Organic ammonium halides as analogues of main-group amide/imide complexes in the solid state: Extension of ring-laddering and ring-stacking principles

Coordination Chemistry Reviews

Volumn 249, Issue 19-20, 2005, Pages 2035-2055

  Bond, Andrew D ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

Amide imide complexes; Ammonium halides; Crystal structures; Ring laddering; Ring stacking

Indexed keywords

EID: 23944474840     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2005.03.018     Document Type: Review

References (135)

1. A.D. Bond, and E.L. Doyle Chem. Commun. 2003 2324 (CSD refcode: BAYXEF)
2. G. Knupp, A.W. Frahm, A. Kirfel, T. Frohlich, and G. Will Acta Cryst. C41 1985 468 (CUGBUB)
3. J. Buchler, C. Maichle-Mossmer, and K.-A. Kovar Z. Naturforsch. B55 2000 1124 (YIQKIS)
4. M. Froimowitz, K.-M. Wu, J. Rodrigo, and C. George J. Comput. Aided Mol. Des. 14 2000 135 (KEQNID)
5. H. Chen, R.A. Bartlett, H.V.R. Dias, M.M. Olmstead, and P.P. Power Inorg. Chem. 30 1991 3390 (VOFTAL, VOFTEP)
6. D. Barr, W. Clegg, R.E. Mulvey, R. Snaith, and K. Wade Chem. Commun. 1986 295 (DIFGUU, DIFHAB)
7. D.R. Armstrong, D. Barr, W. Clegg, R.E. Mulvey, D. Reed, R. Snaith, and K. Wade J. Chem. Soc. Chem. Commun. 1986 869 (DOKBOU)
8. K. Gregory, P. von, R. Schleyer, and R. Snaith Adv. Inorg. Chem. 37 1991 47
9. R.E. Mulvey Chem. Soc. Rev. 20 1991 167
10. R.E. Mulvey Chem. Soc. Rev. 27 1998 339
11. A.D. Bond Chem. Eur. J. 10 2004 1885
12. A.D. Bond Cryst. Growth. Des. 5 2005 755
13. J. Koorts, and M. Caira Acta Cryst. C41 1985 552 (CUNVUC)
14. B. Nilsson Acta Cryst. B24 1968 252 (HALOXN)
15. D. Mondeshka, I. Angelova, B. Stensland, P.-E. Werner, and C. Ivanov Acta Chem. Scand. 46 1992 54 (PEFCUY)
16. M. Mayer, G. Perez, M.N. Petit, and G. Coquerel Cryst. Struct. Commun. 11 1982 1853 (BUHCIQ)
17. M. Jaeger, W. Steglich, K. Polborn, Private Communication to the CCDC (2003) (HABXAK).
18. F. Belanger-Gariepy, F. Brisse, P.D. Harvey, I.S. Butler, and D.F.R. Gilson Acta Cryst. C43 1987 756 (FINVAZ)
19. A. Dalpiaz, V. Ferretti, P. Gilli, and V. Bertolasi Acta Cryst. B52 1996 509 (HIJDEJ)
20. N. Sakabe, K. Sakabe, K. Ozeki-Minakata, and J. Tanaka Acta Cryst. B28 1972 3441 (MOATPB10)
21. B.E. Maryanoff, D.F. McComsey, R.R. Inners, M.S. Mutter, G.P. Wooden, S.L. Mayo, and R.A. Olofson J. Am. Chem. Soc. 111 1989 2487 (VALJOH)
22. R. Glaser, D. Shiftan, and M. Drouin New J. Chem. 18 1994 973 (POLCEY)
23. A. Schouten, J.A. Kanters, J. Kroon, R. Plate, and J. Kelder Acta Cryst. C50 1994 128 (LEBHAB)
24. 3 nets referred to subsequently would be [4.8.8] and [6.6.6], respectively
25. D. Carlstrom Acta Cryst. B32 1976 2460 (MAESCI)
