Interaction of 1,2,5-chalcogenadiazole derivatives with thiophenolate: Hypercoordination with formation of interchalcogen bond versus reduction to radical anion

Journal of Physical Chemistry A

Volumn 115, Issue 18, 2011, Pages 4851-4860

  Suturina, Elizaveta A ^a,b   Semenov, Nikolay A ^c   Lonchakov, Anton V ^a,b   Bagryanskaya, Irina Yu ^c   Gatilov, Yuri V ^c   Irtegova, Irina G ^c   Vasilieva, Nadezhda V ^c   Lork, Enno ^d   Mews, Rüdiger ^d   Gritsan, Nina P ^a,b   Zibarev, Andrey V ^b,c  

^a INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

^c N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^d UNIVERSITY OF BREMEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

18-CROWN-6; 5]THIADIAZOLE; COVALENT RADII; DFT CALCULATION; DONOR-ACCEPTORS; HETEROCYCLES; HYPERCOORDINATION; NBO ANALYSIS; NEGATIVE CHARGE; POSITIVE ELECTRON AFFINITIES; RADICAL ANIONS; REACTION SYSTEM; THERMALLY STABLE; THERMODYNAMICS AND KINETICS; VAN DER WAALS RADIUS; X-RAY STRUCTURE;

CROWN ETHERS; ELECTRON AFFINITY; ORGANIC COMPOUNDS; REACTION KINETICS; THERMODYNAMICS; VAN DER WAALS FORCES;

NEGATIVE IONS;

ANION; FREE RADICAL; PYRROLE DERIVATIVE; SELENIUM DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; QUANTUM THEORY; THERMODYNAMICS;

ANIONS; AZOLES; FREE RADICALS; KINETICS; MOLECULAR STRUCTURE; QUANTUM THEORY; SELENIUM COMPOUNDS; SULFHYDRYL COMPOUNDS; THERMODYNAMICS;

EID: 79955788099     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp2019523     Document Type: Article

References (154)

