Binding energies of organic charge-transfer complexes calculated by first-principles methods

Collection of Czechoslovak Chemical Communications

Volumn 63, Issue 8, 1998, Pages 1223-1244

  Rauwolf, Cordula ^a   Mehlhorn, Achim ^a   Fabian, Jürgen ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Ab initio calculations; Acceptor compounds; Charge transfer complexes; Density functional theory; Donor compounds; Donor acceptor interaction; Face to face stacking; Quantum chemistry; Self consistent reaction field; Solvent effect

Indexed keywords

EID: 84962420711     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc19981223     Document Type: Article

References (89)

1. a) Hobza P., Zahradník R.: Collect. Czech. Chem. Commun. 1974, 39, 2857;
2. b) Hobza P., Zahradník R.: Studies in Physical and Theoretical Chemistry, Vol. 52. Elsevier, Amsterdam 1988;
3. c) Hobza P., Zahradník R.: Chem. Rev. 1988, 88, 871;
4. d) Hobza P., Zahradník R.: Int. J. Quantum Chem. 1992, 42, 581.
5. a) Hobza P., Kabeláč M., Šponer J., Mejzlík P., Vondrášek J.: J. Comput. Chem. 1997, 18, 1136;
6. b) Leach A. R.: Molecular Modelling, Principles and Application. Longman, Essex 1996.
7. a) Chesnut D. B., Wormer P. E. S.: Theor. Chim. Acta 1971, 20, 250;
8. b) Mó O., Yanez M., Fernández-Alonso J. I.: J. Phys. Chem. 1975, 79, 137.
9. a) Glauser W. A., Raber D. J., Stevens B.: J. Comput. Chem. 1988, 9, 539;
10. b) Glauser W. A., Raber D. J., Stevens B.: J. Phys. Chem. 1989, 93, 1784;
11. c) Kost D., Frailich M.: J. Mol. Struct. 1997, 398-399, 265.
12. a) Hobza P., Šponer J., Reschel T.: J. Comput. Chem. 1995, 16, 1315;
13. b) Hobza P., Selzle H. L., Schlag E. W.: Collect. Czech. Chem. Commun. 1992, 57, 1186;
14. c) Chipot C., Jaffe R., Maigret B., Pearlman D. A., Kollman P. A.: J. Am. Chem. Soc. 1996, 118, 11217.
15. a) Jaffe R. L., Smith G. D.: J. Chem. Phys. 1996, 105, 2780;
16. b) Tsuzuki S., Uchimaru T., Mikami M., Tanabe K.: Chem. Phys. Lett. 1996, 252, 206.
17. a) Alhambra C., Luque F. J., Gago F., Orozco M.: J. Phys. Chem. B 1997, 101, 3846;
18. b) Saenger W.: Principles of Nucleic Acid Structure, p. 132. Springer. New York 1984.
19. a) Philip D., Stoddart J. F.: Angew. Chem. 1996, 108, 1242, Angew. Chem., Int. Ed. Engl. 1996, 35, 1154;
20. a) Philip D., Stoddart J. F.: Angew. Chem. 1996, 108, 1242, Angew. Chem., Int. Ed. Engl. 1996, 35, 1154;
21. b) Amabilino D. B., Ashton P. R., Boyd S. E., Lee J. Y., Menzer S., Stoddart J. F., Williams D. J.: Angew. Chem. 1997, 109, 2160, Angew. Chem., Int. Ed. Engl. 1997, 36, 2070;
22. b) Amabilino D. B., Ashton P. R., Boyd S. E., Lee J. Y., Menzer S., Stoddart J. F., Williams D. J.: Angew. Chem. 1997, 109, 2160, Angew. Chem., Int. Ed. Engl. 1997, 36, 2070;
23. c) Ashton P. R., Collins A. N., Fyfe M. C. T., Menzer S., Stoddart J. F., Williams D. J.: Angew. Chem. 1997, 109, 760, Angew. Chem., Int. Ed. Engl. 1997, 36, 735;
24. c) Ashton P. R., Collins A. N., Fyfe M. C. T., Menzer S., Stoddart J. F., Williams D. J.: Angew. Chem. 1997, 109, 760, Angew. Chem., Int. Ed. Engl. 1997, 36, 735;
25. d) Jäger R., Voegtle F.: Angew. Chem. 1997, 109, 966, Angew. Chem., Int. Ed. Engl. 1997, 36, 930; and references therein.
