Electrophilic attack on sulfur-sulfur bonds: Coordination of lithium cations to sulfur-rich molecules studied by ab initio MO methods

Chemistry - A European Journal

Volumn 11, Issue 4, 2005, Pages 1281-1293

  Steudel, Yana ^a   Wong, Ming Wah ^b   Steudel, Ralf ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Ab initio calculations; Cluster compounds; Ion molecule reactions; Lithium; Sulfur ligands

Indexed keywords

BINDING ENERGY; CHARGE TRANSFER; CONFORMATIONS; ISOMERS; POSITIVE IONS; SULFUR;

CLOSED SHELL INTERACTIONS; COMPLEX FORMATIONS; ION-DIPOLE ATTRACTION; NEUTRAL LIGANDS;

CHEMICAL BONDS;

DIMETHYL SULFIDE; HETEROCYCLIC COMPOUND; HEXASULFUR; HYDROGEN SULFIDE; LIGAND; LITHIUM; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CATION TRANSPORT; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATION; DENSITY; DIPOLE; ELECTROCHEMICAL ANALYSIS; ENERGY TRANSFER; GAS ANALYSIS; ION TRANSPORT; ISOMERISM; MOLECULAR INTERACTION; MOLECULAR MODEL; MOLECULAR ORBITAL METHOD; MOLECULAR STABILITY; SEPARATION TECHNIQUE;

CATIONS; COMPUTER SIMULATION; LIGANDS; LITHIUM; MODELS, CHEMICAL; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; QUANTUM THEORY; SULFUR COMPOUNDS; THERMODYNAMICS;

EID: 14544290997     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400852     Document Type: Article

References (73)

1. M. Schröder, S-Donor-Ligands, in: Encyclopedia of Inorganic Chemistry, Vol. 7 (Ed.: B. R. King), 1985, 3577-3594; Transition Metal Sulfur Chemistry (Eds.: E. I. Stiefel, K. Matsumoto), ACS Symposium Series 1996, Vol. 653.
2. M. Schröder, S-Donor-Ligands, in: Encyclopedia of Inorganic Chemistry, Vol. 7 (Ed.: B. R. King), 1985, 3577-3594; Transition Metal Sulfur Chemistry (Eds.: E. I. Stiefel, K. Matsumoto), ACS Symposium Series 1996, Vol. 653.
3. N. Takeda, N. Tokitoh, R. Okazaki, Top. Curr. Chem. 2003, 231, 153-202; M. G. Kanatzidis, S.-P. Huang, Coord. Chem. Rev. 1994, 130, 509-621; M. Draganjac, A. Müller, E. Diemann, Adv. Inorg. Chem. 1987, 31, 89; T. B. Rauchfuss, Angew. Chem. 1985, 97, 745-760; Angew. Chem. Int. Ed. Engl. 1985, 24, 742.
4. N. Takeda, N. Tokitoh, R. Okazaki, Top. Curr. Chem. 2003, 231, 153-202; M. G. Kanatzidis, S.-P. Huang, Coord. Chem. Rev. 1994, 130, 509-621; M. Draganjac, A. Müller, E. Diemann, Adv. Inorg. Chem. 1987, 31, 89; T. B. Rauchfuss, Angew. Chem. 1985, 97, 745-760; Angew. Chem. Int. Ed. Engl. 1985, 24, 742.
5. N. Takeda, N. Tokitoh, R. Okazaki, Top. Curr. Chem. 2003, 231, 153-202; M. G. Kanatzidis, S.-P. Huang, Coord. Chem. Rev. 1994, 130, 509-621; M. Draganjac, A. Müller, E. Diemann, Adv. Inorg. Chem. 1987, 31, 89; T. B. Rauchfuss, Angew. Chem. 1985, 97, 745-760; Angew. Chem. Int. Ed. Engl. 1985, 24, 742.
6. N. Takeda, N. Tokitoh, R. Okazaki, Top. Curr. Chem. 2003, 231, 153-202; M. G. Kanatzidis, S.-P. Huang, Coord. Chem. Rev. 1994, 130, 509-621; M. Draganjac, A. Müller, E. Diemann, Adv. Inorg. Chem. 1987, 31, 89; T. B. Rauchfuss, Angew. Chem. 1985, 97, 745-760; Angew. Chem. Int. Ed. Engl. 1985, 24, 742.
7. N. Takeda, N. Tokitoh, R. Okazaki, Top. Curr. Chem. 2003, 231, 153-202; M. G. Kanatzidis, S.-P. Huang, Coord. Chem. Rev. 1994, 130, 509-621; M. Draganjac, A. Müller, E. Diemann, Adv. Inorg. Chem. 1987, 31, 89; T. B. Rauchfuss, Angew. Chem. 1985, 97, 745-760; Angew. Chem. Int. Ed. Engl. 1985, 24, 742.
8. R. Steudel, Angew. Chem. 1975, 87, 683-692; Angew. Chem. Int. Ed. Engl. 1975, 14, 655-664.
9. R. Steudel, Angew. Chem. 1975, 87, 683-692; Angew. Chem. Int. Ed. Engl. 1975, 14, 655-664.
10. For calculated and experimental electron density maps of molecules containing divalent sulfur atoms, see ref. [9] and A. S. Brown, V. H. Smith, J. Chem. Phys. 1993, 99, 1837-1843.
11. A. Yokozeki, S. H. Bauer, J. Phys. Chem. 1976, 80, 618-625.
12. W.-K. Li, S.-W. Chiu, Z.-X. Ma, C.-L. Liao, C. Y. Ng, J. Chem. Phys. 1993, 99, 8440-8444; see also: S.-Y. Chiang, C.-I. Ma, D.-J. Shr, J. Chem. Phys. 1999, 110, 9056-9063.
13. W.-K. Li, S.-W. Chiu, Z.-X. Ma, C.-L. Liao, C. Y. Ng, J. Chem. Phys. 1993, 99, 8440-8444; see also: S.-Y. Chiang, C.-I. Ma, D.-J. Shr, J. Chem. Phys. 1999, 110, 9056-9063.
14. J. Berkowitz, C. Lifshitz, J. Chem. Phys. 1968, 48, 4346-4350.
15. J. Steidel, J. Pickardt, R. Steudel, Z. Naturforsch. B 1978, 33, 1554-1555.
16. P. Coppens, Y. W. Yang, R. H. Blessing, W. F. Cooper, F. K. Larsen, J. Am. Chem. Soc. 1977, 99, 760-766.
17. R. Steudel, J. Steidel, F. Schuster, J. Pickardt, R. Reinhardt, Z. Naturforsch. B 1980, 35, 1378-1383.
18. I. Krossing, J. Passmore, Inorg. Chem. 2004, 43, 1000-1011; see also: J. Cioslowski, A. Szarecka, D. Moncrieff, Int. J. Quantum Chem. 2002, 90, 1049-1054.
19. I. Krossing, J. Passmore, Inorg. Chem. 2004, 43, 1000-1011; see also: J. Cioslowski, A. Szarecka, D. Moncrieff, Int. J. Quantum Chem. 2002, 90, 1049-1054.
20. H. W. Roesky, M. Thomas, J. Schimkowiak, P. G. Jones, W. Pinkert, G. M. Sheldrick, J. Chem. Soc. Chem. Commun. 1982, 895-896.
21. T. S. Cameron, A. Decken, I. Dionne, M. Fang, I. Krossing, J. Passmore, Chem. Eur. J. 2092, 8, 3386-31401.
22. A. Bacchi, W. Baratta, F. Calderazzo, F. Marchetti, G. Pelizzi, Inorg. Chem. 2002, 41, 3894-3900.
23. F. A. Cotton, E. V. Dikarev, M. A. Petrukhina, Angew. Chem. 2001, 113, 1569-1571; Angew. Chem. Int. Ed. 2001, 40, 1521-1523.
24. F. A. Cotton, E. V. Dikarev, M. A. Petrukhina, Angew. Chem. 2001, 113, 1569-1571; Angew. Chem. Int. Ed. 2001, 40, 1521-1523.
25. I. G. Dance, K. J. Fisher, G. D. Witt, Inorg. Chem. 1996, 35, 4177-4184; I. Dance, ACS Symp. Ser. 1996, 655, 135-152; K. Fisher, I. Dance, G. Willett, J. Chem. Soc. Dalton Trans. 1998, 975-980; P. Liu, C. Han, Z. Gao, F. Kong, Q. Zhu, J. Phys. Chem. B 1999, 103, 3337-3339.
26. I. G. Dance, K. J. Fisher, G. D. Witt, Inorg. Chem. 1996, 35, 4177-4184; I. Dance, ACS Symp. Ser. 1996, 655, 135-152; K. Fisher, I. Dance, G. Willett, J. Chem. Soc. Dalton Trans. 1998, 975-980; P. Liu, C. Han, Z. Gao, F. Kong, Q. Zhu, J. Phys. Chem. B 1999, 103, 3337-3339.
27. I. G. Dance, K. J. Fisher, G. D. Witt, Inorg. Chem. 1996, 35, 4177-4184; I. Dance, ACS Symp. Ser. 1996, 655, 135-152; K. Fisher, I. Dance, G. Willett, J. Chem. Soc. Dalton Trans. 1998, 975-980; P. Liu, C. Han, Z. Gao, F. Kong, Q. Zhu, J. Phys. Chem. B 1999, 103, 3337-3339.
28. I. G. Dance, K. J. Fisher, G. D. Witt, Inorg. Chem. 1996, 35, 4177-4184; I. Dance, ACS Symp. Ser. 1996, 655, 135-152; K. Fisher, I. Dance, G. Willett, J. Chem. Soc. Dalton Trans. 1998, 975-980; P. Liu, C. Han, Z. Gao, F. Kong, Q. Zhu, J. Phys. Chem. B 1999, 103, 3337-3339.
29. I. Dance, K. Fisher, G. Willett, Angew. Chem. 1995, 107, 215-218; Angew. Chem. Int. Ed. Engl. 1995, 34, 201-203; I. G. Dance, K.J. Fisher, G. D. Willett, J. Chem. Soc. Chem. Commun. 1995, 975.
30. I. Dance, K. Fisher, G. Willett, Angew. Chem. 1995, 107, 215-218; Angew. Chem. Int. Ed. Engl. 1995, 34, 201-203; I. G. Dance, K.J. Fisher, G. D. Willett, J. Chem. Soc. Chem. Commun. 1995, 975.
31. I. Dance, K. Fisher, G. Willett, Angew. Chem. 1995, 107, 215-218; Angew. Chem. Int. Ed. Engl. 1995, 34, 201-203; I. G. Dance, K.J. Fisher, G. D. Willett, J. Chem. Soc. Chem. Commun. 1995, 975.
32. A. M. El-Nahas, K. Hirao, J. Phys. Chem. A 2000, 104, 138-144; M. Remko, B. M. Rode, J. Mol. Struct. 2000, 505, 269-281.
33. A. M. El-Nahas, K. Hirao, J. Phys. Chem. A 2000, 104, 138-144; M. Remko, B. M. Rode, J. Mol. Struct. 2000, 505, 269-281.
34. M. Remko, B. M. Rode, J. Mol. Struct. 2000, 505, 269-281; M. Remko, M. Sarissky, Chem. Phys. Lett. 1998, 282, 227; M. Remko, K. R. Liedl, B. M. Rode, J. Phys. Chem. A 1998, 102, 771.
35. M. Remko, B. M. Rode, J. Mol. Struct. 2000, 505, 269-281; M. Remko, M. Sarissky, Chem. Phys. Lett. 1998, 282, 227; M. Remko, K. R. Liedl, B. M. Rode, J. Phys. Chem. A 1998, 102, 771.
36. M. Remko, B. M. Rode, J. Mol. Struct. 2000, 505, 269-281; M. Remko, M. Sarissky, Chem. Phys. Lett. 1998, 282, 227; M. Remko, K. R. Liedl, B. M. Rode, J. Phys. Chem. A 1998, 102, 771.
37. E. Magnusson, J. Phys. Chem. 1994, 98, 12558-12569.
38. R. Cimiraglia, J. Tomasi, R. Cammi, H. J. Hofmann, Chem. Phys. 1989, 756, 399-404.
39. B. Goldfuss, P. von R. Schleyer, F. Hampel, Organometallics 1997, 76, 5032-5041.
40. O. P. Charkin, M. L. McKee, N. M. Klimenko, P. von R. Schleyer, Zh. Neorg. Khim. 1998, 43, 294-302.
41. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, GAUSSIAN 98, Gaussian Inc., Pittsburgh, PA, 1998.
42. L. A. Curtiss, P. C. Redfern, K. Raghavachari, J. A. Pople, J. Chem. Phys. 2001, 114, 108-117.
43. L. A. Curtiss, P. C. Redfern, K. Raghavachari, V. Rassolov, J. A. Pople, J. Chem. Phys. 1999, 770, 4703-4709.
44. M. W. Wong, R. Steudel, Chem. Phys. Lett. 2003, 579, 162-169.
