A combined experimental and theoretical electron density study of intra- and intermolecular interactions in thiourea S,S-dioxide

Chemistry - A European Journal

Volumn 9, Issue 13, 2003, Pages 3112-3121

  Lee, Chi Rung ^b   Tang, Ting Hua ^a   Chen, Likey ^a   Wang, Yu ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b MINGHSIN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

Author keywords

Charge density; Density functional calculations; Hydrogen bonds; Topological analysis; X ray diffraction

Indexed keywords

HYDROGEN BONDS; PROBABILITY DENSITY FUNCTION; UREA; X RAY DIFFRACTION ANALYSIS;

INTERMOLECULAR INTERACTIONS;

CARRIER CONCENTRATION;

AMPHOLYTE; THIOUREA DERIVATIVE;

ARTICLE; CHEMICAL BOND; CRYSTAL; DENSITY; DIPOLE; ELECTRON; HYDROGEN BOND; MOLECULAR INTERACTION; X RAY DIFFRACTION;

EID: 0041806722     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200204519     Document Type: Article

References (94)

1. a) C. F. Mellot, A. M. Davidson, J. Eckert, A. K. Cheethan, J. Phys. Chem. B 1998, 102, 2530-2535;
2. b) S. E. Barber, K. E. S. Dean, A. J. Kirby, Can. J. Chem. 1999, 77, 792-801;
3. c) C. Cox, T. Lectka, J. Am. Chem. Soc. 1998, 120, 10660-11668;
4. d) K.-J. Lin, Y. Wang, J. Phys. Chem. 1994, 98, 11685-11693;
5. e) A. Ivancich, T. A. Mattioli, Photosynth. Res. 1998, 55, 207-215;
6. f) A. Aurora, G. D. Rose, Protein Sci., 1998, 7, 21-38;
7. g) G. R. Desiraju, Crystal Engineering - The Design of Organic Solids, Elsevier, New York, 1989.
8. R. F. W. Bader, Atoms in Molecules: a Quantum Theory, Clarendon Press, Oxford, 1990.
9. M. T. Caroll, C. Chang, R. F. W. Bader, Mol. Phys. 1988, 63, 387-405.
10. M. T. Caroll, R. F. W. Bader, Mol. Phys. 1988, 65, 695-722.
11. P. L. A. Popelier, R. F. W. Bader, Chem. Phys. Lett. 1992, 189, 542-548.
12. T.-H. Tang, D. M. Whitefield, S. P. Douglas, J. J. Krepinsky, I. G. Csizmadia, Can. J. Chem. 1992, 70, 2434-2448.
13. D. M. Whitefield, T.-H. Tang, J. Am. Chem. Soc. 1993, 115, 9648-9654.
14. C. Gatti, V. R. Saunders, C. Roetti, J. Chem. Phys. 1994, 101, 10686-10696.
15. U. Koch, P. L. A. Popelier, J. Phys. Chem. 1995, 99, 9747-9754.
16. T.-H. Tang, Y.-P. Cui, Can. J. Chem. 1996, 74, 1162-1170.
17. J. A. Platts, S. T. Howard, J. Chem. Phys. 1996, 105, 4668-4674.
18. J. A. Platts, S. T. Howard, B. R. F. Bracke, J. Am. Chem. Soc. 1996, 118, 2726-2733.
19. P. L. A. Popelier, J. Phys. Chem. 1998, A102, 1873-1878.
20. C. Gatti, R. Bianchi, R. Destro, F. Merati, J. Mol. Struct.(THEOCHEM) 1992, 255, 409-433.
21. T. S. Koritsanszky, P. Coppens, Chem. Rev. 2001, 101, 1583-1627.
22. P. Coppens, X-ray Charge Densities and Chemical Bonding, Oxford University Press, Oxford, 1997.
23. P. Coppens, Acta Crystallogr. Sect. A 1998, 54, 779-788.
24. R. Flaig, T. Koritsgnszky, D. Zobel, P. Luger, J. Am. Chem. Soc. 1998, 120, 2227-2238.
25. E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett. 1998, 285, 170-173.
26. J. Overgaad, B. Schiøtt, F. K. Larsen, A. J. Schultz, J. C. MacDonald, B. B. Iversen, Angew. Chem. 1999, 111, 1321-1324; Angew. Chem. Int. Ed. 1999, 38, 1239-1242.
27. J. Overgaad, B. Schiøtt, F. K. Larsen, A. J. Schultz, J. C. MacDonald, B. B. Iversen, Angew. Chem. 1999, 111, 1321-1324; Angew. Chem. Int. Ed. 1999, 38, 1239-1242.
28. P. Coppens, Y. A. Abramov, M. Carducci, B. Korjov, I. Novozhilova, C. Alhambra, M. R. Pressprich, J. Am. Chem. Soc. 1999, 121, 2585-2593.
