A DFT study of tin- and crown-ether-based host molecules capable of binding anions and cations simultaneously

European Journal of Inorganic Chemistry

Volumn , Issue 7, 2003, Pages 1315-1324

  Vivas Reyes, Ricardo ^a,b   De Proft, Frank ^b   Biesemans, Monique ^b   Willem, Rudolph ^b   Geerlings, Paul ^b  

^a UNIVERSIDAD DE CARTAGENA   (Colombia)

^b VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

Acidity; Basicity; Crown compounds; Density functional calculations; Host guest systems; Tin

Indexed keywords

ACETONE; ALKALINITY; ATOMS; CROWN ETHERS; ELECTROSTATICS; ETHERS; HARDNESS; LIGANDS; MOLECULES; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS; TIN; TIN COMPOUNDS;

BASIS SETS; CROWN COMPOUNDS; CROWN-ETHERS; DENSITY-FUNCTIONAL CALCULATIONS; DFT CALCULATION; FUKUI FUNCTIONS; HOST/GUEST SYSTEMS; LOCAL SOFTNESS; REACTIVITY DESCRIPTOR; TIN ATOMS;

DENSITY FUNCTIONAL THEORY;

ANION; CARBON; CATION; CROWN ETHER; NITROGEN; OXYGEN; POTASSIUM ION; PROTON; SODIUM ION; SULFUR; TIN; WATER;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL INTERACTION; ELECTROCHEMICAL ANALYSIS; ION CONDUCTANCE; IONIC STRENGTH; MOLECULAR INTERACTION; MOLECULE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THEORETICAL STUDY;

EID: 0037395160     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200390171     Document Type: Article

References (96)