45. M. W. Wong, Y. Steudel, R. Steudel, Chem. Phys. Lett. 2092, 364, 387-392.
46. M. W. Wong, Y. Steudel, R. Steudel, J. Chem. Phys. 2004, 727, 5899-5907.
47. th Edition (Ed.: M.W. Chase), National Institute of Standards and Technology, New York, 1998.
48. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926.
49. M. Messerschmidt, A. Wagner, M. W. Wong, P. Luger, J. Am. Chem. Soc. 2002, 124, 732-733.
50. R. F. W. Bader, Atoms in Molecules - A Quantum Theory, Oxford University Press, Oxford, 1990.
51. A. H. Otto, R. Steudel, Z. Anorg. Allg. Chem. 2000, 626, 2063-2068.
52. F. Pauer, P. P. Power in Lithium Chemistry: A Theoretical and Experimental Overview (Eds.: A.-M. Sapse, P. von R. Schleyer) Wiley, New York, 1995, p. 295.
53. The same asymmetrical structure was obtained at the MP2/6311G(2df,p) level.
54. Q. Shen, C. Wells, K. Hagen, Inorg. Chem. 1998, 37, 3895-3898.
55. Y. Drozdova, K. Miaskiewicz, R. Steudel, Z. Naturforsch. B 1995, 50, 889-893.
56. R. Steudel, Chem. Rev. 2002, 102, 3905-3945.
57. M. W. Wong, T. S. Chwee, R. Steudel, J. Phys. Chem. A 2004, 108, 7091-7098.
58. J. Cioslowski, A. Szarecka, D. Moncrieff, J. Phys. Chem. A 2001, 105, 501-505.
59. M. D. Chen, M. L. Liu, H. B. Luo, Q. E. Zhang, C. T. Au, J. Mol. Struct. 2001, 548, 133-141.
60. S. Hunsicker, R. O. Jones, G. Ganteför, J. Chem. Phys. 1995, 702, 5917-5936.
61. R. Steudel, Y. Steudel, M. W. Wong, Top. Curr. Chem. 2002, 230, 117-134.
62. K. P. Huber, G. Herzberg, Constants of Diatomic Molecules, van - Nostrand Rheinhold, New York, 1979, p. 564.
63. D. Aris, J. Beck, A. Decken, I. Dionne, I. Krossing, J. Passmore, E. Rivard, F. Steden, X. Wang, Phosphorus Sulfur Silicon Relat. Elem. 2004, 179, 859-863.
64. M. C. McCarthy, S. Thorwirth, C. A. Gottlieb, P. Thaddeus, J. Am. Chem. Soc. 2004, 126, 4096-4097.
65. T. Mineva, N. Russo, E. Sicilia, M. Toscano, J. Chem. Soc. Faraday Trans. 1997, 93, 3309-3312.
66. R. Laitinen, R. Steudel, R. Weiss, J. Chem. Soc. Dalton Trans. 1986, 1095-1100.
67. F. M. Bickelhaupt, M. Sola, P. von R. Schleyer, J. Comput. Chem. 1995, 16, 465-477; R. Steudel, Y. Drozdova, K. Miaskiewicz, R. H. Hertwig, W. Koch, J. Am. Chem. Soc. 1997, 119, 1990-1996; P. Gerbaux, J.-Y. Salpin, G. Bouchoux, R. Flammang, Int. J. Mass Spectrom. 2000, 195/196, 239-249.
68. F. M. Bickelhaupt, M. Sola, P. von R. Schleyer, J. Comput. Chem. 1995, 16, 465-477; R. Steudel, Y. Drozdova, K. Miaskiewicz, R. H. Hertwig, W. Koch, J. Am. Chem. Soc. 1997, 119, 1990-1996; P. Gerbaux, J.-Y. Salpin, G. Bouchoux, R. Flammang, Int. J. Mass Spectrom. 2000, 195/196, 239-249.
69. F. M. Bickelhaupt, M. Sola, P. von R. Schleyer, J. Comput. Chem. 1995, 16, 465-477; R. Steudel, Y. Drozdova, K. Miaskiewicz, R. H. Hertwig, W. Koch, J. Am. Chem. Soc. 1997, 119, 1990-1996; P. Gerbaux, J.-Y. Salpin, G. Bouchoux, R. Flammang, Int. J. Mass Spectrom. 2000, 195/196, 239-249.
70. A. Vila, J. M. Pardo, R. A. Mosquera, Chem. Phys. Lett. 2003, 575, 499-505.
71. P. Burk, I. A. Koppel, I. Koppel, R. Kurg, J.-F. Gal, P.-C. Maria, M. Herreros, R. Notario, J.-L. M. Abboud, F. Anvia, R. W. Taft, J. Phys. Chem. A 2000, 104, 2824-2833; K. Tämm, D. C. Fara, A. R. Katritzky, P. Burk, M. Karelson, J. Phys. Chem. A 2004, 108, 4812-4818.
72. P. Burk, I. A. Koppel, I. Koppel, R. Kurg, J.-F. Gal, P.-C. Maria, M. Herreros, R. Notario, J.-L. M. Abboud, F. Anvia, R. W. Taft, J. Phys. Chem. A 2000, 104, 2824-2833; K. Tämm, D. C. Fara, A. R. Katritzky, P. Burk, M. Karelson, J. Phys. Chem. A 2004, 108, 4812-4818.
73. R. W. Taft, F. Anvia, J.-F. Gal, S. Walsh, M. Capon, M. C. Holmes, K. Hosn, G. Oloumi, R. Vasanwala, S. Yazdani, Pure Appl. Chem. 1990, 62, 17.