29. R. Flaig, T. Koritsánszky, J. Janczak, H.-G. Krane, W. Morgenroth, P. Luger, Angew. Chem. 1999, 111, 1494-1497; Angew. Chem. Int. Ed. 1999, 38, 1397-1400.
30. R. Flaig, T. Koritsánszky, J. Janczak, H.-G. Krane, W. Morgenroth, P. Luger, Angew. Chem. 1999, 111, 1494-1497; Angew. Chem. Int. Ed. 1999, 38, 1397-1400.
31. F. Benabicha, V. Pichon-Pesme, C. Jelsch, C. Lecomte, A. Khmou, Acta Crystallogr. Sect. B 2000, 56, 155-165.
32. W. D. Arnold, L. K. Sanders, M. T. McMahon, A. V. Volkov, G. Wu, P. Coppens, S. R. Wilson, N. Godbout, R. Oldfield, J. Am. Chem. Soc. 2000, 122, 4708-4717.
33. H.-P. Weber, B. M. Craven, Acta Crystallogr. Sect. B 1987, 43, 202-209.
34. R. F. W. Bader, Chem. Rev. 1991, 91, 893-928.
35. E. Kraka, D. Cremer in The Concept of the Chemical Bond, Theoretical Models of Chemical Bonding, Part 2 (Ed.: Z. B. Makic), Springer-Verlag, New York, 1990.
36. R. F. W. Bader, J. Phys. Chem. 1998, A102, 7314-7323.
37. C.-R. Lee, T.-H. Tang, C.-C. Wang, L. Chen, Y. Wang, unpublished results.
38. C.-R. Lee, L. Y. Tan, Y. Wang, J. Phys. Chem. of Solids, 2001, 62, 1613-1628.
39. C.-C. Wang, T.-H. Tang, Y. Wang, J. Phys. Chem. 2000, A104, 9566-9572.
40. C.-R. Lee, C.-C. Wang, K.-C. Chen, G.-H. Lee, Y. Wang, J. Phys. Chem. 1999, A103, 156-165.
41. V. G. Tsirelson, P.-F. Zou, T.-H. Tang, R. F. W. Bader, Acta Crystallogr. Sect. A 1995, 51, 143-153.
42. T.-H. Tang, R. F. W. Bader, P. J. MacDougall, Inorg. Chem. 1985, 24, 2047-2053.
43. W. Scherer, M. Spiegler, B. Pedersen, M. Tafiposky, W. Hieringer, B. Reinhard, A. J. Downs, G. S. McGrady, Chem. Commun. 2000, 635.
44. R. G. A. Bone, R. F. W. Bader, J. Phys. Chem. 1996, 100, 10892-10911.
45. a) Y. Aray, R. F. W. Bader, Surf. Sci. 1996, 351, 233-249;
46. b) Y. Aray, J. Rodriguez, D. Vega, J. Phys. Chem. 2000, B104, 5225-5231.
47. A. Gobbi, G. Frenking, J. Am. Chem. Soc. 1993, 115, 2362-2372.
48. A. Masunov, J. J. Dannenberg, J. Phys. Chem. 1999, A103, 178-184; A. Masunov, J. J. Dannenberg, J. Phys. Chem. 2000, B104, 806-810.
49. A. Masunov, J. J. Dannenberg, J. Phys. Chem. 1999, A103, 178-184; A. Masunov, J. J. Dannenberg, J. Phys. Chem. 2000, B104, 806-810.
50. R. Dovesi, M. Causá, R. Orlando, C. Roetti, V. R. Saunders, J. Chem. Phys. 1990, 92, 7402-7411.
51. S. Swaminathan, B. M. Craven, R. K. McMullan, Acta. Crystallogr. Sect. B 1984, 40, 300-306.
52. K. Suzuki, S. Onishi, T. Koide, S. Seki, Bull. Chem. Soc. Jpn. 1956, 29, 127-131.
53. a) V. Zavodnik, A. Stash, V. Tsirelson, R. de Vries, D. Feil, Acta Crystallogr. Sect. B 1999, 55, 45-54;
54. b) K. Y. Suponitsky, V. G. Tsirelson, D. Feil, Acta Crystallogr. Sect. A 1999, 55, 821-827;
55. c) R. Y. de Vries, D. Feil, V. G. Tsirelson, Acta Crystallogr. Sect. B 2000, 56, 118-123.
56. H. G. M. De Wit, J. C. Van Miltenburg, C. G. De Kruif, J. Thermodyn. 1983, 15, 651-654.
57. I.-C. Chen, Y. Wang, Acta Crystallogr. Sect. C 1984, 40, 1937-1938.
58. Y. Wang, N.-L. Chang, C.-T. Pai, Inorg. Chem. 1990, 29, 3256-3259.
59. A. Volkov, C. Gatti, Y. Abramov, P. Coppens, Acta Crystallogr. Sect. A 2000, 56, 252-258.
60. T.-S. Hwang, Y. Wang, J. Phys. Chem. 1998, A102, 3726-3731.
61. J. Cioslowski, P. R. Surján, J. Mol. Struct. (THEOCHEM) 1992, 255, 9-33.
62. A. E. Reed, P. v. R. Schleyer, J. Am. Chem. Soc. 1990, 112, 1434-1445.
