Influence of substitution on the strength and nature of CH⋯N hydrogen bond in XCCH⋯NH3 complexes

International Journal of Quantum Chemistry

Volumn 111, Issue 5, 2011, Pages 961-969

  Roohi, Hossein ^a,b   Bagheri, Sotoodeh ^b  

^a UNIVERSITY OF GUILAN   (Iran)

^b UNIVERSITY OF SISTAN AND BALUCHESTAN   (Iran)

Author keywords

Ab initio calculations; AIM; CH N hydrogen bond; NBO; NMR

Indexed keywords

ATOMS; BINDING ENERGY; CALCULATIONS; CHLORINE COMPOUNDS; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; QUANTUM THEORY;

AB INITIO CALCULATIONS; EFFECT OF SUBSTITUTION; ELECTRONEGATIVE ATOMS; INTERACTION CHARACTERISTICS; INTERACTION ENERGIES; NATURAL BOND ORBITAL ANALYSIS; QUANTUM CHEMICAL CALCULATIONS; QUANTUM THEORY OF ATOMS IN MOLECULES;

COMPLEXATION;

EID: 79551572834     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.22460     Document Type: Article

References (66)

1. Latimer, W. M., Rodebush, W. H., J Am Chem Soc 1920, 42, 1419.
2. Jeffrey, G. A., Saenger, W., Hydrogen Bonding in Biological Structures; Springer: Berlin, 1991.
3. Dunitz, J. D., X-ray Analysis and the Structure of Organic Molecules; Cornell University Press: Ithaca, 1979.
4. Desiraju, G. R., Crystal Engineering, The Design of Organic Solids; Elsevier: Amsterdam, 1989, p 142.
5. Pimentel, G. C., McClellan, A. L., The Hydrogen Bond; Freeman: San Francisco, CA, 1960.
6. Jeffrey, G. A., Saenger, W., Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
7. Scheiner, S., Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: New York, 1997.
8. Desiraju, G. R., Acc Chem Res 1996, 29, 441.
9. Kariuki, B. M., Harris, K. D. M., Philp, D., Robinson, J. M. A., J Am Chem Soc 1997, 119, 12679.
10. Robinson, J. M. A., Philp, D., Kariuki, B. M., Harris, K. D. M., Chem Commun 1999, 329.
11. Gu, J., Kar, T., Scheiner, S., J Am Chem Soc 1999, 121, 9411.
12. Scheiner, S., Gu, Y., Kar, T., J Mol Struct 2000, 500, 441.
13. Al-Juaid, S. S., Al-Nasr, A. K. A., Eaborn, C., Hitchcock, P. B., J Chem Soc Chem Commun 1991, 1482.
14. Hanton, L. R., Hunter, C. A., Purvis, D. H., J Chem Soc Chem Commun 1992, 1134.
15. Viswamitra, M. A., Radhakrishnan, R., Bandekar, J., Desiraju, G. R., J Am Chem Soc 1993, 115, 4868.
16. Allen, F. H., Howard, J. A. K., Hoy, V. J., Desiraju, G. R., Reddy, D. S., Wilson, C. C., J Am Chem Soc 1996, 118, 4081.
17. Allen, F. H., Hoy, V. J., Howard, J. A. K., Thalladi, V. R., Desiraju, G. R., Wilson, C. C., McIntyre, G. J., J Am Chem Soc 1997, 119, 3477.
18. Grabowski, S. J., J Chem Res (S) 1996, 12, 534.
19. Grabowski, S. J., Wilamowski, J., Osman, D., Sepiol, J. J., Rodier, N., Aust J Chem 1996, 49, 951.
20. Platts, J. A., Howard, S. T., Woźniak, K., Chem Commun 1996, 63.
21. Ahlberg, P., Davidsson, Ö., Löwendahl, M., Hilmersson, G., Karlsson, A., HÃ¥kansson, M., J Am Chem Soc 1997, 119, 1745.
22. Robinson, J. M. A., Kariuki, B. M., Gough, R. J., Harris, K. D. M., Philp, D., J Solid State Chem 1997, 134, 203.
23. Robinson, J. M. A., Kariuki, B. M., Harris, K. D. M., Philp, D., J Chem Soc Perkin Trans 2 1998, 2459.
24. Philp, D., Robinson, J. M. A., J Chem Soc Perkin Trans 2 1998, 1643.
