Blue shifting C-H⋯O hydrogen bonded complexes between chloroform and small cyclic ketones: Ring-size effects on stability and spectral shifts

Journal of Physical Chemistry A

Volumn 113, Issue 13, 2009, Pages 3078-3087

  Mukhopadhyay, Anamika ^a   Mukherjee, Moitrayee ^a   Pandey, Prasenjit ^a   Samanta, Amit K ^a   Bandyopadhyay, Biman ^a   Chakraborty, Tapas ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; BLUE SHIFTING; BLUE SHIFTS; CARBONYL GROUPS; CARBONYL OXYGENS; CYCLIC KETONES; CYCLOBUTANONE; CYCLOHEXANONE; CYCLOPENTANONE; DONOR ACCEPTORS; FT-IR SPECTROSCOPIES; HYDROGEN BOND ACCEPTORS; HYDROGEN-BONDED COMPLEXES; HYPERCONJUGATION; INTERMOLECULAR INTERACTION ENERGIES; ISOSBESTIC POINTS; NBO ANALYSIS; NET EFFECTS; PROTON AFFINITIES; QUANTUM-MECHANICAL CALCULATIONS; RED-SHIFTED; RELATIVE STABILITIES; RING SIZES; ROOM TEMPERATURES; SIZE EFFECTS; SPECTRAL ANALYSIS; SPECTRAL SHIFTS; TRANSITION INTENSITIES;

BINDING ENERGY; BINDING SITES; CARBONYLATION; CHARGE TRANSFER; CHLORINE COMPOUNDS; ELECTRIC FIELDS; ELECTRONIC STRUCTURE; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN; HYDROGEN BONDS; ION EXCHANGE; KETONES; MECHANISMS; OXYGEN; SPECTRUM ANALYZERS; STOICHIOMETRY;

COMPLEXATION;

EID: 63849282622     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp900473w     Document Type: Article

References (70)

1. Sutor, D. J. Nature 1962, 195, 68.
2. Buckingham, A. D.; Del Bene, J. E.; McDowell, S. A. C. Chem. Phys. Lett. 2008, 463, 1, and references therein.
3. Joseph, J.; Jemmis, E. D. J. Am. Chem.Soc. 2007, 129, 4620, and references therein.
4. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond; Oxford University Press: Oxford, 1999.
5. Scheiner, S. Hydrogen Bonding; Oxford University Press: New York, 1997.
6. Jiang, L.; Lai, L. J. Biol. Chem. 2002, 277, 37732.
7. Senes, A.; Ubarretxena-Belandia, I.; Engelman, D. M. Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 9056.
8. Weiss, M. S.; Brandl, M.; Sühnel, J.; Pal, D.; Hilgenfeld, R. Trends Biochem. Sci. 2001, 26, 521.
9. Brandl, M.; Meyer, M.; Sühnel, J. J. Biomol. Struct. Dyn. 2001, 18, 545.
10. Scheiner, S.; Kar, T.; Gu, Y. J. Biol. Chem. 2001, 276, 9832.
11. Ornstein, R. L.; Zheng, Y. J. J. Biomol. Struct. Dyn. 1997, 14, 657.
12. Berger, I.; Egli, M.; Rich, A. Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 12116.
13. Takahara, P. M.; Frederick, C. A.; Lippard, S. J. J. Am. Chem. Soc. 1996, 118, 12309.
14. Egli, M.; Gessner, R. V. Proc. Natl. Acad. Sci. U. S. A. 1995, 92, 180.
15. Derewenda, Z. S.; Lee, L.; Derewenda, U. J. Mol. Biol. 1995, 252, 248.
16. Dozova, N.; Krim, L.; Alikhani, M. E.; Lacome, N. J. Phys. Chem. A 2005, 109, 10273.
17. Delanoye, S. N.; Herrebout, W. A.; van der Veken, B. J. J. Am. Chem.Soc. 2002, 124, 7490.
18. Delanoye, S. N.; Herrebout, W. A.; van der Veken, B. J. J. Am. Chem.Soc. 2002, 124, 11854.
19. Melikova, S. M.; Rutkowski, K. S.; Rodziewicz, P.; Koll, A. Chem. Phys. Lett. 2002, 352, 301.
20. van der Veken, B. J.; Herrebout, W. A.; Szostak, R.; Shchepkin, D. N.; Havlas, Z.; Hobza, P. J. Am. Chem. Soc. 2001, 123, 12290.
21. Boldeskul, I. E.; Tsymbal, I. F.; Ryltsev, E. V.; Latajka, Z.; Barnes, A. J. J. Mol. Struct. 1997, 436, 167.
22. McDowell, S. A. C; Buckingham, A. D. J. Am. Chem. Soc. 2005, 127, 15515.
23. McDowell, S. A. C.; Buckingham, A. D. Spectrochim. Acta, Part A 2005, 61, 1603.
24. Herrebout, W. A.; Delanoye, S. N.; van der Veken, B. J. J. Phys. Chem. A 2004, 108, 6059.
25. Barnes, A. J. J. Mol. Struct. 2004, 704, 3.
26. Mrázková, E.; Hobza, P. J. Phys. Chem. A 2003, 107, 1032.
27. Alabugin, I. V.; Manoharan, M.; Peabody, S.; Weinhold, F. J. Am. Chem. Soc. 2003, 125, 5973.
28. McDowell, S. A. C. Phys. Chem. Chem. Phys. 2003, 5, 808.
29. Li, X.; Liu, L.; Schlegel, H. B. J. Am. Chem. Soc. 2002, 124, 9639.
30. Hobza, P.; Havlas, Z. Theor. Chem. Acc. 2002, 108, 325.
31. Hermansson, K. J. Phys. Chem. A 2002, 106, 4695.
32. Hobza, P.; Havlas, Z Chem. Rev. 2000, 100, 4253, and references therein.
33. Scheiner, S. Adv. Mol. Struct. Res. 2000, 6, 159.
34. Scheiner, S.; Gu, Y.; Kar, T. J. Mol. Struct. (THEOCHEM) 2000, 500, 441.
35. Hobza, P.; Havlas, Z. Chem. Phys. Lett. 1999, 303, 447.
36. Hobza, P.; Spirko, V.; Havlas, Z.; Buchhold, K.; Reimann, B.; Barth, H. D.; Brutschy, B. Chem. Phys. Lett. 1999, 299, 180.
37. Caminati, W.; Melandri, S.; Moreschini, P.; Favero, P. G. Angew. Chem., Int. Ed. Engl. 1999, 38, 2924.
38. Gu, Y.; Kar, T.; Scheiner, S. J. Am. Chem.Soc. 1999, 121, 9411.
39. Venkatesan, V.; Fujii, A.; Ebata, T.; Mikami, N. Chem. Phys. Lett. 2004, 394, 45.
40. Rigby, M.; Smith, E. B.; Wakeham, W. A.; Maitland, G. C. The Forces Between Molecules; Oxford University Press: New York, 1986.
41. Scheiner, S.; Kar, T. J. Phys. Chem. A 2002, 106, 1784.
42. Scheiner, S.; Grabowski, S. J.; Kar, T. J. Phys. Chem. A 2001, 105, 10607.
43. Dykstra, C. E. Acc. Chem. Res. 1988, 21, 355, and references therein.
44. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
45. Ratajczak, H. J. Phys. Chem. 1972, 76, 3000.
46. Stone, A. J.; Fowler, P. W.; Buckingham, A. D. J. Chem. Phys. 1997, 107, 1030.
47. Zierkiewicz, W.; Jurečka, P.; Hobza, P. Chem. Phys. Chem. 2005, 6, 609.
48. Kryachko, E. S.; Karpfen, A. Chem. Phys. 2006, 329, 313.
49. Karpfen, A.; Kryachko, E. S. J. Phys. Chem. A 2005, 109, 8930.
50. Qian, W.; Krimm, S. J. Phys. Chem. A 2005, 109, 5608.
51. Qian, W.; Krimm, S. J. Phys. Chem. A 2002, 106, 11663.
52. Qian, W.; Krimm, S. J. Phys. Chem. A 2002, 106, 6628.
53. Masunov, A.; Dannenberg, J. J.; Contreras, R. H. J. Phys. Chem. A 2001, 105, 4737.
54. Parish, C. A.; Dykstra, C. E. J. Phys. Chem. 1993, 97, 9374.
55. Hermansson, K. J. Chem. Phys. 1993, 99, 861.
56. Liu, S. Y.; Dykstra, C. E. Chem. Phys. Lett. 1987, 136, 22.
57. Liu, S. Y.; Dykstra, C. E.; Malik, D. J. Chem. Phys. Lett. 1986, 130, 403.
58. Pluháčkovǎ, K.; Hobza, P. Chem. Phys. Chem. 2007, 8, 1352.
59. Wang, J. T.; Feng, Y.; Liu, L.; Li, X. S.; Guo, Q. X. Chem. Lett. 2003, 32, 746.
60. Alabugin, I. V.; Manoharan, M.; Weinhold, F. A. J. Phys. Chem. A 2004, 108, 4720.
61. Silverstein, R. M.; Webster, F. X.; Kiemle, D. Sectrometric Identification of Organic Compounds; Wiley: New York, 2005.
62. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
63. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
64. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
65. Frisch, M. J.; et al. Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
66. Bent, H. A. Chem. Rev. 1961, 61, 275.
67. Alabugin, I. V.; Manoharan, M. J. Comput. Chem. 2007, 28, 373.
68. Pimental, G. C.; Mcclella, A. L. Annu. Rev. Phys. Chem. 1971, 22, 347.
69. Kartha, V. B.; Mantsch, H. H.; Jones, R. N. Can. J. Chem. 1973, 51, 1749.
70. Fuhrer, H.; Kartha, V. B.; Krueger, P. J.; Mantsch, H. H.; Jones, R. N. Chem. Rev. 1972, 72, 439.