Interanionic (-)O - H⋯O(-) interactions: A solid-state and computational study of the ring and chain motifs

Chemistry - A European Journal

Volumn 6, Issue 24, 2000, Pages 4536-4551

  Braga, Dario ^a   Maini, Lucia ^a   Grepioni, Fabrizia ^b   Mota, Fernando ^c   Rovira, Carme ^c   Novoa, Juan J ^c  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF SASSARI   (Italy)

^c UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Ab initio calculations; Database analysis; Deprotonated acids; Hydrogen bonds; Ion molecule interactions; Isomers

Indexed keywords

ANION; BICARBONATE; WATER;

ARTICLE; COMPUTER ANALYSIS; DATA BASE; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR RECOGNITION;

EID: 0034671368     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20001215)6:24<4536::AID-CHEM4536>3.0.CO;2-M     Document Type: Article

References (85)

1. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, New York, 1997.
2. a) M. C. Etter, Acc. Chem. Res. 1990, 23, 120;
3. b) J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. 1995, 107, 1689; Angew. Chem. Int. Ed. Engl. 1995, 34, 1555.
4. b) J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. 1995, 107, 1689; Angew. Chem. Int. Ed. Engl. 1995, 34, 1555.
5. G. R. Desiraju, Angew. Chem. 1995, 107, 2541; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311.
6. G. R. Desiraju, Angew. Chem. 1995, 107, 2541; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311.
7. M.S. Gordon, J. H. Jensen, Acc. Chem. Res. 1996, 29, 536, and references cited therein.
8. H. Umeyama, K. Morokuma, J. Am. Chem. Soc. 1977, 99, 1316.
9. a) G. Gilli, F. Bellucci, V. Ferretti, V. Bertolasi, J. Am. Chem. Soc. 1989, 111, 1023;
10. b) V. Bertolasi, P. Gilli, V. Ferretti, G. Gilli, Chem. Eur. J. 1996, 8, 925, and references cited therein.
11. See for example: a) M. Meot-Ner (Mautner) J. Am. Chem. Soc. 1984, 106, 1257;
12. b) M. Meot-Ner (Mautner), L. W. Sieck, J. Am. Chem. Soc. 1986, 108, 7525.
13. a) D. Braga, F. Grepioni, J. Chem. Soc. Dalton Trans. 1999, 1;
14. b) M. W. Hosseini, A. De Cian, Chem. Commun. 1998, 727;
15. c) L. Brammer, D. Zhao, F. T. Ladipo, J. Braddock-Wilking, Acta Crystallogr. Sect. B 1995, 51, 632;
16. d) C. B. Aakeröy, Acta Crystallogr. Sect. B 1997, 53, 569;
17. e) D. Braga, F. Grepioni, Chem. Commun. 1996, 571;
18. f) D. Braga, F. Grepioni, New J. Chem. 1998, 1159.
19. a) Crystal Engineering: from Molecules and Crystals to Materials (Eds: D. Braga, F. Grepioni, A. G. Orpen), Kluwer Academic, Dordrecht, 1999;
20. b) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375.
21. D. Braga, F. Grepioni, Acc. Chem. Res. 2000, 33, 601.
22. a) D. Braga, F. Grepioni, E. Tagliavini, J. J. Novoa, F. Mota, New. J. Chem. 1998, 755;
23. b) J. J. Novoa, I. Nobeli, F. Grepioni, D. Braga, New J. Chem. 2000, 24, 5.
24. L. Pauling, The Nature of the Chemical Bond, Cornell University Press, Ithaca, NY, 1960, p. 6.