26. A. Fischer, I. Neda, P.G. Jones, and R. Schmutzler Phosphorus Sulfur Silicon Relat. Elem. 91 1994 103 (YUWWIW)
27. J. Karolak-Wojciechowska, W. Kwiatkowski, and S.W. Markowicz J. Crystallogr. Spectrosc. Res. 19 1989 893 (SEFWAB)
28. R. Glaser, D. Shiftan, and M. Drouin New J. Chem. 18 1994 973 (POLCIC)
29. C. Follet-Houttemane, J.P. Wignacourt, J.C. Boivin, I. Lesieur, and D. Lesieur Acta Cryst. C47 1991 602 (SITJAG)
30. W.I.F. David, K. Shankland, and N. Shankland Chem. Commun. 1998 931 (PROMZC01)
31. A.V.A. Pinto, I. Vencato, H.A. Gallardo, and Y.P. Mascarenhas Mol. Cryst. Liq. Cryst. 149 1987 29 (DEAMMC02, ZZZLWK02)
32. B.-M. Lunden Acta Cryst. B30 1974 1756 (DODAMB)
33. G. Klebe, V.G. Krishnan, A. Weiss, and H. Fuess Eur. Cryst. Meeting 8 1983 245 (DOMBOW01)
34. J.C. Barnes, J.D. Paton, D. Rae, J. Cairns, and J. Redpath Acta Cryst. C50 1994 728 (HECBEW)
35. J. Gray, and P.G. Jones Z. Naturforsch. B 57 2002 61 (EDUGUF, UFAJAM)
36. K.N. Trueblood Acta Cryst. C43 1987 711 (FINVED)
37. A. Galindo, L. Orea, F.D. Gnecco, R.G. Enriquez, R.A. Toscano, and W.F. Reynolds Tetrahedron Asym. 8 1997 2877 (PUDKUU)
38. C.H. Gorbitz Acta Chem. Scand. 43 1989 871 (VEDCOW)
39. M. Dobler, and J.D. Dunitz Helv. Chim. Acta 47 1964 695 (AZNONB)
40. J. Buchler, C. Maichle-Mossmer, and K.-A. Kovar Z. Naturforsch. B 55 2000 1124 (WOWXOV). In the published atomic coordinates, atoms N2 (a primary ammonium group) and C20 (a methyl group) are interchanged
41. E.F. Paulus, A. Burgard, H.-J. Lang, and U. Gerlach Z. Kristallogr. New Cryst. Struct. 216 2001 663 (ADOLIO)
42. K. Frydenvang, L.M. Hansen, and B. Jensen Acta Cryst. C51 1995 2053 (ZENJAD)
43. Y. Ishihara, T. Tanaka, W. Miwatashi, A. Fujishima, and G. Goto Perkin Trans. 1 1994 2993 (POJVUF)
44. J. Weinstock, H.-J. Oh, C.W. De Brosse, D.S. Eggleston, M. Wise, K.E. Flaim, G.W. Gessner, J.L. Sawyer, and C. Kaiser J. Med. Chem. 30 1987 1303 (DUTKAE10)
45. J.K. Dattagupta, and N.N. Saha Acta Cryst. B29 1973 1228 (MABZAL10)
46. F.H. Allen Acta Cryst. B58 2002 380 CSD Version 5.25 (November 2004) plus January and April 2004 updates
47. W. Uhl, J. Molter, and B. Neumuller J. Organomet. Chem. 634 2001 193 (CAFPEF)
48. S. Kuhner, R. Kuhnle, H.-D. Hausen, and J. Weidlein Z. Anorg. Allg. Chem. 623 1997 25 (RASDUK)
49. H.-D. Hausen, R. Kuhnle, and J. Weidlein Z. Naturforsch B. 50 1995 1419 (ZEVHAJ)
50. G.H. Robinson, F. Moise, W.T. Pennington, and S.A. Sangokoya Polyhedron 8 1989 1279 (JEZGOK)
51. R.E. Allan, M.A. Beswick, A.J. Edwards, M.A. Paver, M.-A. Rennie, P.R. Raithby, and D.S. Wright Dalton Trans. 1995 1991 (ZAQHEE)
52. R.E. Allan, M.A. Beswick, M.K. Davies, P.R. Raithby, A. Steiner, and D.S. Wright J. Organomet. Chem. 550 1998 71 (POYFUE)