1. Todres, Z. V. Ion-Radical Organic Chemistry: Principles and Applications; CRC Press/Taylor & Francis: Boca Raton, 2009.
2. Denning, M. S.; Irwin, M.; M. Golcoechea, M. Inorg. Chem. 2008, 47, 6118-6120
3. Gallardo, I.; Guirado, G.; Marquet, J.; Vila, N. Angew. Chem., Int. Ed. 2007, 46, 1321-1325
4. Rusakov, A. I.; Mendkovich, A. S.; Gultai, V. P.; Orlov, V. Yu. Structure and Reactivity of Organic Radical Anions; Mir Publishers: Moscow, 2005, (in Russian).
5. Todres, Z. V. Organic Ion Radicals; CRC Press: Boca Raton, 2002.
6. Boere, R. T.; Roemmele, T. L. Coord. Chem. Rev. 2000, 210, 369-445
7. Saito, G.; Yoshida, Y. Bull. Chem. Soc. Jpn. 2007, 80, 1-137
8. Yagubskii, E. B. In Organic Conductors, Superconductor, and Magnets: From Synthesis to Molecular Electronics; Ouahab, L.; Yagubskii, E., Eds.; Kluwer: Dordrecht, 2004.
9. Motokawa, N.; Miyasaka, H.; Yamashita, M.; Dunbar, K. R. Angew. Chem., Int. Ed. 2008, 47, 7760-7763
10. Yamashida, Y.; Tomura, T. J. Mater. Chem. 1998, 8, 1933-1944
11. Tsubata, Y.; Suzuki, T.; Yamashita, Y.; Mikai, T.; Miyashi, T. Heterocycles 1992, 33, 337-348
12. Yamashita, Y.; Mikai, T.; Miyashi, T.; Saito, G. Bull. Chem. Soc. Jpn. 1988, 61, 483-493
13. Choua, S.; Djukic, J. P.; Dallery, J.; Bieber, A.; Welter, R.; Gisselbrecht, J. P.; Turek, P.; Ricard, L. Inorg. Chem. 2009, 48, 149-163
14. Gloekle, M.; Hueber, K.; Kuemmerer, H. J.; Denninger, G.; Kaim, W. Inorg. Chem. 2001, 40, 2263-2269
15. Schwach, M.; Hausen, H. D.; Kaim, W. Inorg. Chem. 1999, 38, 2242-2243
16. Bock, H.; John, A.; Naether, C.; Ruppert, K. Helv. Chim. Acta 1994, 77, 1505-1509
17. Miller, J. S. J. Mater. Chem. 2010, 20, 1846-1857
18. Her, J. H.; Stephens, P. W.; Ribas-Arino, J.; Novoa, J. J.; Shum, W. W.; Miller, J. S. Inorg. Chem. 2009, 48, 3296-3307
19. Miller, J. S. Polyhedron 2009, 28, 1596-1605
20. Miller, J. S. Dalton Trans. 2006, 2742-2749
21. Miller, J. S. Inorg. Chem. 2000, 39, 4392-4408
22. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. 1994, 33, 385-415
23. Miller, J. S.; Epstein, A. J.; Reiff, W. M. Chem. Rev. 1988, 88, 201-220
24. Koizumi, K.; Shoji, M.; Ritawaga, Y.; Takeda, R.; Yamanaka, S.; Kawakami, T.; Okumura, M.; Yamaguchi, K. Polyhedron 2007, 26, 2135-2141
25. Broderick, W. E.; Eichhorn, D. M.; Liu, X.; Toscano, P. J.; Owens, S. M.; Hoffman, B. M. J. Am. Chem. Soc. 1995, 117, 3641-3642
26. Eichhorn, D. M.; Skee, D. C.; Broderick, W. E.; Hoffman, B. M. Inorg. Chem. 1993, 32, 491-492
27. Broderick, W. E.; Hoffman, B. M. J. Am. Chem. Soc. 1991, 113, 6334-6335
28. Brandon, R. L.; Osiecki, J. H.; Ottenberg, A. J. Org. Chem. 1966, 31, 1214-1217
29. Lu, J. M.; Rosokha, S. V.; Neretin, I. S.; Kochi, J. K. J. Am. Chem. Soc. 2006, 128, 16708-16719
30. Bencini, A.; Daul, C. A.; Dei, A.; Mariotti, F.; Lee, H.; Shulz, D. A.; Sorace, L. Inorg. Chem. 2001, 40, 1582-1590
31. Shulz, D. A.; Bodnar, S. H.; Vostrikova, K. E.; Kampf, J. W. Inorg. Chem. 2000, 39, 6091-6093
32. Pierpoint, C. G.; Lange, C. W. Prog. Inorg. Chem. 1994, 41, 331-442
33. Adams, M.; Dei, A.; Rheingold, A. L.; Hendrickson, D. N. Angew. Chem., Int. Ed. 1993, 32, 880-882
34. Dei, A.; Gatteschi, D. Inorg. Chim. Acta 1992, 198-200, 813-822
35. Chivers, T.; Laitinen, R. S. In Handbook of Chalcogen Chemistry. New Perspectives in Sulfur, Selenium and Tellurium; Devillanova, F., Ed.; RSC Press: Cambridge, U.K., 2007.