26. d) Jäger R., Voegtle F.: Angew. Chem. 1997, 109, 966, Angew. Chem., Int. Ed. Engl. 1997, 36, 930; and references therein.
27. a) Rao C. N. R., Bhat S. N., Dwivedi P. C.: Appl. Spectrosc. Rev. 1971, 5, 1;
28. b) Foster R. in: Organic Chemistry (A. T. Blomquist, Ed.), Vol. 15. Academic Press, London 1969.
29. Dewar M. J. S., Thompson C. C., Jr.: Tetrahedron 1966, Suppl. 7, 97; and references therein.
30. Mulliken R. S., Person W. B.: Molecular Complexes. Wiley, New York 1969.
31. a) Hunter C. A., Sanders J. K. M.: J. Am. Chem. Soc. 1990, 112, 5525;
32. b) Hunter C. A.: Chem. Soc. Rev. 1994, 23, 101;
33. c) Hunter C. A.: Angew. Chem. 1993, 105, 1653, Angew. Chem., Int. Ed. Engl. 1993, 32, 1584.
34. c) Hunter C. A.: Angew. Chem. 1993, 105, 1653, Angew. Chem., Int. Ed. Engl. 1993, 32, 1584.
35. Timoneda J. J., Peters K. S.: J. Phys. Chem. 1996, 100, 16864.
36. a) Bechgaard K. in: Studies in Physical and Theoretical Chemistry (M. Pierrot, Ed.), Vol. 69, Chap. 5, p. 235. Elsevier, Amsterdam 1990;
37. b) Papavassilion G. C., Terzis A., Delhaes P. in: Handbook of Organic Conductive Molecules and Polymers (H. S. Nalwa, Ed.), Vol. 1, Chap. 3, p. 150. Wiley, Chichester 1997;
38. c) Wudl F.: Pure Appl. Chem. 1982, 54, 1051; and references therein.
39. a) Demiralp E., Goddard III W. A.: J. Phys. Chem. A 1997, 101, 8128;
40. b) Nonella M.: J. Phys. Chem. 1996, 100, 20148;
41. c) Adant C., Bredas J. L., Dupuis M.: J. Phys. Chem. A 1997, 101, 3025.
42. Cavallone F., Clementi E.: J. Chem. Phys. 1975, 63, 4304.
43. Emery L. C., Sheldon J. M., Edwards W. D., McHale J. L.: Spectrochim. Acta, Part A 1992, 48, 715.
44. Cioslowski J., Mixon S. T., Edwards W. D.: J. Am. Chem. Soc. 1991, 113, 1083.
45. Hayashi M., Yang T.-S., Yu J., Mebel A., Lin S. H.: J. Phys. Chem. A 1997, 101, 4156.
46. Kohn W., Becke A. D., Parr R. G.: J. Phys. Chem. 1996, 100, 12974.
47. a) Pérez-Jordá J., Becke A. D.: Chem. Phys. Lett. 1995, 233, 134;
48. b) Krystyán S., Pulay P.: Chem. Phys. Lett. 1995, 229, 175.
49. a) Ruiz E., Salahub D. R., Vela A.: J. Phys. Chem. 1996, 100, 12265;
50. b) Ruiz E., Salahub D. R., Vela A.: J. Am. Chem. Soc. 1995, 117, 1141.
51. a) Starikov E. B.: Int. J. Quantum Chem. 1998, 66, 47;
52. b) Starikov E. B.: Int. J. Quantum Chem. 1998, 66, 69.
53. Bryce M. R.: Chem. Soc. Rev. 1991, 20, 355; and references therein.
54. a) Ciccarese A., Clemente D. A., Marzotto A., Pecile C.: Microsc. Microanal. Microstruct. 1995, 6, 545;
55. b) Clemente D. A., Marzotto A.: J. Mater. Chem. 1996, 6, 941; and references therein.
56. a) Kistenmacher T., Phillips T. E., Cowan D. O.: Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1974, 30, 763;
57. b) Ferraris J., Cowan D. O., Walatka V. V., Perlstein J. H.: J. Am. Chem. Soc. 1973, 95, 948.
58. a) Bechgaard K., Kistenmacher T. J., Bloch A. N., Cowan D. O.: Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1977, 33, 417;
59. b) Engler E. M., Patel V. V.: J. Am. Chem. Soc. 1974, 96, 7376.
60. a) Tanaka K., Sato T., Yamabe T.: J. Phys. Chem. 1996, 100, 3980;
61. b) Saito G., Teramoto T., Otsuka A., Sugita Y., Ban T., Kusunoki M., Sakaguchi K.: Synth. Met. 1994, 64, 359.