53. A. Shimada, Y. Okaya, and M. Nakamura Acta Cryst. 8 1955 819 (CYHACL)
54. A. Downard, and T. Chivers Eur. J. Inorg. Chem. 2001 2193
55. M. Veith, and O. Rectenwald Z. Naturforsch B 38 1983 1054 (CAMPOV)
56. R.E. Allan, D.S. Wright, A. Steiner, P.R. Raithby, J.E. Davies, Private communication to the CCDC (1996) (NABNEJ).
57. C.J. Harlan, S.G. Bott, and A.R. Barron Dalton Trans. 1997 637 (RIMMOP, RIMNAC, RIMMUV)
58. T. Grabowy, and K. Merzweiler Z. Anorg. Allg. Chem. 626 2000 736 (MECKIO, MECKOU, MECKUA)
59. K. Schmid, S. Kuhner, H.-D. Hausen, and J. Weidlein Z. Anorg. Allg. Chem. 623 1997 1499 (RORNUH)
60. F. Cordeddu, H.-D. Hausen, and J. Weidlein Z. Anorg. Allg. Chem. 622 1996 573 (ZOYSAH)
61. G. del Piero, M. Cesari, S. Cucinella, and A. Mazzei J. Organomet. Chem. 137 1977 265 (BALCAT)
62. M. Shabazi, S. Dou, and A. Weiss Z. Naturforsch. A 47 1992 171 (JORXIX)
63. G. Herrschaft, and H. Hartl Acta Cryst. C45 1989 1021 (JAPLAN)
64. E. Lopez-Dupla, P.G. Jones, and F. Vancea Z. Naturforsch. B58 2003 191 (ANLINC01)
65. G. Fecher, A. Weiss, W. Joswig, and H. Fuess Z. Naturforsch. A36 1981 956 (ANLINB03)
66. G. Fecher, and A. Weiss Ber. Bunsenges. Phys. Chem. 90 1986 1 (DOVVIT, DOVVIT01 (deuterated), DOVVIT02 (deuterated))
67. T. Sakai, and H. Terauchi Acta Cryst. B37 1981 2101 (ANLINB02)
68. W.J. Grigsby, T. Hascall, J.J. Ellison, M.M. Olmstead, and P.P. Power Inorg. Chem. 35 1996 3254 (TAVZOF)
69. A.-A.I. Al-Wassil, P.B. Hitchcock, S. Sarisaban, J.D. Smith, and C.L. Wilson Dalton Trans. 1985 1929 (DAYRUQ)
70. C. Schnitter, S.D. Waezsada, H.W. Roesky, M. Teichert, I. Uson, and E. Parisini Organometallics 16 1997 1197 (ROMJIM, ROMJOS, ROMJUY)
71. G. Klebe, V.G. Krishnan, A. Weiss, and H. Fuess Eur. Cryst. Meeting 8 1983 245 (DOMBOW, DOMBOW01, DOMBUC)
72. M. Colapietro, A. Domenicano, C. Marciante, and G. Portalone Acta Cryst. B37 1981 387 (ANLCLA)
73. K.F. Tesh, T.P. Hanusa, and J.C. Huffman Inorg. Chem. 29 1990 1584 (VETFOP)
74. S. Neander, and U. Behrens Z. Anorg. Allg. Chem. 625 1999 1429 (CORVUA, CORWAH, CORXEM)
75. F. Antolini, P.B. Hitchcock, A.V. Khvostov, and M.F. Lappert Eur. J. Inorg. Chem. 2003 3391 (OLEWOR, OLEWUX, OLEXAE)
76. K. Junge, E. Popowski, R. Kempe, and W. Baumann Z. Anorg. Allg. Chem. 624 1998 1369 (GEQSEA, GEQRUP, GEQSAW)
77. P.B. Hitchcock, M.F. Lappert, and D.-S. Liu Chem. Commun. 1994 2637 (POPYOI)
78. D.K. Kennepohl, S. Brooker, G.M. Sheldrick, and H.W. Roesky Chem. Ber. 124 1991 2223 (SOLXUM)
79. S. Daniele, P.B. Hitchcock, M.F. Lappert, T.A. Nile, and C.M. Zdanski Dalton Trans. 2002 3980 (IHEXEY)