36. Chivers, T. A Guide to Chalcogen-Nitrogen Chemistry; World Scientific: Singapore, 2005.
37. Koutentis, P. A. Comprehensive Heterocyclic Chemistry III; Pergamon Press: Oxford, 2008; Vol. 5.
38. Yamazaki, R. Comprehensive Heterocyclic Chemistry III; Pergamon Press: Oxford, 2008; Vol. 6.
39. Koutentis, P. A. Sci. Synth. 2004, 13, 297-348
40. Aitken, R. A. Sci. Synth. 2004, 13, 777-822
41. Grivas, S. Curr. Org. Chem. 2000, 4, 707-726
42. Shinkai, I.; Reider, P. In Comprehensive Heterocyclic Chemistry II; Pergamon Press: Oxford, 1996; Vol. 4.
43. Ulrich, H. Methoden der Organischen Chemie (Houben-Weyl); Thieme: Stuttgart, 1994; Vol. E8d.
44. Weinstock, L. M.; Shinkai, I. Comprehensive Heterocyclic Chemistry I; Pergamon Press: Oxford, 1984; Vol. 6.
45. During the two past decades, numerous chalcogen-nitrogen π-heterocyclic neutral radicals and radical cations were isolated and successfully used as building blocks in the design and synthesis of molecular magnets and conductors. Heavier chalcogen derivatives display enhanced conductivity and larger magnetic exchange interactions. Relevant literature is too abundant to be cited completely. For selected recent work, see: Hicks, R. G. In Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds; Hicks, R. G., Ed.; Wiley: New York, 2010; pp 317-380.
46. Clarke, C. S.; Jornet-Somoza, J.; Mota, F.; Novoa, J. J.; Deumal, M. J. Am. Chem. Soc. 2010, 132, 17817-17830
47. Lekin, K.; Winter, S. M.; Downie, L. E.; Bao, X.; Tse, J. S.; Desgreniers, S.; Secco, R. A.; Dube, P. A.; Oakley, R. T. J. Am. Chem. Soc. 2010, 132, 16212-16224
48. Tse, J. S.; Leitch, A. A.; Yu, X.; Bao, X.; Zhang, S.; Liu, Q.; Jin, C.; Secco, R. A.; Desgreniers, S.; Ohishi, Y; Oakley, R. T. J. Am. Chem. Soc. 2010, 132, 4876-4886
49. Cameron, T. S.; Decken, A.; Grein, F.; Knapp, C.; Passmore, J.; Rautiainen, J. M.; Shuvaev, K. V.; Thompson, R. C.; Wood, D. J. Inorg. Chem. 2010, 49, 7861-7879
50. Deumal, M.; Rawson, J. M.; Howard, J. A. K.; Copley, R. C. B.; Robb, M. A.; Novoa, J. J. Chem.-Eur. J. 2010, 16, 2741-2750
51. Mito, M.; Komorida, Y.; Tsuruda, H.; Tse, J. S.; Desgreniers, S.; Ohishi, Y.; Leitch, A. A.; Cvrkalj, K.; Robertson, C. M.; Oakley, R. T. J. Am. Chem. Soc. 2009, 131, 16012-16013
52. Leitch, A. A.; Yu., X.; Winter, S. M.; Secco, R. A.; Dube, P. A.; Oakley, R. T. J. Am. Chem. Soc. 2009, 131, 7112-7125
53. Robertson, R. C.; Leitch, A. A.; Cvrkalj, K.; Reed, R. W.; Myles, D. J. T.; Dube, P. A.; Oakley, R. T. J. Am. Chem. Soc. 2008, 130, 14791-14801
54. Robertson, R. C.; Leitch, A. A.; Cvrkalj, K.; Reed, R. W.; Myles, D. J. T.; Dube, P. A.; Oakley, R. T. J. Am. Chem. Soc. 2008, 130, 8414-8425
55. Shuvaev, K. V.; Decken, A.; Grein, F.; Abeldin, T. M. S.; Thompson, L. K.; Passmore, J. Dalton Trans. 2008, 4029-4037
56. Rawson, J. M.; Alberola, A. In Handbook of Chalcogen Chemistry. New Perspectives in Sulfur, Selenium and Tellurium; Devillanova, F., Ed.; RSC Press: Cambridge, U.K., 2007.
57. Robertson, C. M.; Myles, D. J. T.; Leitch, A. A.; Reed, R. W.; Dooley, B. M.; Frank, N. L.; Dube, P. A.; Thompson, L. K.; Oakley, R. T. J. Am. Chem. Soc. 2007, 129, 12688-12689
58. Saito, G.; Yoshida, Y. Bull. Chem. Soc. Jpn. 2007, 80, 1-137
59. Preuss, K. E. Dalton Trans. 2007, 2357-2369
60. Awaga, K.; Tanaka, T.; Shirai, T.; Umezono, Y.; Fujita, W. C. R. Chim. 2007, 10, 52-57
