Dihydrogen phosphate as a hydrogen-bonding donor element: Anion receptors based on acylhydrazone

Journal of Organic Chemistry

Volumn 78, Issue 23, 2013, Pages 12121-12127

  Pandian, T Senthil ^a   Cho, Seung Joo ^b   Kang, Jongmin ^a  

^a Sejong University   (South Korea)

^b Chosun University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ASSOCIATION CONSTANT; BINDING AFFINITIES; BINDING CONSTANT; COMPLEX STRUCTURE; DIHYDROGEN PHOSPHATE; ORDERS OF MAGNITUDE; POLAR SOLVENTS; SELECTIVE RECEPTORS;

AROMATIC COMPOUNDS; BINDING ENERGY; HYDROGEN BONDS; NITROGEN;

IONS;

ACYLHYDRAZONE; ANION; DIHYDROGEN PHOSPHATE; HYDRAZONE DERIVATIVE; HYDROGEN; NITROGEN; OXYGEN; PHOSPHATE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYST; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; COVALENT BOND; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

ANIONS; HYDRAZONES; HYDROGEN; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHATES;

EID: 84890232262     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402103d     Document Type: Article

References (56)

1. Jose, D. A.; Kar, P.; Koley, D.; Ganguly, B. Inorg. Chem. 2007, 46, 5576
2. Velu, R.; Ramakrishnan, V. T.; Ramamurthy, P. J. Photochem. Photobiol., A 2011, 217, 313
3. Kim, S.-H; Hwang, I.-J.; Gwon, S.-Y.; Burkinshaw, S. M.; Son, Y. A. Dyes Pigm. 2011, 88, 84
4. Yang, W.; Yin, Z.; Li, Z.; He, J.; Cheng, J.-P. J. Mol. Struct. 2008, 889, 279
5. Sessler, J. L.; Cho, D. G.; Lynch, V. J. Am. Chem. Soc. 2006, 128, 16518
6. Shao, J.; Yu, X.; Xu, X.; Lin, H.; Cai, Z.; Lin, H. K. Talanta 2009, 79, 547
7. Yang, Z.; Zhang, K.; Gong, F.; Li, S.; Chen, J.; Ma, J. S.; Sobenina, L. N.; Mikhaleva, A. I.; Trofimov, B.A.; Yang, G. J. Photochem. Photobiol., A 2011, 217, 29
8. Suksai, C.; Tuntulani, T. Chem. Soc. Rev. 2003, 32, 192
9. Gunnlaugsson, T.; Glynn, M.; Tocci, G. M.; Kruger, P. E.; Pfeffer, F. M. Coord. Chem. Rev. 2006, 250, 3094
10. O'Neil, E. J.; Smith, B. D. Coord. Chem. Rev. 2006, 250, 3068
11. Beer, P. D.; Bayly, S. R. Top. Curr. Chem. 2005, 255, 125
12. Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419
13. Sessler, J. L.; Cho, D. G.; Lynch, V. J. Am. Chem. Soc. 2006, 128, 16518
14. Furman, P. A.; Fyfe, J. A.; St. Clair, M. H.; Weinhold, K.; Rideout, J. L.; Freeman, G. A. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 8333
15. Kral, V.; Sessler, J. L. Tetrahedron 1995, 51, 539
16. Ojida, A.; Mito-oka, Y.; Sada, K.; Hamachi, I. J. Am. Chem. Soc. 2004, 126, 2454
17. Gale, P. A. Chem. Commun. 2005, 30, 3761
18. Mathews, C. K.; van Holde, K. E. Biochemistry; Benjamin Cummings Publishing Co., Inc.: Redwood City, CA, 1990.
19. Ronaghi, M.; Karamohamed, S.; Pettersson, B.; Uhlen, M.; Nyren, P. Anal. Biochem. 1996, 242, 84
20. Xu, S.; He, M.; Yu, H.; Cai, X.; Tan, X.; Lu, B.; Shu, B. Anal. Biochem. 2001, 299, 188