80. D.R. Armstrong, K.W. Henderson, A.R. Kennedy, W.J. Kerr, F.S. Mair, J.H. Moir, P.H. Moran, and R. Snaith Dalton Trans. 1999 4063 (CISQAW, CISPEZ)
81. R.B. Wanat, D.B. Collum, G. van Duyne, J. Clardy, and R.T. DePue J. Am. Chem. Soc. 108 1986 3415 (DOZHEF)
82. W. Clegg, S.T. Liddle, K.W. Henderson, F.E. Keenan, A.R. Kennedy, A.E. McKeown, and R.E. Mulvey J. Organomet. Chem. 572 1999 283 (HOLSUW)
83. A. Furstner, C. Mathes, and C.W. Lehmann Chem. Eur. J. 7 2001 5299 (IDOQIB)
84. A.J. Edwards, S. Hockey, F.S. Mair, P.R. Raithby, and R. Snaith J. Org. Chem. 58 1993 6942 (TOMXEY)
85. W. Clegg, L. Horsburgh, S.A. Couper, and R.E. Mulvey Acta Cryst. C55 1999 867 (FIWBAO)
86. M.P. Bernstein, F.E. Romesberg, D.J. Fuller, A.T. Harrison, D.B. Collum, Q.-Y. Liu, and P.G. Williard J. Am. Chem. Soc. 114 1992 5100 (KUFFEW)
87. J.P. Bezombes, P.B. Hitchcock, M.F. Lappert, and P.G. Merle Dalton Trans. 2001 816 (XENYEU)
88. P.C. Andrews, D.R. Armstrong, D.R. Baker, R.E. Mulvey, W. Clegg, L. Horsburgh, P.A. O'Neil, and D. Reed Organometallics 14 1995 427 (YIXYOT)
89. U. Dumichen, T. Gelbrich, and J. Sieler Z. Anorg. Allg. Chem. 625 1999 262 (GILPIA, GILQAT)
90. D.C. Bradley, I.S. Harding, I.A. Maia, and M. Motevalli Dalton Trans. 1997 2969 (PULMOY)
91. E.K. Styron, C.H. Lake, S.J. Schauer, C.L. Watkins, and L.K. Krannich Polyhedron 18 1999 1595 (WIRNAM, WIRNEQ)
92. D.L. Freeman, J.D. Odom, W.R. Nutt, and L. Lebioda Inorg. Chem. 36 1997 2718 (RURSEC)
93. A. Ahmed, W. Schwarz, and H. Hess Z. Naturforsch. B33 1978 43 (BRMAAL)
94. D. Barr, W. Clegg, R.E. Mulvey, and R. Snaith Chem. Commun. 1984 285 (ZEGNII)
95. S.R. Dubberley, P. Mountford, and N. Adams Acta Cryst. E58 2002 m342 (LOXZAZ)
96. K. Ouzounis, H. Riffel, H. Hess, U. Kohler, and J. Weidlein Z. Anorg. Allg. Chem. 504 1983 67 (CASNEP)
97. W. Harrison, A. Storr, and J. Trotter Dalton Trans. 1972 1553 (AZGALT)
98. C.Y. Tang, R.A. Coxall, A.J. Downs, T.M. Greene, and S. Parsons Dalton Trans. 2001 2141 (XICKOJ)
99. L.M. Trefonas, F.S. Matthews, and W.N. Lipscomb Acta Cryst. 14 1961 273 (DMABTR)
100. J.L. Atwood, and G. Stucky J. Am. Chem. Soc. 92 1970 285 (EIMEAL)
101. D.R. Armstrong, D. Barr, W. Clegg, S.M. Hodgson, R.E. Mulvey, D. Reed, R. Snaith, and D.S. Wright J. Am. Chem. Soc. 111 1989 4719 (DOKBOU10, KARTOM)
102. M.G. Gardiner, and C.L. Raston Inorg. Chem. 35 1996 4047 (TETGOO, TETGUU, TETHAB)
103. K.W. Henderson, and P.G. Williard Organometallics 18 1999 5620 (XEWFEK, XEWFIO)
104. M. Vestergren, J. Eriksson, G. Hilmersson, and M. Hakansson J. Organomet. Chem. 682 2003 172 (ENAWUL)
105. D.R. Baker, R.E. Mulvey, W. Clegg, and P.A. O'Neil J. Am. Chem. Soc. 115 1993 6472 (WASWOC)
106. G. Boche, I. Langlotz, M. Marsch, K. Harms, and N.E.S. Nudelman Angew. Chem. Int. Ed. 31 1992 1205 (KUPSET)
107. A.R. Kennedy, R.E. Mulvey, and A. Robertson Chem. Commun. 1998 89 (NECQER)
108. W. Clegg, S.T. Liddle, R.E. Mulvey, and A. Robertson Chem. Commun. 1999 511 (JUPHAD)
109. G.R. Kowach, C.J. Warren, R.C. Haushalter, and F.J. DiSalvo Inorg. Chem. 37 1998 156 (PIXVIB)
110. W. Clegg, K.W. Henderson, L. Horsburgh, F.M. Mackenzie, and R.E. Mulvey Chem. Eur. J. 4 1998 53 (NEXKOQ)
111. F. Riviere, S. Ito, and M. Yoshifuji Tetrahedron Lett. 43 2002 119 (CACVIM)
112. H. Chen, R.A. Bartlett, H.V.R. Dias, M.M. Olmstead, and P.P. Power Inorg. Chem. 30 1991 2487 (JIRTUZ)
113. M.G. Gardiner, and C.L. Raston Inorg. Chem. 34 1995 4206 (ZAXKUE)
114. N.P. Lorenzen, J. Kopf, F. Olbrich, U. Schumann, and E. Weiss Angew. Chem. Int. Ed. 29 1990 1441 (KIJFUE)
115. D. Barr, W. Clegg, S.M. Hodgson, G.R. Lamming, R.E. Mulvey, A.J. Scott, R. Snaith, and D.S. Wright Angew. Chem. Int. Ed. 28 1989 1241 (SEDVEC)
116. L.H. Gade, and N. Mahr Dalton Trans. 1993 489 (PEBJAH)
117. J. Jubb, P. Berno, S. Hao, and S. Gamarotta Inorg. Chem. 34 1995 3563 (ZALCUK)
118. M.F. Lappert, M.J. Slade, A. Singh, J.L. Atwood, R.D. Rogers, and R. Shakir J. Am. Chem. Soc. 105 1983 302 (BUXNUD)
119. P.G. Williard, and Q.-Y. Liu J. Am. Chem. Soc. 115 1993 3380 (YAPCOH)
120. B. Gehrhus, P.B. Hitchcock, A.R. Kennedy, M.F. Lappert, R.E. Mulvey, and P.J.A. Rodger J. Organomet. Chem. 587 1999 88 (KENXOQ)
121. S.W. Ng Acta Cryst. C51 1995 2149 (ZENSUG)
122. R.W. Kaplan, and M.M. Turnbull Acta Cryst. C52 1996 2049 (TEHDEP)
123. M.D. Walkinshaw, A.H. Cowley, and S.K. Mehrotra Acta Cryst. C40 1984 129 (CEFGEZ)
124. B. Rees, and R. Weiss Acta Cryst. B27 1971 932 (TMPIPO)
125. K.H. Claus, and C. Kruger Acta Cryst. C44 1988 1632 (ZZZSAE01)
126. T.S. Cameron, and H.W. Scheeren Chem. Commun. 1977 939 (HEXAMC)
127. M. Polamo, M. Klinga, and M. Leskela Z. Kristallogr. 212 1997 200 (GEQWUU)
128. T. Steiner Angew. Chem. Int. Ed. 41 2002 48
129. P. Jutzi, B. Neumann, G. Reumann, and H.-G. Stammler Organometallics 18 1999 2037 (BIJBEB)
130. R.J. Wehmschulte, and P.P. Power Inorg. Chem. 37 1998 6906 (HIZKUW)
131. S. Schultz, A. Voigt, H.W. Roesky, L. Haming, and R. Herbst-Irmer Organometallics 15 1996 5252 (RARVOV)
132. S. Schultz, L. Haming, R. Herbst-Irmer, H.W. Roesky, and G.M. Sheldrick Angew. Chem. Int. Ed. Engl. 33 1994 969 (SUMRIB)
133. R.J. Wehmschulte, and P.P. Power J. Am. Chem. Soc. 118 1996 791 (ZOPLEV)
134. N.N. Greenwood, and A. Earnshaw Chemistry of the Elements first ed. 1984 Pergamon Press Oxford p. 440
135. M. Froimowitz, and C. George J. Chem. Inf. Comput. Sci. 38 1998 506 (NUFSOW)