Structural Motifs in Secondary Ammonium Halides: Ring-Stacking and Ring-Laddering in the Organic Solid State

Chemistry - A European Journal

Volumn 10, Issue 8, 2004, Pages 1885-1898

  Bond, Andrew D ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

Database; Halides; Hydrogen bonds; Ring stacking ring laddering; Searching; Solid state structure

Indexed keywords

ASSOCIATION REACTIONS; CRYSTAL STRUCTURE; HYDROGEN BONDS; MOLECULAR STRUCTURE; STEREOCHEMISTRY;

RING STACKING; STRUCTURAL ORGANIC CHEMISTRY;

AMMONIUM COMPOUNDS;

ALKALI METAL; AMMONIUM DERIVATIVE; CHLORIDE; HALIDE; HYDROGEN; NITROGEN; ORGANIC COMPOUND;

CHEMICAL BINDING; HYDROGEN BOND; MOLECULAR INTERACTION; REVIEW; SOLID STATE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 2342419778     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305700     Document Type: Review

References (86)

1. a) D. Barr, W. Clegg, R. E. Mulvey, R. Snaith, K. Wade, J. Chem. Soc. Chem. Commun. 1986, 295;
2. b) D. R. Armstrong, D. Barr, W. Clegg, R. E. Mulvey, D. Reed, R. Snaith, K. Wade, J. Chem. Soc. Chem Commun. 1986, 869.
3. Review articles: a) K. Gregory, P. von R. Schleyer, R. Snaith, Adv. Inorg. Chem. 1991, 37, 47;
4. b) R. E. Mulvey, Chem. Soc. Rev. 1991, 20, 167;
5. c) R. E. Mulvey, Chem. Soc. Rev. 1998, 27, 339;
6. d) A. Downard, T. Chivers, Eur. J. Inorg. Chem. 2001, 2193.
7. P.B. Hitchcock, M. F. Lappert, W.-P. Leung, D.-S. Liu, T. C. W. Mak, Z.-X. Wang, J. Chem. Soc. Dalton Trans. 1999, 1263 (CSD refcode: LAJQAO).
8. D. R. Armstrong, D. Barr, R. Snaith, W. Clegg, R. E. Mulvey, K. Wade, D. Reed, J. Chem. Soc Dalton Trans. 1987, 1071 (DIFGUU10).
9. D. Armstrong, D. Barr, W. Clegg, S. M. Hodgson, R. E. Mulvey, D. Reed, R. Snaith, D. S. Wright, J. Am. Chem. Soc. 1989, 111, 4719 (KARTOM).
10. W. Clegg, K. W. Henderson, L. Horsburgh, F. M. Mackenzie, R. E. Mulvey, Chem. Eur. J. 1998, 4, 53 (NEXKOQ).
11. D. K. Kennepohl, S. Brooker, G. M. Sheldrick, H. W. Roesky, Chem. Ber. 1991, 124, 2223 (SOLXUM).
12. D. Barr, W. Clegg, R. E. Mulvey, R. Snaith, J. Chem. Soc. Chem. Commun. 1984, 285 (ZEGNII).
13. G. R. Desiraju, Angew. Chem. 1995, 107, 2541; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311.
14. G. R. Desiraju, Angew. Chem. 1995, 107, 2541; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311.
15. A. D. Bond, E. L. Doyle, Chem. Commun. 2003, 2324.
16. H. Chen, R. A. Bartlett, H. V. R. Dias, M. M. Olmstead, P. P. Power, Inorg. Chem. 1991, 30, 3390.
17. F. H. Allen, Acta Crystallogr. Sect. B 2002, 58, 380; CSD Version 5.24, November 2002 (272066 entries), Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