21. Lopacinska, K. D.; Strosznajder, J. B. J. Physiol. Pharmacol. 2005, 56, 15
22. Kamenetsky, M.; Middelhaufe, S.; M. Bank, E.; Levin, L. R.; Buck, J.; Steegborn, C. J. Mol. Biol. 2006, 362, 623
23. Lee, G. W.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2008, 49, 1952
24. Shao, J.; Lin, H.; Shang, X. F.; Chen, H. M.; Lin, H. K. J. Inclusion Phenom. Macrocyclic Chem. 2007, 59, 371
25. Jimenez Blanco, J. L.; Bootello, P.; Benito, J. M.; Ortiz Mellet, C. J.; Garcia Fernandez, M. J. Org. Chem. 2006, 71, 5136
26. Jose, D. A.; Mishra, S.; Ghosh, A.; Shrivastav, A.; Mishra, S. K.; Das, A. Org. Lett. 2007, 9, 1979
27. Llinares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57
28. Bondy, C. R.; Loeb, S. J. Coord. Chem. Rev. 2003, 240, 77
29. Ilioudis, C. A.; Steed, J. W. J. Supramol. Chem. 2001, 1, 165
30. In, S.; Cho, S. J.; Lee, K. H.; Kang, J. Org. Lett. 2005, 7, 3993
31. Castellano, R. K. Curr. Org. Chem. 2004, 8, 845
32. Ilioudis, C. A.; Tocher, D. A.; Steed, J. W. J. Am. Chem. Soc. 2004, 126, 12395
33. Turner, D. R.; Spencer, E. C.; Howard, J. A. K.; Tocher, D. A.; Steed, J. W. Chem. Commun. 2004, 1352
34. Chmielewski, M. J.; Charon, M.; Jurczak, J. Org. Lett. 2004, 6, 3501
35. Kang, S. O.; VanderVelde, D.; Powell, D.; Bowman-James, K. J. Am. Chem. Soc. 2004, 126, 12272
36. Kwon, J. Y.; Jang, Y. J.; Kim, S. K.; Lee, K.-H.; Kim, J. S.; Yoon, J. J. Org. Chem. 2004, 69, 5155
37. Costero, A. M.; Banuls, M. J.; Aurell, M. J.; Ward, M. D.; Argent, S. Tetrahedron 2004, 60, 9471
38. Ghosh, S.; Choudhury, A. R.; Row, T. N. G.; Maitra, U. Org. Lett. 2005, 7, 1441
39. Metzger, S.; Lippert, B. J. Am. Chem. Soc. 1996, 118, 12467
40. Auffinger, P.; Louise-May, S.; Westof, E. J. Am. Chem. Soc. 1996, 118, 1181
41. Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290
42. Steiner, T.; Saenger, W. J. Am. Chem. Soc. 1992, 114, 10146
43. Sharma, C. V. K.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 1994, 2, 2345
44. Chaney, J. D.; Goss, C. R.; Folting, K.; Santarsiero, B. D.; Hollingworth, M. D. J. Am. Chem. Soc. 1996, 118, 9432
45. Iwasawa, T.; Hooley, R. J.; Rebek, J., Jr. Science 2007, 317, 493
46. Zhao, H.; Burke, T. R., Jr. Tetrahedron 1997, 53, 4219
47. Khan, K. M. Bioorg. Med. Chem. 2003, 11, 1381
48. Benesi, H.; Hildebrand, H. J. Am. Chem. Soc. 1949, 71, 2703
49. Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311
50. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
51. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
52. Simon, S.; Duran, M.; Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024
53. Bader, R. F. W. Acc. Chem. Res. 1975, 8, 34
54. Keith, T. A. AIMAll, version 13.05.06; TK Gristmill Software: Overland Park, KS, 2013.
55. Koch, U.; Popelier, L. A. J. Phys. Chem. 1995, 99, 9747
56. Tang, T. H.; Hu, W. J.; Yan, D. Y.; Cui, Y. P. J. Mol. Struct. 1990, 207, 319 Foundation