Hydrogen bond energies and cooperativity in substituted calix[ n ]arenes (n = 4, 5)

Journal of Physical Chemistry A

Volumn 116, Issue 14, 2012, Pages 3739-3744

  Khedkar, Jayshree K ^a   Deshmukh, Milind M ^b   Gadre, Shridhar R ^c   Gejji, Shridhar P ^a  

^a UNIVERSITY OF PUNE   (India)

^b KYOTO UNIVERSITY   (Japan)

^c INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BOND CRITICAL POINTS; COOPERATIVITY; ELECTRON-DONATING GROUP; HYDROGEN BOND ENERGY; HYDROGEN BONDING NETWORK; MOLECULAR TAILORING; QUANTUM THEORY OF ATOMS IN MOLECULES;

AROMATIC COMPOUNDS; QUANTUM THEORY;

HYDROGEN BONDS;

EID: 84859794620     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp3006519     Document Type: Article

References (61)

1. Szejtli, J. Chem. Rev. 1998, 98, 1743-1753
2. Kim, J.; Jung, I. -S.; Kim, S. -Y.; Lee, E.; Kang, J. -K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540-541
3. Shinkai, S. Tetrahedron 1993, 49, 8933-8968
4. Gutsche, C. D. Monographs in Supramolecular Chemistry; Vol. 1. Calixarenes; The Royal Society of Chemistry: Cambridge, U.K., 1989.
5. Gutsche, C. D. Monographs in Supramolecular Chemistry; Vol. 6. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, U.K., 1998.
6. Vrielynck, L.; Lapouge, C.; Marquis, S.; Kister, J.; Dupuy, N. Spectrochim. Acta, A 2004, 60, 2553-2559
7. Al-Shihry, S. S Spectrochim. Acta, A 2005, 61, 2439-2443
8. Liu, J. -X.; Long, L. -S.; Huaang, R. -B. L.; Zheng, L. -S. Inorg. Chem. 2007, 46, 10168-10173
9. Buschmann, H. -J.; Cleve, E.; Jansen, K.; Wego, A.; Schollmeyer, E. J. Inclusion Phenom. Macrocyclic Chem. 2001, 40, 117-120
10. Vicens, J.; Böhmer, V. Calixarenes: A Versatile Class of Macrocyclic Compounds; Kluwer Academic Publishers: Dordrecht, The Netherlands, Boston, MA, 1991.
11. Furer, V. L.; Borisoglebskaya, E. I.; Zverev, V. V.; Kovalenko, V. I. Spectrochim. Acta, A 2005, 62, 483-493
12. Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, U.K., 1998.
13. Pinjari, R. V.; Joshi, K. A.; Gejji, S. P. J. Phys. Chem. A 2006, 110, 13073-13080
14. Pinjari, R. V.; Joshi, K. A.; Gejji, S. P. J. Phys. Chem. A 2007, 111, 13583-13589
15. Pinjari, R. V.; Khedkar, J. K.; Gejji, S. P. J. Inclusion Phenom. Macrocyclic Chem. 2010, 66, 371-380
16. Pinjari, R. V.; Gejji, S. P. J. Phys. Chem. A 2008, 112, 12679-12686
17. Saenger, W.; Steiner, T. Acta Crystallogr., A 1998, A54, 798-805
18. Novikov, A. N.; Shapiro, Y. E. J. Phys. Chem. A 2012, 116 (1) 546-559
19. Keutsch, F. N.; Cruzan, J. D.; Saykally, R. J. Chem. Rev. 2003, 103, 2533-2578
20. Cockroft, S. L.; Hunter, C. A.; Lawso, K. R.; Perkins, J.; Urch, C. J. J. Am. Chem. Soc. 2005, 127, 8594-8595
21. Hobza, P.; Havlas, Z. Chem. Rev. 2000, 100, 4253-4264
22. Klein, R. A. J. Phys. Chem. A 2004, 108, 5851-5863
23. Deshmukh, M. M.; Gadre, S. R.; Bartolotti, L. J. J. Phys. Chem. A 2006, 110, 12519-12523
24. Deshmukh, M. M.; Bartolotti, L. J; Gadre, S. R. J. Phys. Chem. A 2008, 112, 312-321
25. Deshmukh, M. M.; Gadre, S. R. J. Phys. Chem. A 2009, 113, 7927-7932
26. Deshmukh, M. M.; Bartolotti, L. J; Gadre, S. R. J. Comput. Chem. 2011, 32, 2996-3004
27. Saenger, W. Nature 1979, 279, 343-344
28. Del Bene, J. E.; Pople, J. A. J. Chem. Phys. 1970, 52, 4858-4866
29. Lang, J.; Deckerova, V.; Czernek, J.; Lhotak, P. J. Chem. Phys. 2005, 122, 044506-044511
30. Michl, J., Ed., Chem. Rev. 1998, 98, 1741-2076 (A Special Issue on Cyclodextrins).
31. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875-1917
32. Lipkowitz, K. B. Chem. Rev. 1998, 98, 1829-1873
33. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745
34. Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734
35. Suwattanamala, A.; Magalhaes, A. L.; Gomes, J. A. N. F. J. Mol. Struct.: THEOCHEM 2005, 729, 83-90
36. Iki, N.; Kumagai, H.; Morohashi, N.; Ejima, K.; Hasegawa, M.; Miyanari, S.; Miyano, S. Tetrahedron Lett. 1998, 39, 7559-7562
37. Mislin, G.; Graf, E.; Hosseini, M. W.; De Cian, A.; Fischer, J. Chem. Commun. 1998, 1345-1346
38. Rudkevich, D. M. Chem. - Eur. J. 2000, 6, 2679-2686
39. Frank, H. S.; Wen, W. Y. Discuss. Faraday Soc. 1957, 24, 133-140
40. Huyskens, P. L. J. Am. Chem. Soc. 1977, 99, 2578-2582
41. Parra, R. D.; Gong, B.; Zeng, X. C. J. Chem. Phys. 2001, 115, 6036-6041
42. Kleeberg, H.; Klein, D.; Luck, W. A. P. J. Phys. Chem. 1987, 91, 3200-3203
43. Scheiner, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: New York, 1997; Chapter 5 and references therein.
44. Iki, N.; Kabuto, C.; Fukishima, T.; Kumagai, H.; Takeya, H.; Miyanari, S.; Miyashi, T.; Miyano, S. Tetrahedron 2000, 56, 1437-1743
45. Katsyuba, S.; Kovalenko, V.; Chernova, A.; Vandyukova, E.; Zverev, V.; Shagidullin, R.; Antipin, I.; Solovieva, S.; Stoikov, I.; Konovalov, A. Org. Biomol. Chem. 2005, 3 (14) 2558-2565
46. Kovalenko, V. I.; Maklakov, L. I.; Borisoglebskaya, E. I.; Potapova, L. I.; Shokova, E. A.; Vatsouro, I. M.; Kovalev, V. V. Russ. Chem. Bull., Int. Ed. 2007, 56 (6) 1103-1109
47. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
48. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
49. Frisch, M. J.; Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
50. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, U.K., 1990.
51. Matta, D. F.; Boyd, R. J. The quantum theory of atoms in molecules. In An Introduction to the Quantum Theory of Atoms in Molecules; Matta, D. F.; Boyd, R. J., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 1-34.
52. Limaye, A. C.; Gadre, S. R. Curr. Sci. 2001, 80, 1298-1301
53. Kovalenko, V. I.; Chernova, A. V.; Borisoglebskaya, E. I.; Syuba, S. A.; Zverev, V. V.; Shagidullin, R. R.; Antipin, I. S.; Solovieva, S. E.; Stoikov, I. I.; Konovalov, A. I. Russ. Chem. Bull., Int. Ed. 2002, 51, 825-827
54. Groenen, L. C.; Steinwender, E.; Lutz, B. T. G.; Vander Maas, J. H.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 1992, 2, 1893-1898
55. Bernardino, R. J.; Cabral, B. J. C. J. Phys. Chem. A 1999, 103, 9080-9085
56. Bernardino, R. J.; Cabral, B. J. C. J. Mol. Struct.: THEOCHEM 2001, 549, 253-260
57. Khedkar, J. K.; Pinjari, R. V.; Gejji, S. P. J. Phys. Chem. A 2011, 115, 10624-10637
58. Böhmer, V.; Goldmann, H.; Vogt, W.; Paulus, E. F.; Tobiason, F. L.; Thielman, M. J. J. Chem. Soc., Perkin Trans. 1990, 2, 1769-1775
59. Kleeberg, H.; Luck, W. A. P. Z. Phys. Chem. (Leipzig) 1989, 270, 613-625
60. Furer, V. L.; Borisoglebskaya, E. I.; Kovalenko, V. I. Spectrochim. Acta, A 2005, 61 (1-2) 355-359
61. Amiri, A.; Babaeie, F.; Monajjemi, M. Phys. Chem. Liq. 2008, 46 (4) 379-389