25. Crabtree, R. H., Siegbahn, P. E. M., Eisenstein, O., Rheingold, A. L., Koetzle, T. F., Acc Chem Res 1996, 29, 348.
26. Richardson, T. B., Koetzle, T. F., Crabtree, R. H., Inorg Chim Acta 1996, 250, 69.
27. Liu, Q., Hoffman, R., J Am Chem Soc 1995, 117, 10108.
28. Orlowa, G., Scheiner, S., J Phys Chem A 1998, 102, 260.
29. Orlowa, G., Scheiner, S., Kar, T., J Phys Chem A 1999, 103, 514.
30. Alkorta, I., Elguero, J., Foces-Foces, C., Chem Commun 1996, 1633.
31. Popelier, P. L. A., J Phys Chem A 1998, 102, 1873.
32. Grabowski, S., J Chem Phys Lett 1999, 312, 542.
33. Grabowski, S., J Chem Phys Lett 2000, 327, 203.
34. Grabowski, S. J., J Mol Struct 2000, 553, 151.
35. Del Bene, J. E., In Encyclopedia of Computational Chemistry;, Schleyer, P. V. R., Allinger, N. L., Clark, T., Gasteiger, J., Kollman, P., Schaefer, H. F., III, Shreiner, P. R., Eds.; Wiley: Chichester, 1998; p 1263.
36. Alkorta, I., Rozas, I., Elguero, J., Chem Soc Rev 1998, 27, 163.
37. Desiraju, G. R., Steiner, T., The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: New York, 1999.
38. Hartmann, M., Wetmore, S. D., Radom, L., J Phys Chem A 2001, 105, 4470.
39. Rovira, M. C., Novoa, J. J., Whangbo, M. H., Williams, J. M., Chem Phys 1995, 200, 319.
40. Taylor, R., Kennard, O., J Am Chem Soc 1982, 104, 5063.
41. Reddy, D. S., Goud, B. S., Panneerselvam, K., Desiraju, G. R., J Chem Soc Chem Commun 1993, 663.
42. Reddy, D. S., Craig, D. C., Desiraju, G. R., J Am Chem Soc 1996, 118, 4090.
43. Hartman, M., Radom, L., J Phys Chem A 2000, 104, 968.
44. Wetmore, S. D., Schofield, R., Smidt, D. M., Radom, L., J Phys Chem A 2001, 105, 8718.
45. Dimitrova, V., Ilieva, S., Galabov, B., J Phys Chem A 2002, 106, 11801.
46. Galabov, B., Bobadova-Parvanova, P., IIieva, S., Dimitrova, V., J Mol Struct 2003, 630, 101.
47. Kryachko, E. S., Scheiner, S., J Phys Chem A 1940, 2008, 112.
48. Bader, R. F. W., Atoms in Molecules. A Quantum Theory; Oxford University Press: Oxford, New York, 1990.
49. Reed, A. E., Curtiss, L. A., Weinhold, F., Chem Rev 1988, 88, 899.
50. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., Pople, J. A., Gaussian 03, Revision B. 03; Gaussian, Inc.: Pittsburgh, PA, 2003.
51. Moller, C., Plesset, M. S., Phys Rev 1934, 46, 618.
52. Boys, S. F., Bernadi, F., Mol Phys 1970, 19, 553.
53. Ditchfield, R., Mol Phys 1974, 27, 789.
54. Wolinski, K., Hinton, J. F., Pulay, P., J Am Chem Soc 1990, 112, 8251.
55. Biegler König, F. W., Schönbohm, J., Bayles, D., J Comput Chem 2001, 22, 545.
56. Bader, R. F. W., MacDougall, P. J., Lau, C. D. H., J Am Chem Soc 1984, 106, 1594.
57. Bader, R. F. W., Chem Rev 1991, 91, 893.
58. Mó, O., Yáñez, M., Elguero, J., J Chem Phys 1992, 97, 6628.
59. Mó, O., Yáñez, M., Elguero, J., J Mol Struct 1994, 314, 73.
60. Espinosa, E., Molins, E., Lecomte, C., Chem Phys Lett 1998, 285, 170.
61. Grabowski, S. J., J Phys Chem A 2000, 104, 5551.
62. Grabowski, S. J., J Phys Chem A 2001, 105, 10739.
63. Galvez, O., Gomez, P. C., Pacios, L. F., Chem Phys Lett 2001, 337, 263.
64. Galvez, O., Gomez, P. C., Pacios, L. F., J Chem Phys 2001, 115, 11166.
65. Galvez, O., Gomez, P. C., Pacios, L. F., J Chem Phys 2003, 118, 4878.
66. Pacios, L. F., J Phys Chem A 2004, 108, 1177.