Cooperative effect of a classical and a weak hydrogen bond for the metalInduced construction of a self-assembled β-turn mimic

Chemistry - A European Journal

Volumn 15, Issue 40, 2009, Pages 10405-10422

  Laungani, Andy C ^a   Keller, Manfred ^a   Slattery, John M ^b   Krossing, Ingo ^a   Breit, Bernhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Dimerization; Hydrogen bonds; Molecular recognition; Noncovalent interactions; Selfassembly

Indexed keywords

COOPERATIVE EFFECTS; DFT CALCULATION; GEOMETRIC PARAMETER; HYBRID STRUCTURE; METAL COORDINATION; NMR SPECTROSCOPY; NON-COVALENT INTERACTION; NONCOVALENT INTERACTIONS; OLIGOPEPTIDES; PHOSPHANE LIGANDS; SELF-ASSEMBLED; SELF-ASSEMBLING PROCESS; SHEET STRUCTURE; STACKING INTERACTION; WEAK HYDROGEN BOND; X-RAY CRYSTAL ANALYSIS;

AMINES; AMINO ACIDS; BINDING SITES; DIMERIZATION; HYDROGEN; LIGANDS; MASS SPECTROMETRY; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; SELF ASSEMBLY; SULFUR COMPOUNDS;

HYDROGEN BONDS;

EID: 70350004725     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900662     Document Type: Article

References (231)