18. F. H. Allen, Acta Crystallogr. Sect. B 2002, 58, 380; CSD Version 5.24, November 2002 (272066 entries), Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
19. - hydrogen-bond motifs are not disrupted by additional hydrogen-bond interactions
20. B. Rees, R. Weiss, Acta Crystallogr. Sect. B 1971, 27, 932 (TMPIPO).
21. The resemblance to the fourfold motif in the Li derivative of 2,2,6,6-tetramethylpiperidine is striking: M. F. Lappert, M. J. Slade, A. Singh, J. L. Atwood, R. D. Rogers, R. Shakir, J. Am. Chem. Soc. 1983, 105, 302 (BUXNUD).
22. R. E. Rosenfield Jr., R. Parthasarathy, J. D. Dunitz, J. Am. Chem. Soc. 1977, 99, 4860.
23. a) H. A. Karapetyan, Y. T. Struchkov, G. G. Dvoryantseva, Cryst. Struct. Commun. 1982, 11, 1441 (BORXUB);
24. b) M. Bukowska-Stzyzewska, W. Dubrowolska, J. Skoweranda, T. Gajda, A. Zwierzak, J. Mol. Struct. 1980, 69, 117 (BRPYRL);
25. c) W. C. Stallings, C. T. Monti, J. P. Glusker, Acta Crystallogr. Sect. B 1982, 38, 177 (CETEAN10);
26. d) M. Yokota, H. Uekusa, Y. Ohashi, Bull. Chem. Soc. Jpn. 1999, 72, 1731 (HOTZOF);
27. e) D. Mondeshka, I. Angelova, B. Stensland, P.-E. Werner, C. Ivanov, Acta Chem. 1992, 46, 54 (PEFCUY);
28. f) J. Ouhabi, M. Saux, A. Carpy, Acta Crystallogr. Sect. C 1990, 46, 2160 (SIFGUJ);
29. g) T. M. Georgiadis, M. M. Georgiadis, F. Diederich, J. Org. Chem. 1991, 56, 3362 (SOBFIY);
30. h) H.-G. Klebe, V. G. Krishnan, A. Weiss, H. Fueß, Eur. Cryst. Meeting 1983, 8, 245 (TAJRUR);
31. i) Z. Jia, J. W. Quail, V. K. Arora, J. R. Dimmock, Acta Crystallogr. Sect. C 1988, 44, 2114 (VABFIN);
32. j) M. Dobler, J. D. Dunitz, Helv. Chim. Acta 1964, 47, 695 (AZNONB);
33. k) K. Frydenvang, L. M. Hansen, B. Jensen, Acta Crystallogr. Sect. C 1995, 51, 2053 (ZENJAD).
34. Averages derived from 352 fragments in 314 structures for the chlorides and 104 fragments in 96 structures for the bromides. See Supporting Information.
35. T. Steiner, Angew. Chem. 2002, 114, 50; Angew. Chem. Int. Ed. 2002, 41, 48.
36. T. Steiner, Angew. Chem. 2002, 114, 50; Angew. Chem. Int. Ed. 2002, 41, 48.
37. a) G. Boche, I. Langlotz, M. Marsch, K. Harms, N. E. S. Nudelman, Angew. Chem. 1992, 104, 1239; Angew. Chem. Int. Ed. Engl. 1992, 31, 1205 (KUPSET);
38. a) G. Boche, I. Langlotz, M. Marsch, K. Harms, N. E. S. Nudelman, Angew. Chem. 1992, 104, 1239; Angew. Chem. Int. Ed. Engl. 1992, 31, 1205 (KUPSET);
39. b) K. W. Henderson, P. G. Williard, Organometallics 1999, 18, 5620 (XEWFIO).
40. 6: R. Snaith, D. Barr, D. S. Wright, W. Clegg, S. M. Hodgson, G. R. Lamming, A. J. Scott, R. E. Mulvey, Angew. Chem. 1989, 101, 1279; Angew. Chem. Int. Ed. Engl. 1989, 28, 1241 (SEDVEC).
41. 6: R. Snaith, D. Barr, D. S. Wright, W. Clegg, S. M. Hodgson, G. R. Lamming, A. J. Scott, R. E. Mulvey, Angew. Chem. 1989, 101, 1279; Angew. Chem. Int. Ed. Engl. 1989, 28, 1241 (SEDVEC).
42. a) J.-M. Leger, J.-C. Colleter, A. Carpy, Cryst. Struct. Commun. 1982, 11, 1363 (BOTPAB);
43. b) M. Mayer, G. Perez, M. N. Petit, G. Coquerel, Cryst. Struct. Commun. 1992, 11, 1853 (BUHCIQ);
44. c) L. F. Groux, F. Belanger-Gariepy, D. Zargarian, Acta Crystallogr. Sect. C 1999, 55, IUCR9900130 (CARQIV);
45. d) C. van der Brempt, F. Durant, G. Evrard, Bull. Soc. Chim. Belg. 1986, 95, 139 (DIZVUD);
46. e) H.-K. Fun, K. Chinnakali, I. A. Razak, S.-Z. Zhan, C.-J. Hu, Q. Meng, Acta Crystallogr. Sect. C 1999, 55, 766 (HIYDOI);
47. f) G. R. Girard, W. E. Bondinell, L. M. Hillegass, K. G. Holden, R. G. Pendleton, I. Uzinskas, J. Med. Chem. 1989, 32, 1566 (JARSAW);
48. g) V. Kettman, F. Pavelcik, J. Majer, A. Rybar, Acta Crystallogr. Sect C 1989, 45, 282 (KADNIM);
49. h) E. Vazquez, A. Galindo, D. Gnecco, S. Berenes, J. L. Teran, R. G. Enriquez, Tetrahedron: Asymmetry 2001, 12, 3209 (MIXTAO);
50. i) Y. Ishihara, T. Tanaka, W. Miwatashi, A. Fujishima, G. Goto, J. Chem. Soc. Perkin Trans. 1 1994, 2993 (POJVOZ, POJVUF);
51. j) R. J. Hausin, P. W. Codding, J. Med. Chem. 1991, 34, 511 (SIWCAC);
52. k) J. A. Suchocki, E. L. May, T. J. Martin, C. George, B. R. Martin, J. Med. Chem. 1991, 34, 1003 (VIPNIR);
53. l) M. Froimowitz, K.-M. Wu, C. George, A. VanderVeer, Q. Shi, H. M. Deutsch, Struct. Chem. 1998, 9, 295 (WOGPOX);
54. m) J. Buchler, C. Maichle-Mossmer, K.-A. Kovar, Z. Naturforsch. B 2000, 55, 1124 (WOWXIP, WOWXUB);
55. n) K. Ramig, L. Brockunier, P. W. Rafalko, L. A. Rozov, Angew. Chem. 1995, 107, 254; Angew. Chem. Int. Ed. Engl. 1995, 34, 222 (YIJFOM).
56. n) K. Ramig, L. Brockunier, P. W. Rafalko, L. A. Rozov, Angew. Chem. 1995, 107, 254; Angew. Chem. Int. Ed. Engl. 1995, 34, 222 (YIJFOM).
57. a) M. Plamo, M. Klinga, M. Leskela, Z. Kristallogr. 1997, 212, 200 (GEQWUU);
58. b) C. L. Klein, T. A. Banks, D. Rouselle, Acta Crystallogr. Sect C 1991, 47, 1478 (JINGIW);
59. c) D. Carlstrom, Acta Crystallogr. Sect. B 1976, 32, 2460 (MAESCI);
60. d) P. G. Jones, A. K. Fischer, H. Vogt, Z. Kristallogr. 1994, 209, 834 (POSTUM);
61. e) J. Karolak-Wojciechowska, W. Kwiatkowski, S. W. Markowicz, J. Crystallogr. Spectrosc. Res. 1989, 19, 893 (SEFWAB);
62. f) A. Fischer, I. Neda, P. G. Jones, R. Schmutzler, Phosphorus Sulfur Silicon Relat. Elem. 1994, 91, 103 (YUWWIW).
63. 2 net referred to subsequently would be [4.8.8]: see M. O'Keeffe, M. Eddaoudi, H. Li, T. Reineke, O. M. Yaghi, J. Solid State Chem. 2000, 152, 3.
64. N. D. R. Barnett, R. E. Mulvey, W. Clegg, P. A. O'Neil, J. Am. Chem. Soc. 1991, 113, 8187 (KOGYUA).
65. S. C. Nyburg, Acta Crystallogr. Sect. C 1996, 52, 192 (ZIVMUM).
66. J. Weinstock, H.-J. Oh, C. W. De Brosse, D. S. Eggleston, M. Wise, K. E. Flaim, G. W. Gessner, J. L. Sawyer, C. Kaiser, J. Med. Chem. 1987, 30, 1303 (DUTKAE10).
67. M. G. Gardiner, C. L. Raston, Inorg. Chem. 1996, 35, 4047 (TETGOO).
68. + center were excluded from the far more extensive organic sample.
69. T. S. Cameron, H. W. Scheeren, J. Chem. Soc. Chem. Commun. 1977, 939 (HEXAMC).
70. A. R. Kennedy, R. E. Mulvey, A. Robertson, Chem. Commun. 1998, 89 (NECQER).
71. W. Clegg, S. T. Liddle, R. E. Mulvey, A. Robertson, Chem. Commun. 1999, 511 (JUPHAD).
72. G. R. Kowach, C. J. Warren, R. C. Haushalter, F. J. Di Salvo, Inorg. Chem. 1998, 37, 156 (PIXVIB).
73. F. Riviere, S. Ito, M. Yoshifuji, Tetrahedron Lett. 2002, 43, 119 (CACVIM).
74. + (Gaussian-98, B3LYP/6-31 G**) confirm that the most electropositive region in the iminium cation is located in the vicinity of the C atom rather than the N atom.
75. a) J. M. Williams, S. W. Peterson, G. M. Brown, Inorg. Chem. 1968, 7, 2577 (ACNITR20);
76. b) K. Peters, E.-M. Peters, B. Ventzke, A. Hetzheim, Z. Kristallogr. 1999, 214, 169 (JUPJAF);
77. c) J. Galloy, J.-P. Putzeys, G. Germain, J. P. Declercq, M. van Meerssche, Acta Crystallogr. Sect. B 1974, 30, 2460 (CPXMAM);
78. d) C. van der Brempt, G. Evrard, F. Durant, Acta Crystallogr. Sect C 1986, 42, 1206 (DULVIP);
79. e) A. K. Fischer, P. G. Jones, Acta Crystallogr. Sect. E 2002, 58, o218 (FACRUX);
80. f) K. Peters, E.-M. Peters, K. Grunwald, A. Hetzheim, Z. Kristallogr. 1998, 213, 761 (FAGNEG);
81. g) C. Boga, L. Forlani, C. Silvestroni, A. Bonamartini Corradi, P. Sgarabotto, J. Chem. Soc. Perkin. Trans. 1, 1999, 1363 (KIJZAE);
82. h) B. Pniewska, A. Rykowski, W. Pucko, Pol. J. Chem. 1997, 71, 1102 (LEQHAQ);
83. i) W. P. Fehlhammer, F. Schoder, G. Beck, S. Schrolkamp, Z. Anorg. Allg. Chem. 1993, 619, 1171 (YATCAX);
84. j) N. A. Martem'yanova, Y. M. Chunaev, N. M. Przhiyalgovskaya, L. N. Kurkovskaya, O. S. Filipenko, S. M. Aldoshin, Khim. Geterotsikl. Soedin. 1993, 415 (YITCEJ).
85. I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Pearson, R. Taylor, Acta Crystallogr. Sect. B 2002, 58, 389.
86. Microsoft Corporation, EXCEL-97, 1997.