25. D. Braga, F. Grepioni, J. J. Novoa, Chem. Commun. 1998, 1959.
26. a) T. Steiner, Chem. Commun. 1999, 2299;
27. b) M. Mascal, C. E. Marajo, A. J. Blake, Chem. Commun. 2000, 1591;
28. c) P. Macchi, B. B. Iversen, A. Sironi, B. C. Chokoumakas, F. K. Larsen, Angew. Chem. 2000, 112, 2831; Angew. Chem. Int. Ed. 2000, 39, 2719.
29. c) P. Macchi, B. B. Iversen, A. Sironi, B. C. Chokoumakas, F. K. Larsen, Angew. Chem. 2000, 112, 2831; Angew. Chem. Int. Ed. 2000, 39, 2719.
30. D. Braga, F. Grepioni, J. J. Novoa, New J. Chem., in press.
31. 5 has been redetermined in order to obtain a more accurate data set; previous determination: N. C. Baezinger, D. G. Williams, J. Am. Chem. Soc. 1966, 88, 689.
32. a) J. J. Novoa, M. Deumal, Mol. Cryst. Liq. Cryst. 1997, 305, 143;
33. b) M. Deumal, J. Cirujeda, J. Veciana, M. Kinoshita, Y. Hosokoshi, J. J. Novoa, Chem. Phys. Lett. 1997, 265, 190;
34. c) Implications of Molecular and Materials Structure for New Technologies (Eds: J. J. Novoa, F. Allen, J. Howard), Kluwer Academic, Dordrecht, 1999;
35. d) C. Lee, G. Fitzgerald, M. Planas, J. J. Novoa, J. Phys. Chem. 1996, 100, 7398.
36. a) F. H. Allen, O. Kennard, Chem. Des. Autom. News 1993, 8, 31;
37. b) Inorganic Crystal Structure Database (ICSD), Fachinformations-zentrum (FIZ) Karlsruhe and Gmelin Institut, Release 99/2.
38. a) L. Leiserowitz and G. M. J. Schmidt, J. Chem. Soc. A 1969, 2372;
39. b) L. Leiserowitz Acta Crystallogr. Sect B 1976, 32, 775;
40. c) Z. Berkovitch-Yellin, L. Leiserowitz, J. Am. Chem. Soc. 1982, 104, 4064.
41. O. N. Ventura, J. B. Rama, L. Turi, J. J. Dannenberg, J. Phys. Chem. 1995, 99, 131.
42. a) A.Gavezzotti, Chem. Eur. J. 1999, 5, 567;
43. b) A. Gavezzotti, G. Filippini, J. Kroon, B. P. van Eijck, P. Klewinghaus Chem. Eur. J. 1997, 3, 893.
44. F. H. Allen, W. D. S. Motherwell, P. R. Raithby, G. P. Shields, R. Taylor, New J. Chem. 1999, 25.
45. I. Nahringbauer, Acta Crystallogr. Sect. B 1970, 24, 453.
46. a) L. Turi, J. J. Dannenberg, J. Am. Chem. Soc. 1993, 97, 12197;
47. b) L. Turi, J. J. Dannenberg, J. Am. Chem. Soc. 1994, 116, 8714.
48. J. C. Derrissen, P. H. Smit Acta Crystallogr. Sect. B 1974, 30, 2240.
49. D. Braga, F. Grepioni, P. Sabatino, G. R. Desiraju, Organometallics 1994, 13, 3532.
50. B. D. Sharma, Acta Crystallogr. 1965, 18, 818.
51. I. C. Hayes, A. J. Stone, Mol. Phys. 1984, 53, 83; computed by using the Cadpac 6.1 , included as part of the Unichem 4.1 suite.
52. -.
53. a) R. Car, M. Parrinello, Phys. Rev. Lett., 1985, 55, 2471;
54. b) G. Galli, M. Parrinello in Computer Simulation in Materials Science (Eds: V. Pontikis, M. Meyer), Kluwer Academic, Dordrecht, 1991.
55. a) A. D. Becke, J. Chem. Phys. 1986, 84, 4524.
56. b) J. P. Perdew, Phys. Rev. B, 1986, 33, 8822.
57. V. R. Saunders, R. Dovesi, C. Roetti, M. Causa, N. M. Harrison, R. Orlando, C. M. Zicovich-Wilson, CRYSTAL 98 User's Manual, University of Torino, Torino 1998.