1. a) F. Vögtle, Supramolecular Chemistry: Introduction, Teubner, Stuttgart, 1989;
2. b) J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, Wiley-VCH, Weinheim, 1995;
3. c) Supramolecular Chemistry: A Concise Introduction (Eds.: J. W. Steed, J. L. Atwood), Wiley, New York, 2000;
4. d) Principles and Methods in Supramolecular Chemistry (Eds.: H.-J. Schneider, A. K. Yatsimirsky), Wiley, New York, 2000;
5. e) Comprehensive Supramolecular Chemistry, Vol. 1-11 (Eds.: J.-M. Lehn, J.L. Atwood, J.E.D. Davies, D. D. MacNicol, F. Vögtle), Pergamon, Oxford, 1996;
6. f) Templating, SelfAssembly and Self-Organization, Vol. 9 (Eds.: J.-P. Sauvage, M. W. Hosseini), Pergamon, New York, 1996.
7. Nanomaterials: a) C Niemeyer, Angew. Chem. 2001, 113, 4254-4287;
8. Angew. Chem. Int. Ed. 2001, 40, 4128-4158;
9. b) N. C. Seeman, Angew. Chem. 1998, 110, 3408-3428;
10. Angew. Chem. Int. Ed. 1998, 37, 3220-3238;
11. c)F. Fujimura, S. Kimura, Org. Lett. 2007, 9, 793-796, and references therein.
12. Biomacromolecules and functions: R. H. Horton, L. A. Moran, R. S. Ochs, D. J. Rawn, G. K. Scrimgeour, Principles of Biochemistrv, Prentice Hall International Inc., London, 1992.
13. Molecular machines: a) Molecular Devices and Machines (Eds.: V. Balzani, M. Venturi, A. Credi), Wiley-VCH, Weinheim, 2003;
14. b) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530;
15. Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
16. c) C. A. Schalley, A. Lutzen, M. Albrecht, Chem. Eur. J. 2004, 10, 1072-1080.
17. Self-assembly using both coordination chemistry and hydrogen bonding: a) M. Albrecht, Chem. Rev. 2001, 101, 3457-3497;
18. b) B. J. Holliday, C. A. Mirkin, Angew. Chem. 2001, 113, 2076-2097;
19. Angew. Chem. Int. Ed. 2001, 40, 2022-2043;
20. c) A. M. Beatty, Coord. Chem. Rev. 2003, 246, 131-143;
21. d) H. W. Roesky, M. Andruh, Coord. Chem. Rev. 2003, 236, 91-119;
22. e) D. Braga, F. Grepioni, Acc. Chem. Res. 2000, 33, 601-608;
23. f) D. Braga, F. Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1406;
24. g) A. D. Burrows, C.-W. Chan, M. M. Chowdhry, J. E. McGrady, D. M. P. Mingos, Chem. Soc. Rev. 1995, 24, 329-339;
25. h) Y. Sunatsuki, Y. Motoda, N. Matsumoto, Coord. Chem. Rev. 2002, 226, 199-209;
26. i) V. Balamurugan, W. Jacob, J. Mukherjee, R. Mukherjee, CrystEngComm 2004, 6, 396-400;
27. j) K. Biradha, CrystEngComm 2003, 5, 374-384;
28. k) S. Kitagawa, S. Kawata, Coord. Chem. Rev. 2002, 224, 11-34;
29. M. Tadokoro, K. Nakasuji, Coord. Chem. Rev. 2000, 198, 205-218;
30. m) D. Natale, J. C. Mareque-Rivas, Chem. Commun. 2008, 425-437;
31. n) B. Conerney, P. Jensen, P. E. Kruger, B. Moubaraki, K. S. Murray, CrystEngComm 2003, 5, 454-458;
32. o) C. J. Kuehl, F. M. Tabellion, A. M. Arif, P. J. Stang, Organometallics 2001, 20, 1956-1959, and reference [6] therein;
33. p) T. J. Burchell, R. J. Puddephatt, Inorg. Chem. 2005, 44, 3718-3730, and reference [2-4] therein;
34. q) S. L. James, D. M. P. Mingos, X. Xu, A. J. P. White, D. J. Williams, J. Chem. Soc. Dalton Trans. 1998, 1335-1340, and reference [2] therein.
35. DNA-metal base pairs: a) G. H. Clever, C. Kaul, T. Carell, Angew. Chem. 2007, 119, 6340-6350;
36. Angew. Chem. Int. Ed. 2007, 46, 6226-6236;
37. b) S. D. Wettig, D. O. Wood, J. S. Lee, J. Inorg. Biochem. 2003, 94, 94-99;
38. c) J. S. Lee, L.J. P. Latimer, R. S. Reid, Biochem. Cell Biol. 1993, 71, 162-168;
39. d) P. Aich, S. L. Labiuk, L. W. Tari, L. J. T. Delbaere, W. J. Roesler, K. J. Falk, R. P. Steer, J. S. Lee, J. Mol. Biol. 1999, 294, 477-485;
40. e) E. Fusch, B. Lippert, J. Am. Chem. Soc. 1994, 116, 7204-7209;
41. f) R. K. O. Sigel, E. Freisinger, S. Metzger, B. Lippert, J. Am. Chem. Soc. 1998, 120, 12000-12007;
42. g) S. Metzger, B. Lippert, J. Am. Chem. Soc. 1996, 118, 12467-12468;
43. h) O. Krizanovic, M. Sabat, R. B. Pfnür, B. Lippert, J. Am. Chem. Soc. 1993, 115, 5538-5548;
44. i) I. Dieter-Wurm, M. Sabat, B. Lippert, J. Am. Chem. Soc. 1992, 114, 357-359;
45. j) C. Price, B. R. Horrocks, A. Mayeux, M. R. J. Elsegood, W Clegg, A. Houlton, Angew. Chem. 2002, 114, 1089-1091;
46. Angew. Chem. Int. Ed. 2002, 41, 1047-1049.
47. Our group has extensively studied self-assembling, hydrogen-bond donor/acceptor-functionalised ligands for catalysis: a) B. Breit, W. Seiche, J. Am. Chem. Soc. 2003, 125, 6608-6609;
48. b) B. Breit, W. Seiche, Angew. Chem. 2005, 117, 1666-1669;
49. Angew. Chem. Int. Ed. 2005, 44, 1640-1643;
50. c) W. Seiche, A. Schuschkowski, B. Breit, Adv. Synth. Catal. 2005, 347, 1488-1494;
51. d)B. Breit, W. Seiche, Pure Appl. Chem. 2006, 78, 249-256;
52. e)F. Chevallier, B. Breit, Angew. Chem. 2006, 118, 1629-1632;
53. Angew. Chem. Int. Ed. 2006, 45,1599-1602;
54. f) M. Weis, C. Waloch, W. Seiche, B. Breit, J. