Substituent effects on Cl⋯N, S⋯N, and P⋯N noncovalent bonds

Journal of Physical Chemistry A

Volumn 116, Issue 13, 2012, Pages 3487-3497

  Adhikari, Upendra ^a   Scheiner, Steve ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBONDING ORBITAL; ELECTRON-ACCEPTOR; ELECTROSTATIC COMPONENTS; H-BONDS; INDUCTION ENERGY; LONE PAIR; LOWEST ENERGY STRUCTURE; NONCOVALENT BOND; SUBSTITUENT EFFECT; TRANSFER OF CHARGES;

BINDING ENERGY; NITROGEN OXIDES; QUANTUM CHEMISTRY;

ATOMS;

EID: 84859599070     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp301288e     Document Type: Article

References (89)

1. The Hydrogen Bond. Recent Developments in Theory and Experiments; Schuster, P., Zundel, G., Sandorfy, C., Eds.; North-Holland Publishing Co.: Amsterdam, The Netherlands, 1976.
2. Schuster, P. Hydrogen Bonds; Springer-Verlag: Berlin, Germany, 1984; Vol. 120.
3. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, Germany, 1991.
4. Scheiner, S. Hydrogen Bonding. A Theoretical Perspective; Oxford University Press: New York, 1997.
5. Gilli, G.; Gilli, P. The Nature of the Hydrogen Bond; Oxford University Press: Oxford, U.K., 2009.
6. Wieczorek, R.; Dannenberg, J. J. J. Am. Chem. Soc. 2003, 125, 8124-8129
7. Alabugin, I. V.; Manoharan, M.; Peabody, S.; Weinhold, F. J. Am. Chem. Soc. 2003, 125, 5973-5987
8. Hernández-Soto, H.; Weinhold, F.; Francisco, J. S. J. Chem. Phys. 2007, 127, 164102
9. Bene, J. E. D.; Alkorta, I.; Elguero, J. Phys. Chem. Chem. Phys. 2011, 13, 13951-13961
10. Thakur, T. S.; Kirchner, M. T.; Blaöser, D.; Boese, R.; Desiraju, G. R. Phys. Chem. Chem. Phys. 2011, 13, 14076-14091
11. McDowell, S. A. C.; Buckingham, A. D. Phys. Chem. Chem. Phys. 2011, 13, 14097-14100
12. Gu, Y.; Kar, T.; Scheiner, S. J. Mol. Struct. 2000, 552, 17-31
13. Hydrogen Bonding - New Insights; Grabowski, S. J., Ed.; Springer: Dordrecht, The Netherlands, 2006.
14. Desiraju, G. R. Angew. Chem., Int. Ed. 2011, 50, 52-59
15. Arunan, E.; Desiraju, G. R.; Klein, R. A.; Sadlej, J.; Scheiner, S.; Alkorta, I.; Clary, D. C.; Crabtree, R. H.; Dannenberg, J. J.; Hobza, P. Pure Appl. Chem. 2011, 83, 1637-1641
16. Veken, B. J. v. D.; Delanoye, S. N.; Michielsen, B.; Herrebout, W. A. J. Mol. Struct. 2010, 976, 97-104
17. Takahashi, O.; Kohno, Y.; Nishio, M. Chem. Rev. 2010, 110, 6049-6076
18. Alkorta, I.; Elguero, J.; Bene, J. E. D. Chem. Phys. Lett. 2010, 489, 159-163
19. Rizzato, S.; Bergès, J.; Mason, S. A.; Albinati, A.; Kozelka, J. Angew. Chem., Int. Ed. 2010, 49, 7440-7443
20. Lommerse, J. P. M; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108-3116
21. Alkorta, I.; Rozas, S.; Elguero, J. J. Phys. Chem. A 1998, 102, 9278-9285
22. Wash, P. L.; Ma, S.; Obst, U.; Rebek, J. J. Am. Chem. Soc. 1999, 121, 7973-7974
23. Nguyen, H. L.; Horton, P. N.; Hursthouse, M. B.; Legon, A. C.; Bruce, D. W. J. Am. Chem. Soc. 2004, 126, 16-17
24. Cavallo, G.; Metrangolo, P.; Pilati, T.; Resnati, G.; Sansotera, M.; Terraneo, G. Chem. Soc. Rev. 2010, 39, 3772-3783
25. Politzer, P.; Murray, J. S.; Clark, T. Phys. Chem. Chem. Phys. 2010, 12, 7748-7757
26. Chudzinski, M. G.; McClary, C. A.; Taylor, M. S. J. Am. Chem. Soc. 2011, 133, 10559-10567
27. Zierkiewicz, W.; Wieczorek, R.; Hobza, P.; Michalska, D. Phys. Chem. Chem. Phys. 2011, 13, 5105-5113
28. Walter, S. M.; Kniep, F.; Herdtweck, E.; Huber, S. M. Angew. Chem., Int. Ed. 2011, 50, 7187-7191
29. Scheiner, S. Phys. Chem. Chem. Phys. 2011, 13, 13860-13872
30. Solimannejad, M.; Gharabaghi, M.; Scheiner, S. J. Chem. Phys. 2011, 134, 024312
31. Scheiner, S. J. Chem. Phys. 2011, 134, 094315
32. Scheiner, S. J. Phys. Chem. A 2011, 115, 11202-11209
33. Scheiner, S. Chem. Phys. Lett. 2011, 514, 32-35
34. Scheiner, S. Chem. Phys. 2011, 387, 79-84
35. Scheiner, S.; Adhikari, U. J. Phys. Chem. A 2011, 115, 11101-11110
36. Adhikari, U.; Scheiner, S. J. Chem. Phys. 2011, 135, 184306
37. Muller, G.; Brand, J.; Jetter, S. E. Z. Naturforsch., B: Chem. Sci 2001, 56, 1163-1171
38. Bushuk, S. B.; Carre, F. H.; Guy, D. M. H.; Douglas, W. E.; Kalvinkovskya, Y. A.; Klapshina, L. G.; Rubinov, A. N.; Stupak, A. P.; Bushuk, B. A. Polyhedron 2004, 23, 2615-2623
39. Tschirschwitz, S.; Loönnecke, P.; Hey-Hawkins, E. Dalton Trans. 2007, 2007, 1377-1382
40. Kilian, P.; Slawin, A. M. Z.; Woollins, J. D. Chem. - Eur. J. 2003, 9, 215-222
41. Sundberg, M. R.; Uggla, R.; Viñas, C.; Teixidor, F.; Paavola, S.; Kivekaös, R. Inorg. Chem. Commun. 2007, 10, 713-716
42. Widhalm, M.; Kratky, C. Chem. Ber. 1992, 125, 679-689
43. Dalinger, I. L.; Vinogradov, V. M.; Shevelev, S. A.; Kuzmin, V. S. Mendeleev Commun. 1996, 6, 13-15
44. Butcher, R. J.; Gilardi, R.; Baum, K.; Trivedi, N. J. Thermochim. Acta 2002, 384, 219-227
45. Bernhardt, P. V.; Lawrance, G. A.; Hambley, T. W. Inorg. Chem. 1992, 31, 631-634
46. Scheiner, S. J. Chem. Phys. 2011, 134, 164313
47. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09, revision B.01 ed.; Gaussian, Inc: Wallingford, CT, 2009.
48. Hermida-Ramón, J. M.; Cabaleiro-Lago, E. M.; Rodríguez- Otero, J. J. Chem. Phys. 2005, 122, 204315
49. Riley, K. E.; Opt Holt, B. T.; Merz, K. M. J. J. Chem. Theory Comput. 2007, 3, 407-433
50. Lu, Y.-X.; Zou, J.-W.; Fan, J.-C.; Zhao, W.-N.; Jiang, Y.-J.; Yu, Q.-S. J. Comput. Chem. 2008, 30, 725-732
51. Hyla-Kryspin, I.; Haufe, G.; Grimme, S. Chem. Phys. 2008, 346, 224-236
52. Biswal, H. S.; Wategaonkar, S. J. Phys. Chem. A 2009, 113, 12774-12782
53. Osuna, R. M.; Hernández, V.; Navarrete, J. T. L.; DOria, E.; Novoa, J. J. Theor. Chem. Acc. 2011, 128, 541-553
54. Zeng, Y.; Zhang, X.; Li, X.; Zheng, S.; Meng, L. Int. J. Quantum Chem. 2011, 111, 3725-3740
55. Wu, J. Int. J. Quantum Chem. 2011, 111, 4247-4254
56. Zhao, Q.; Feng, D.; Sun, Y.; Hao, J.; Cai, Z. Int. J. Quantum Chem. 2011, 111, 3881-3887
57. Hauchecorne, D.; Moiana, A.; Veken, B. J. v. d.; Herrebout, W. A. Phys. Chem. Chem. Phys. 2011, 13, 10204-10213
58. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566
59. Junming, L.; Yunxiang, L.; Subin, Y.; Weiliang, Z. Struct. Chem. 2011, 22, 757-763
60. Riley, K. E.; Murray, J. S.; Fanfrlík, J.; Rezác, J.; Solá, R. J.; Concha, M. C.; Ramos, F. M.; Politzer, P. J. Mol. Model. 2011, 17, 3309-3318
61. Li, Q.; Li, R.; Yi, S.; Li, W.; Cheng, J. Struct. Chem. 2012, 23, 411-416
62. Lu, Y.; Li, H.; Zhu, X.; Liu, H.; Zhu, W. Int. J. Quantum Chem. 2012, 112, 1421-1430
63. Wang, Z.; Liu, Z.; Ding, X.; Yu, X.; Hou, B.; Yi, P. Comput. Theor. Chem. 2012, 981, 1-6
64. Tsuzuki, S.; Wakisaka, A.; Ono, T.; Sonoda, T. Chem. - Eur. J. 2012, 18, 951-960
65. Zahn, S.; Frank, R.; Hey-Hawkins, E.; Kirchner, B. Chem. - Eur. J. 2011, 17, 6034-6038
66. Feng, G.; Evangelisti, L.; Gasparini, N.; Caminati, W. Chem. - Eur. J. 2012, 18, 1364-1368
67. Karthikeyan, S.; Sedlak, R.; Hobza, P. J. Phys. Chem. A 2011, 115, 9422-9428
68. Munusamy, E.; Sedlak, R.; Hobza, P. ChemPhysChem 2011, 12, 3253-3261
69. Zierkiewicz, W.; Czarnik-Matusewicz, B.; Michalska, D. J. Phys. Chem. A 2011, 115, 11362-11368
70. Grabowski, S. J. J. Phys. Chem. A 2012, 116, 1838-1845
71. Szostak, R. Chem. Phys. Lett. 2011, 516, 166-170
72. Lu, X.; Shi, H.; Chen, J.; Ji, D. Comput. Theor. Chem. 2012, 982, 34-39
73. Reed, A. E.; Weinhold, F.; Curtiss, L. A.; Pochatko, D. J. J. Chem. Phys. 1986, 84, 5687-5705
74. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926
75. Szalewicz, K.; Jeziorski, B.. Symmetry-adapted perturbation theory of intermolecular interactions. In Molecular Interactions. From Van der Waals to Strongly Bound Complexes; Scheiner, S., Ed.; Wiley: New York, 1997; pp 3-43.
76. Moszynski, R.; Wormer, P. E. S.; Jeziorski, B.; van der Avoird, A. J. Chem. Phys. 1995, 103, 8058-8074
77. Werner, H.-J.; Knowles, P. J.; Manby, F. R.; M. Schuötz; Celani, P.; Knizia, G.; Korona, T.; Lindh, R.; Mitrushenkov, A.; Rauhut, G.; MOLPRO, version 2006 ed.; University College Cardiff Consultants Limited: Cardiff, Wales, U.K., 2010.
78. Cybulski, S. M.; Scheiner, S. Chem. Phys. Lett. 1990, 166, 57-64
79. Murray, J. S.; Concha, M. C.; Lane, P.; Hobza, P.; Politzer, P. J. Mol. Model. 2008, 14, 699-704
80. Murray, J. S.; Lane, P.; Politzer, P. Int. J. Quantum Chem. 2008, 108, 2770-2781
81. Murray, J. S.; Lane, P.; Clark, T.; Riley, K. E.; Politzer, P. J. Mol. Model. 2012, 18, 541-548
82. Adhikari, U.; Scheiner, S. Chem. Phys. Lett. 2011, 514, 36-39
83. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
84. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
85. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824
86. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865-3868
87. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
88. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 1009-1018
89. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2007, 3, 289-300