62. Frisch J. M., Trucks G. W., Schlegel H. B., Gill P. M. W., Johnson B. G., Robb M. A., Cheeseman J. R., Keith T., Petersson G. A., Montgomery J. A., Raghavachari K., Al-Laham M. A., Zakrzewski V. G., Ortiz J. V., Foresman J. B., Cioslowski J., Stefanov B. B., Nanayakkara A., Challacombe M., Peng C. Y., Ayala P. Y., Chen W., Wong M. W., Andres J. L., Replogle E. S., Gomperts R., Martin R. L., Fox D. J., Binkley J. S., Defrees D. J., Baker J., Stewart J. P., Head-Gordon M., Gonzalez, C., Pople J. A.: GAUSSIAN 94. Revision B.2. Gaussian, Inc., Pittsburgh, PA 1995.
63. a) Hehre W. J., Radom L., v. R. Schleyer P., Pople J. A.: Ab initio Molecular Orbital Theory. Wiley, New York 1986;
64. b) Bartlett R. J., Stanton J. F. in: Reviews in Computational Chemistry (K. B. Lipkowitz and D. B. Boyd, Eds), Vol. 5, Chap. 2, p. 65. VCH, New York 1994.
65. Becke A. D.: J. Chem. Phys: 1993, 98, 5648.
66. Boys S. F., Bernardi F.: Mol. Phys. 1970, 19, 553.
67. a) Sponer J., Leszczynski J., Hobza P.: J. Phys. Chem. 1996, 100, 5590;
68. b) Šponer J., Gabb H. A., Leszczynski J., Hobza P.: Biophys. J. 1997, 73, 76; and references therein.
69. Reed A. E., Curtiss L. A., Weinhold F.: Chem. Rev. 1988, 88, 899.
70. Glendening E. D., Badenhoop J. K., Reed A. E., Carpenter J. E., Weinhold F.: NBO 4.0. Theoretical Chemistry Institute, University of Wisconsin, Madison, WI 1996.
71. a) Miertus S., Scrocco E., Tomasi J.: Chem. Phys. 1981, 55, 117;
72. b) Tomasi J., Persico M.: Chem. Rev. 1994, 94, 2027.
73. Hope H.: Acta Chem. Scand. 1968, 22, 1057.
74. Becker P., Coppens P., Ross F. K.: J. Am. Chem. Soc. 1973, 95, 7604.
75. a) Chowdhury S., Kebarle P.: J. Am. Chem. Soc. 1986, 108, 5453;
76. b) Kebarle P., Chowdhury S.: Chem. Rev. 1987, 87, 513;
77. c) Lide D. R. in: CRC Handbook of Chemistry and Physics (D. R. Lide and A. P. R. Frederikse, Eds), 75th ed., p. 10. CRC Press, Boca Raton 1994.
78. Hargittai I., Brunvoll J., Kolonits M., Khodorkovsky V.: J. Mol. Struct. 1994, 317, 273.
79. a) Kistenmacher T. J., Emge T. J., Shu P., Cowan D. O.: Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1979, 35, 772;
80. b) Thorup N., Rindorf G., Soling H.: Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1981, 37, 1236.
81. a) Bock H., Borrmann H., Havlas Z., Oberhammer H., Ruppert K., Simon A.: Angew. Chem. 1991, 103, 1733, Angew. Chem., Int. Ed. Engl. 1991, 30, 1678;
82. a) Bock H., Borrmann H., Havlas Z., Oberhammer H., Ruppert K., Simon A.: Angew. Chem. 1991, 103, 1733, Angew. Chem., Int. Ed. Engl. 1991, 30, 1678;
83. b) Bruckmann J., Krüger C., Borrmann H., Simon A., Bock H.: Z. Kristallogr. 1995, 210, 521;
84. c) Kuwata K., Geske D. H.: J. Am. Chem. Soc. 1964, 86, 2101.
85. Streitwieser A., Jr.: Molecular Orbital Theory for Organic Chemists, Chap. 7. Wiley, New York 1961.
86. 1,3,1′,3′-Tetramethyloctahydro[2,2′]bisimidazolylidene: Nakato Y., Ozaki M., Egawa A., Tsubomura H.: Chem. Phys. Lett. 1971, 9, 615.
87. a) Gleiter R., Spanget-Larsen J.: Top. Curr. Chem. 1979, 86, 139;
88. b) Bock H., Roth B., Sumaker R.: Phosphorus Sulfur 1984, 21, 79.
89. Sato N., Saito G., Inokuchi H.: Chem. Phys. 1983, 76, 79.