1. [1a] I. Haiduc, F. T. Edelmann, in Supramolecular Organometallic Chemistry, Wiley-VCH, Weinheim, 1999, pp. 42-43.
2. [1b] N. Pelizzi, A. Casnati, A. Friggeri, R. Ungaro, J. Chem. Soc. Perkin Trans. 2 1998, 1307-1311.
3. [1c] P. D. Beer, J. B. Cooper, Chem. Commun. 1998, 129-130.
4. [1d] P. D. Beer, S. W. Dent, Chem. Commun. 1998, 825-826.
5. [1e] M. T. Blanda, M. A. Herren, Chem. Commun. 2000, 343-344.
6. [1f] J. E. Redman, P. D. Beer, S. W. Dent, M. G. B. Drew, Chem. Commun. 1998, 231-232.
7. [1g] M. T. Reetz, C. M. Niemeyer, K. Harms, Angew. Chem. Int. Ed. Engl. 1991, 30, 1472-1474.
8. [1h] M. T. Reetz, C. M. Niemeyer, K. Harms, Angew. Chem. Int. Ed. Engl. 1991, 30, 1474-1476.
9. [1i] J. Scheerder, J. P. M. van Duynhoven, J. F. J. Engbersen, D. N. Reinhoudt, Angew. Chem. Int. Ed. Engl. 1996, 35, 1090-1093.
10. [1j] D. M. Rudkevich, Z. Brzozka, M. Palys, H. C. Visser, W. Verboom, D. N. Reinhoudt, Angew. Chem. Int. Ed. Engl. 1994, 33, 467-468.
11. [1k] J. M. Lehn, in La chimie supramoléculaire, Deboeck Université, Paris, 1997, p. 37.
12. [2a] D. J. Cram, Science 1988, 240, 760-767.
13. [2b] J. J. Christensen, D. J. Eatough, R. M. Izatt, Chem. Rev. 1974, 74, 351-384.
14. [2c] R. M. Izatt, K. Pawlak, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1991, 91, 1721-2085.
15. [3a] M. F. Hawthorne, X. Yang, Z. Zheng, Pure Appl. Chem. 1994, 66, 245-254.
16. [3b] B. Dietrich, Pure Appl. Chem. 1993, 65, 1457-1464.
17. [3c] F. D. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
18. [4a] Crown ethers and analogs (Ed.: S. Pataï), John Wiley & Sons, Chichester, 1989.
19. [4b] F. Vögtle, in Supramolecular Chemistry, John Wiley & Sons, Chichester, 1991.
20. [4c] Comprehensive Supramolecular Chemistry, vol. I-XI (Eds.: J. M. Lehn, J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle), Pergamon, Oxford, 1996.
21. [5a] T. J. Karol, J. P. Hutchinson, J. R. Hyde, H. G. Kuivila, J. A. Zubieta, Organometallics 1983, 2, 106-114.
22. [5b] M. Gielen, K. Jurkschat, J. Organomet. Chem. 1984, 273, 303-312.
23. [5c] M. Austin, K. Gebreyes, H. G. Kuivila, K. Swami, J. A. Zubieta, Organometallics 1987, 6, 834-842.
24. [5d] K. Jurkschat, H. G. Kuivila, S. Liu, J. A. Zubieta, Organometallics 1989, 8, 2755-2759.
25. [5e] J. H. Horner, P. J. Squatritto, N. McGuire, J. P. Riebenspies, M. Newcomb, Organometallics 1991, 10, 1741-1750.
26. [5f] D. Dakternieks, K. Jurkschat, H. Zhu, E. R. T. Tiekink, Organometallics 1995, 14, 2512-2521.
27. [5g] R. Altmann, K. Jurkschat, M. Schürmann, D. Dakternieks, A. Duthie, Organometallics 1997, 16, 5716-5723.
28. [5h] R. Altmann, O. Gausset, D. Horn, K. Jurkschat, M. Schürmann, M. Fontani, P. Zanello, Organometallics 2000, 19, 430-443.
29. [6a] C. H. Yoder, R. A. Morreall, C. I. Butoi, W. J. Kowalski, J. N. Spencer, J. Organomet. Chem. 1993, 448, 59-61.
30. [6b] S. W. Ng, J. M. Hook, M. Gielen, Main Group Met. Chem. 1999, 22, 649-654.
31. [6c] S. W. Ng, Z. Kristallogr. 1999, 214, 424-426.
32. [6d] J. K. Tsagatakis, N. A. Chaniotakis, K. Jurkschat, S. Damoun, P. Geerlings, A. Bouhdid, M. Gielen, I. Verbruggen, M. Biesemans, J. C. Martins, R. Willem, Helv. Chim. Acta 1999, 82, 531-542.
33. [7a] M. Gielen, Coord. Chem. Rev. 1996, 151, 41-51.
34. [7b] M. Gielen, P. Lelieveld, D. de Vos, R. Willem, in Metal Complexes in Cancer Chemotherapy (Ed.: B. K. Keppler), VCH, Weinheim, 1993, pp. 383-390.
35. [7c] D. de Vos, R. Willem, M. Gielen, K. E. van Wingerden, K. Nooter, Met. Based Drugs 1998, 5, 179-188.
36. [8a] E. R. T. Tiekink, Appl. Organomet. Chem. 1991, 5, 1-23.
37. [8b] E. R. T. Tiekink, Trends Organomet. Chem. 1994, 1, 71-116.
38. M. Kemmer, M. Biesemans, M. Gielen, J. C. Martins, V. Gramlich, R. Willem, Chem. Eur. J. 2001, 17, 4686-4695.
39. [10a] A. Marquez, G. G. Gonzalez, J. Fernandez-Sanz, Chem. Phys. 1989, 138, 99-104.
40. [10b] G. Stewart, E. R. T. Tiekink, M. A. Buntine, J. Phys. Chem. 1997, 101, 5638-5373.
41. [10c] M. A. Buntine, V. J. Hall, F. J. Kosovel, E. R. T. Tiekink, J. Phys. Chem. A 1998, 102, 2472-2482.
42. [10d] J. Leszczynki, I. J. Yanov, J. Phys. Chem. A. 1999, 103, 396-401.
43. [10e] G. Barone, M. C. Ramusino, R. Barbieri, G. Lamanna, J. Mol. Struct. (Theochem). 1999, 469, 143-149.
44. [10f] M. Yasuda, K. Chiba, A. Baba, J. Am. Chem. Soc. 2000, 122, 7549-7555.
45. [10g] D. Duca, G. Barone, G. La Manna, T. Fiore, C. Pellerito, R. Di Stefano, M. Scopello, L. Pellerito, Appl. Organomet. Chem. 2001, 15, 581.
46. S. Krishnamurty, R. K. Roy, R. Vetrivel, S. Iwata, S. Pal, J. Phys. Chem. 1997, 101, 7253-7257.
47. R. Ch. Deka, R. Vetrivel, S. Pal, J. Phys. Chem. 1999, 103, 5978-5982.