61. Leitch, A. A.; Brusso, J. L.; Cvrkalj, K.; Reed, R. W.; Robertson, C. M.; Dube, P. A.; Oakley, R. T. Chem. Commun. 2007, 3368-3370
62. Leitch, A. A.; Reed, R. W.; Robertson, C. M.; Britten, J. F.; Yu, X.; Secco, R. A.; Oakley, R. T. J. Am. Chem. Soc. 2007, 129, 7903-7914
63. Brusso, J. L.; Cvrkalj, K.; Leitch, A. A.; Oakley, R. T.; Reed, R. W.; Robertson, C. M. J. Am. Chem. Soc. 2006, 128, 15050-15081
64. Rawson, J. M.; Alberola, A.; Whalley, A. J. Mater. Chem. 2006, 16, 2560-2575
65. Cameron, T. S.; Decken, A.; Kowalczyk, R. M.; McInnes, E. J. L.; Passmore, J.; Rawson, J. M.; Shuvaev, K. V.; Thompson, L. K. Chem. Commun. 2006, 2277-2279
66. Decken, A.; Matar, S. M.; Passmore, J.; Shuvaev, K. V.; Thompson, L. K. Inorg. Chem. 2006, 45, 3878-3886
67. Cameron, T. S.; Lemaire, M. T.; Passmore, J.; Rawson, J. M.; Shuvaev, K. V.; Thompson, L. K. Inorg. Chem. 2005, 44, 2576-2578
68. Currently, main group chemistry and materials science dealing with heavier chalcogens attract much attention. Of special interest are the interchalcogen interactions. Despite relative weakness, these interactions, for example, Se⋯S, both intra- and intermolecular, primary and secondary, play a unique role in physical, chemical, and biological processes, including, in particular, transfer of chiral information in chemical reactions. For selected recent work, see: Gamez, G. A.; Yanez, M. Chem. Commun. 2011, DOI: 10.1039/C0CC04675B.
69. Makherjee, A. J.; Zade, S. S.; Singh, H. B.; Suno, R. B. Chem. Rev. 2010, 110, 4357-4416
70. In Handbook of Chalcogen Chemistry. New Perspectives in Sulfur, Selenium and Tellurium; Devillanova, F., Ed.; RSC Press: Cambridge, U.K., 2007.
71. Bleiholder, C.; Werz, D. B.; Koeppel, H.; Gleiter, R. J. Am. Chem. Soc. 2006, 128, 2666-2674
72. Roy, D.; Sunoj, R. B. J. Phys. Chem. A 2006, 110, 5942-5947
73. Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Santoro, S.; Marini, F.; Bagnoli, L.; Temperini, A.; Constantino, F. Eur. J. Org. Chem. 2006, 4867-4873
74. Bachrach, S. M.; Demoin, D. W.; Luk, M.; Miller, J. V. J. Phys. Chem. A 2004, 108, 4040-4046
75. Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Marini, F.; Bagnoli, L.; Temperini, A. Angew. Chem., Int. Ed. 2003, 42, 3131-3133
76. Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Marini, F.; Bagnoli, L.; Temperini, A. Chem.-Eur. J. 2002, 8, 1118-1124
77. Vargas-Baca, I.; Chivers, T. Phosphorus Sulfur Silicon Relat. Elem. 2000, 164, 207-227
78. Zibarev, A. V.; Mews, R. In Frontiers of Selenium and Tellurium Chemistry: From Small Molecules to Biomolecules and Materials; Laitinen, R. S.; Woollins, J. D., Eds.; Springer: New York, 2011; in press.
79. Vasilieva, N. V.; Irtegova, I. G.; Gritsan, N. P.; Lonchakov, A. V.; Makarov, A. Yu.; Shundrin, L. A.; Zibarev, A. V. J. Phys. Org. Chem. 2010, 23, 536-543
80. Gritsan, N. P.; Suturina, E. A.; Semenov, N. A.; Lonchakov, A. V.; Zibarev, A. V. Work in progress.
81. Hanson, P. Adv. Heterocycl. Chem. 1980, 27, 31-149
82. Kwan, C. L.; Carmack, M.; Kochi, J. K. J. Phys. Chem. 1976, 80, 1786-1792
83. Kamiya, M.; Akahori, Y. Bull. Chem. Soc. Jpn. 1970, 43, 268-271
84. Atherton, N. M.; Ockwell, J. N.; Dietz, R. J. Chem. Soc. A 1967, 771-777
85. Konchenko, S. N.; Gritsan, N. P.; Lonchakov, A. V.; Radius, U.; Zibarev, A. V. Mendeleev Commun. 2009, 19, 7-9