58. Some amount of covalency was seen to be necessary to reproduce the experimental X-ray diffraction patters in ice, which was not possible to be reproduced by purely electrostatic (ionic) models. Covalency was accounted for by allowing the combination of the orbitals of the water fragments. E. D. Isaacs, A. Shukla, P. M. Platzman, D. R. Hamann, B. Barbiellini, C. A. Tulk, Phys. Rev. Lett. 1999, 82, 600.
59. R. F. W. Bader, Atoms in Molecule. A Quantum Theory, Clarendon, Oxford, 1990.
60. V. G. Tsirelson, P. F. Zou, T.-H. Tang, R. F. W. Bader, Acta Crystallogr Sect. A. 1995, 51, 143.
61. - dimer, at any distance between the two anions.
62. a) J. Cioslowski, S. T. Mixon, J. Am. Chem. Soc. 1992, 114, 4382;
63. b) J. Cioslowski, P. B. O'Connor, E. D. Fleishmann, J. Am. Chem. Soc. 1991, 113, 1086;
64. c) J. Cioslowski, S. T. Mixon, W. D. Edwards, J. Am. Chem. Soc. 1991, 113, 1083.
65. a) J. Dunitz, J. Bernstein, Acc. Chem. Res. 1995, 28, 193;
66. b) J. Bernstein, R. J. Davey, J.-O. Henck, Angew. Chem. 1999, 111, 3646; Angew. Chem. Int. Ed. 1999, 38, 3440.
67. b) J. Bernstein, R. J. Davey, J.-O. Henck, Angew. Chem. 1999, 111, 3646; Angew. Chem. Int. Ed. 1999, 38, 3440.
68. D. Braga, C. Bazzi, F. Grepioni, J. J. Novoa, New J. Chem. 1999, 23, 577.
69. a) W. Matsui, Acta Crystallogr. Sect. B 1978, 34, 2731;
70. b) H. Fuess, N. Burger, J. W. Bats, Z. Kristallogr. 1981, 156, 219;
71. c) S. Onuma, S. Shibata, Fac. Sci. Shizuoka Univ. 1978, 12, 45.
72. J. E. Huheey, E. A. Keiter, R. L. Keiter, Inorganic Chemistry, 4th ed., Harper Collins, New York, 1993.
73. J. D. Dunitz, A. Gavezzotti, Acc. Chem. Res. 1999, 32, 677.
74. J. M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995.
75. a) G. M. Sheldrick, SHELXL97, Program for Crystal Structure Determination, University of Göttingen, Göttingen, Germany, 1997;
76. b) E. Keller, SCHAKAL97, Graphical Representation of Molecular Models ; University of Freiburg, Freidberg, Germany, 1997.
77. a) M. J. Frisch, G. W.Trucks, H. B Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Peterson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Ciolowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian94, Revision C.3, Gaussian, Pittsburgh PA, 1995;
78. b) S. Huzinaga, Gaussian Basis Sets for Molecular Calculations, Elsevier, Amsterdam 1984.
79. a) J. J. Novoa, M. Deumal, Mol. Cryst. Liq. Cryst. 1997, 305, 143;
80. b) M. Deumal, J. Cirujeda, J. Veciana, M. Kinoshita, Y. Hosokoshi, J. J. Novoa, Chem. Phys. Lett. 1997, 265, 190;
81. c) J. J. Novoa in Implications of Molecular and Materials Structure for New Technologies (Eds.: F. Allen, J. Howard), Kluwer Academic, Dordrecht, 1999.
82. a) A. J. Stone, Chem. Phys. Lett. 1981, 83, 233;
83. b) S. L. Price, A. J. Stone, Chem. Phys. Lett. 1983, 98, 419.
84. F. Biegle-Koning, R. F. W. Bader, W.-H. Tang, J. Comput. Chem. 1982, 3, 317.
85. N. Troullier, J. L. Martins Phys. Rev. B. 1991, 43, 1993.