem. Phys. 88 (1988) 1638-1651
62. Bevington P.R. Data Reduction and Error Analysis for the Physical Sciences (1969), McGraw-Hill, New York, NY