86. Semenov, N. A.; Pushkarevsky, N. A.; Lonchakov, A. V.; Bogomyakov, A. S.; Pritchina, E. A.; Suturina, E. A.; Gritsan, N. P.; Konchenko, S. N.; Mews, R.; Ovcharenko, V. I.; Zibarev, A. V. Inorg. Chem. 2010, 49, 7558-7564
87. Konchenko, S. N.; Gritsan, N. P.; Lonchakov, A. V.; Irtegova, I. G.; Mews, R.; Ovcharenko, V. I.; Radius, U.; Zibarev, A. V. Eur. J. Inorg. Chem. 2008, 3833-3838
88. Gritsan, N. P.; Lonchakov, A. V.; Lork, E.; Mews, R.; Pritchina, E. A.; Zibarev, A. V. Eur. J. Inorg. Chem. 2008, 1994-1998
89. Bagryanskaya, I. Yu.; Gatilov, Yu. V.; Gritsan, N. P.; Ikorskii, V. N.; Irtegova, I. G.; Lonchakov, A. V.; Lork, E.; Mews, R.; Ovcharenko, V. I.; Semenov, N. A.; Vasilieva, N. V.; Zibarev, A. V. Eur. J. Inorg. Chem. 2007, 4751-4761
90. Ikorskii, V. N.; Irtegova, I. G.; Lork, E.; Makarov, A. Yu.; Mews, R.; Ovcharenko, V. I.; Zibarev, A. V. Eur. J. Inorg. Chem. 2006, 3061-3067
91. Makarov, A.Yu.; Irtegova, I. G.; Vasilieva, N. V.; Bagryanskaya, I. Yu.; Borrmann, T.; Gatilov, Yu. V.; Lork, E.; Mews, R.; Stohrer, W.-D.; Zibarev, A. V. Inorg. Chem. 2005, 44, 7194-7199
92. Emge, T. J.; Romanelly, M. D.; Moore, B. F.; Brennan, J. G. Inorg. Chem. 2010, 49, 7304-7312
93. Fuller, A. L.; Knight, F. R.; Slawin, A. M. Z.; Woollins, J. D. Eur. J. Inorg. Chem. 2010, 4034-4043
94. Eichhoefer, A.; Wood, P. T.; Viswanath, R.; Mole, R. A. Eur. J. Inorg. Chem. 2007, 4794-4799
95. Gimeno, M. C. In Handbook of Chalcogen Chemistry. New Perspectives in Sulfur, Selenium and Tellurium; Devillanova, F., Ed.; RSC Press: Cambridge, U.K., 2007.
96. Sadekov, I. D.; Minkin, V. I. J. Sulfur Chem. 1997, 19, 285-348
97. Stuzhin, P. A.; Bauer, E. M.; Ercolani, C. Inorg. Chem. 1999, 37, 1533-1539
98. Bauer, E. M.; Ercolani, C.; Galli, P.; Popkova, I. A.; Stuzhin, P. A. J. Porphyrins Phthalocyanines 1999, 3, 371-379
99. Duling, D. R. J. Magn. Reson. 1994, 104, 105-110
100. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122
101. Spek, A. L. PLATON program, A Multipurpose Crystallographic Tool, version 1.15; Utrecht University: Utrecht, The Netherlands, 2008.
102. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-17
103. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
104. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
105. Blockhuys, F. In Computational Methods in Science and Engineering. Advances in Computational Science; Maroulis, G.; Simos, T. E., Eds.; American Institute of Physics: Woodbury, NY, 2009; Vol. 1.
106. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
107. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
108. Schafer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577
109. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297-3305
110. Weigend, F. Phys. Chem. Chem. Phys. 2006, 8, 1057-1065
111. Dreuw, A.; Head-Gordon, M. Chem. Rev. 2005, 105, 4009-4037
112. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2006, 110, 13126-13130
113. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
114. Frisch, M. J.; Gaussian 09, Revision A.1; Gaussian Inc.: Wallingford, CT, 2009, (full reference available in the Supporting Information).
115. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
116. Barove, V.; Polimeno, A. Chem. Soc. Rev. 2007, 36, 1724-1731
117. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396