48. S. Pal, K. R. S. Chandrakumar, J. Am. Chem. Soc. 2000, 122, 4145-4153.
49. R. K. Roy, S. Krishnnamurty, P. Geerlings, S. Pal, J. Phys. Chem. 1998, 102, 3746-3755.
50. S. Damoun, W. Langenaeker, P. Geerlings, J. Phys. Chem. 1997, 101, 6951-6954.
51. S. Damoun, G. Van de Woude, F. Mendez, P. Geerlings, J. Phys. Chem. 1997, 101, 886-893.
52. S. Damoun, G. Van de Woude, K. Choho, P. Geerlings, J. Phys. Chem. 1999, 103, 7861-7866.
53. [18a] R. G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
54. [18b] H. Chermette, J. Comp. Chem. 1999, 20, 129.
55. [18c] F. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev., in press.
56. [18d] F. De Proft, P. Geerlings, Chem. Rev. 2001, 101, 1451-1464.
57. [18e] P. Geerlings, F. De Proft, Int. J. Mol. Sci. 2002, 3, 276-309.
58. R. G. Parr, R. G. Pearson, J. Am. Chem. Soc. 1983, 105, 7512-7516.
59. R. G. Pearson, J. Am. Chem. Soc. 1963, 85, 3533-3539.
60. R. G. Pearson, Coord. Chem. Rev. 1990, 100, 403-425.
61. R. G. Parr, P. K. Chattaraj, J. Am. Chem. Soc. 1991, 113, 1855-1856.
62. R. G. Parr, P. K. Chattaraj, J. Am. Chem. Soc. 1991, 113, 1854-1855.
63. P. K. Chattaraj, G. H. Liu, R. G. Parr, Chem. Phys. Lett. 1995, 237, 171-176.
64. [25a] R. G. Parr, W. Yang, J. Am. Chem. Soc. 1984, 106, 4049-4050.
65. [25b] W. Yang, R. G. Parr, Proc. Natl. Acad. Sci. USA 1985, 82, 6723-6726.
66. W. Yang, W. J. Mortier, J. Am. Chem. Soc. 1986, 108, 5708-5711.
67. R. Vivas-Reyes, F. De Proft, M. Biesemans, R. Willem, P. Geerlings, J. Phys. Chem. A 2002, 106, 2753-2759.
68. R. Vivas-Reyes, F. De Proft, P. Geerlings, M. Biesemans, R. Willem, F. Ribot, C. Sanchez, New. J. Chem. 2002, 9, 1108-1117.
69. P. Geerlings, F. De Proft, W. Langenaeker, in Density Functional Methods: Applications in Chemistry and Material Science (Ed.: M. Springborg), chapter 2, John Wiley, New York, 1997.
70. P. Geerlings, F. De Proft, W. Langenaeker, Adv. Quant. Chem. 1999, 33, 303-328.
71. J. L. Gazquez, F. Mendez, J. Chem. Phys. 1994, 98, 4591-4593.
72. F. Mendez, J. Tamariz, P. Geerlings, J. Phys. Chem. A 1998, 102, 6292-6296.
73. F. Mendez, M. L. de Romero, F. De Proft, P. Geerlings, J. Org. Chem. 1998, 63, 5774-5778.
74. T. N. Le, L. T. Nguyen, F. De Proft, A. K. Chandra, P. Geerlings, M. T. Nguyen, J. Chem. Soc., Perkin Trans. 2 1999, 1249-1255.
75. R. Bonaccorsi, E. Scrocco, J. Tomasi, J. Chem. Phys. 1970, 51, 5270-5284.
76. M. M. Rohmer, M. Bénard, J. P. Blaudeau, J. P. Maestre, J. M. Poblet, Coord. Chem. Rev. 1998, 178-180, 1015-1045, and refs. cited therein.
77. J. Tomasi, B. Menuci, R. Cammi, in Molecular Electrostatic Potentials: Concepts and Applications, Theoretical and Computational Chemistry, (Eds.: J. S. Murray, K. D. Sen), Elsevier, Amsterdam, 1996, vol. 3.
78. P. Geerlings, F. De Proft, Int. J. Quant. Chem. 2000, 80, 227-235.
79. C. Lee, W. Yang, R. G. Parr, J. Mol. Struct. 1988, 163, 305-313.
80. R. S. Mulliken, J. Chem. Phys. 1955, 23, 1833-1840.
81. 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.
82. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
83. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B. 1998, 37, 785-789.
84. P. J. Stephens, F. J. Delvin, C. F. Chablowski, M. J. Frisch, J Phys. Chem. 1994, 98, 11623-11627.
85. W. J. Hehre, L. Radom, P. V. R. Schleyer, J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
86. F. Vögtle, Supramolecular Chemistry, John Wiley & Sons, New York, 1993.
87. P. Geerlings, F. De Proft, J. M. L. Martin, in Theoretical and Computational Chemistry, vol.4 ("Recent Developments and Applications of Modern Density Functional Theory") (Ed.: J. M. Seminario), Elsevier, Amsterdam, 1996, p. 773.
88. D. Gonnissen, W. Langenaeker, A. Hubin, P. Geerlings, J. Raman Spectrosc. 1998, 29, 1031-1039.
89. F. Tielens, M. Saeys, E. Tourwé, G. B. Marin, A. Hubin, P. Geerlings, J. Phys. Chem. A 2002, 106, 1450-1457.
90. R. F. W. Bader, Atoms in Molecules, A Quantum Theory, Clarendon Press, Oxford, 1990, p. 192.
91. G. Klopman, J. Am. Chem. Soc. 1968, 90, 223-234.
92. [52a] N. Pieper, C. Klaus-Mrestani, M. Schürmann, K. Jurkschat, M. Biesemans, I. Verbruggen, J. C. Martins, R. Willem, Organometallics 1997, 16, 1043-1052.
93. [52b] A. Meddour, F. Mercier, J. C. Martins, M. Gielen, M. Biesemans, R. Willem, Inorg. Chem. 1997, 36, 5712-5715.
94. [52c] J. Beckmann, M. Biesemans, K. Hassler, K. Jurkschat, J. C. Martins, M. Schürmann, R. Willem, Inorg. Chem. 1998, 37, 4891-4897.
95. [52d] F. A. G. Mercier, A. Meddour, M. Gielen, M. Biesemans, R. Willem, E. R. T. Tiekink, Organometallics 1998, 17, 5933-5936.
96. E. J. Gabe, F. L. Lee, L. E. Khoo, F. E. Smith, Inorg. Chim. Acta 1986, 112, 41-46.