63. J. A. Dobado, H. Martinez-Garcia, J. M. Molina, M. R. Sundberg, J. Am. Chem. Soc. 1998, 120, 8461-8471; J. A. Dobado, H. Martinez-Garcia, J. M. Molina, M. R. Sundberg, J. Am. Chem. Soc. 1999, 121, 3156-3164.
64. J. A. Dobado, H. Martinez-Garcia, J. M. Molina, M. R. Sundberg, J. Am. Chem. Soc. 1998, 120, 8461-8471; J. A. Dobado, H. Martinez-Garcia, J. M. Molina, M. R. Sundberg, J. Am. Chem. Soc. 1999, 121, 3156-3164.
65. A. Volkov, Y. Abramov, P. Coppens, C. Gatti, Acta Crystallogr. Sect. A 2000, 56, 332-339.
66. E. Espinosa, C. Lecomte, E. Molins, Chem. Phys. Lett. 1999, 300, 745-748.
67. Y. A. Abramov, Acta Crystallogr. Sect. A 1997, 53, 264-272.
68. E. Espinosa, I. Alkorta, I. Rozas, J. Elguero, E. Molins, Chem. Phys. Lett. 2001, 336, 457-461.
69. S. T. Howard, M. B. Hursthouse, C. W. Lehmann, P. R. Mallinson, C. S. Frampton, J. Chem. Phys. 1992, 97, 5616-5630.
70. Y. A. Abramov, A. V. Volkov, P. Coppens, Chem. Phys. Lett. 1999, 311, 81-86.
71. T. Koritsánszky, S. Howard, T. Richter, Z. Su, P. R. Mallinson, N. K. Hansen, XD (Computer Program Package for Multipole Refinement and Analysis of Electron Densities from X-ray Diffraction Data), Free University of Berlin, Germany, 1996.
72. N. H. Hansen, P. Coppens, Acta Crystallogr. Sect. A 1978, 34, 909-921.
73. N-H bond length ≈ 1.03 Å; see: F. H. Allen, Acta Crystallogr. Sect. B 1986, 42, 515-522.
74. M. Souhassou, R. H. Blessing, J. Appl. Crystallogr. 1999, 32, 210-217.
75. a) P. Hohenberg, W. Kohn, Phys. Rev. 1964, 136(B), B864-871;
76. b) W. Kohn, S. J. Sham, Phys. Rev. 1965,140(A), A1133-1138;
77. c) R. G. Parr, W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, 1989.
78. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, 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, 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. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98 (Revision A.7), Gaussian Inc., Pittsburgh, PA, 1998.
79. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B. 1988, 37(2), 785-789.
80. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
81. M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees, J. A. Pople, J. Chem. Phys. 1982, 77, 3654-3665.
82. V. R. Saunders, R. Dovesi, C. Roetti, M. Causá, N. M. Harrison, R. Orlando, C. M. Zicovich-Wilson, CRYSTAL 98 User's Manual, University of Torino, Italy, 1998.
83. R. F. W. Bader, F. W. Biegler-König, J. R. Cheeseman, J. A. Duke, T. A. Keith, P. Krug, K. E. Laidig, B. Langdon, AIMPAC (a set of programs for the theory of atoms in molecules), McMaster University, Hamilton, ON, Canada, 1994.
84. D.-C. Fang, T.-H. Tang, AIM98PC (modified PC version of AIMPAC), 1998.
85. C. Gatti, TOPOND98 User's Manual 1998, CNR-CSRSRC, Milano, Italy.
86. R. F. W. Bader, T.-H. Tang, Y. Tal, F. W. Biegler-König, J. Am. Chem. Soc. 1982, 104, 946-952.
87. a) R. F. W. Bader, T. Slee, D. Cremer, E. Kraka, J. Am. Chem. Soc. 1983, 105, 5061-5068;
88. b) S. M. Bachrach, J. Comput. Chem. 1989, 10, 392-406;
89. c) S. M. Bachrach, J. Mol. Struct. (THEOCHEM) 1992, 255, 207-219;
90. d) S. M. Bachrach, J. Mol. Struct. (THEOCHEM) 1995, 337, 201-207.
91. D. Cremer, E. Kraka, Croatica Chem. Acta 1984, 57, 1259-1281.
92. S. Grimme, J. Am. Chem. Soc. 1996, 118, 1529-1534.
93. F. W. Biegler-König, R. F. W. Bader, T.-H. Tang, J. Comp. Chem. 1982, 3, 317-328.
94. R. F. W. Bader, P. L. A. Popelier, C. Chang, J. Mol. Struct. (THEOCHEM) 1992, 255, 145-17.