118. Keith, T. A. AIMAll, Version 10.03.25; aim.tkgristll.com.
119. Lee, L. M.; Elder, P. J. W.; Cozzolino, A. F.; Yang, Q.; Vargas-Baca, I. Main Group Chem. 2010, 9, 117-133
120. Cozzolino, A. F.; Bain, A. D.; Hanhan, S.; Vargas-Baca, I. Chem. Commun. 2009, 4043-4045
121. Risto, M.; Reed, R. W.; Robertson, C. M.; Oilunkaniemi, R.; Laitinen, R. S.; Oakley, R. T. Chem. Commun. 2008, 3278-3280
122. Nunn, A. J.; Ralph, J. T. J. Chem. Soc. C 1966, 1568-1570
123. Lork, E.; Mews, R.; Zibarev, A. V. Mendeleev Commun. 2009, 19, 147-148
124. Cordero, B.; Gomez, V.; Platero-Prats, A. E.; Reves, M.; Echeverria, J.; Cremades, E.; Barragan, F.; Alvarez, S. Dalton Trans. 2008, 2832-2838
125. Rowland, R. S.; Taylor, R. J. Phys. Chem. 1996, 100, 7384-7391
126. Bondi, A. J. Phys. Chem. 1964, 68, 441-451
127. Kumar, S.; Panda, S.; Singh, H. B.; Woltmershaeuser, G.; Butcher, R. J. Struct. Chem. 2007, 18, 127-132
128. Mugesh, G.; du Mont, W.-W.; Wismach, C.; Jones, P. G. ChemBioChem 2002, 3, 440-447
129. Neugebauer, D.; Schubert, U. J. Organomet. Chem. 1983, 256, 43-46
130. Atanassov, P. K.; Linden, A.; Heimgartner, H. J. Sulfur Chem. 2006, 27, 181-191
131. Billing, D. G.; Levendis, D. C.; Reid, D. H. Acta Crystallogr. C 1991, 47, 759-761
132. Allen, C.; Boeyens, J. C. A.; Briggs, A. G.; Denner, L.; Markwell, A. J.; Reid, D. H.; Rose, B. G. Chem. Commun. 1987, 967-968
133. Chidambaram, S. P.; Aravamudan, G.; Seshasayee, M. Z. Kristallogr. 1989, 187, 231-233
134. Husebye, S.; Maartmann-Moe, K. Acta Chem. Scand. A 1983, 37, 219-225
135. Anderson, O. P.; Husebye, S. Acta Chem. Scand. 1970, 24, 3141-3150
136. Trofimov, B. A.; Sinegovskaya, L. M.; Gusarova, N. K. J. Sulfur Chem. 2009, 30, 518-554
137. Riley, K.; Pitonak, M.; Jurecka, P.; Hobza, P. Chem. Rev. 2010, 110, 5023-5053
138. Kannemann, F. O.; Becke, A. D. J. Chem. Theory Comput. 2010, 6, 1081-1088
139. Sherrill, C. D.; Takatani, T.; Hohenstein, E. G. J. Phys. Chem. A 2009, 113, 10146-10159
140. Johnson, E. R.; Mackie, I. D.; DiLabio, G. A. J. Phys. Org. Chem. 2009, 22, 1127-1135
141. Cozzolino, A. F.; Yang, Q.; Vargas-Baca, I. Cryst. Growth Des. 2010, 10, 4959-4964
142. 2-3,4-dicyano-1,2,5- telluradiazolide (X = Cl, Br) anions are prepared and characterized by XRD).
143. In The Quantum Theory of Atoms in Molecules; Motta, C. F.; Boid, R. J., Eds.; Wiley: Weinheim, 2007.
144. Bader, R. F. W. Monatsh. Chem. 2005, 136, 819-856
145. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, 1990.
146. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926
147. Weinhold, F.; Landis, C. R. Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: Cambridge, U.K., 2005.
148. Iwaoka, M.; Katsuda, T.; Kamatsu, H.; Tomada, S. J. Org. Chem. 2005, 70, 321-327
149. Iwaoka, M.; Komatsu, H.; Katsuda, T.; Tomada, S. J. Am. Chem. Soc. 2004, 126, 5309-5317
150. Besler, B. H.; Merz, K. M.; Kollmann, P. A. J. Comput. Chem. 1990, 11, 431-439
151. Singh, U. C.; Kollman, P. A. J. Comput. Chem. 1984, 5, 129-145
152. Barbara, P. F.; Meyer, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 13148-13168
153. In Electron Transfer in Inorganic, Organic, and Biological Systems; Bolton, J. R.; Mataga, N.; McLendon, G., Eds.; Advances in Chemistry Series; American Chemical Society: Washington DC, 1991.
154. Marcus, R. A. J. Chem. Phys. 1956, 24, 966-978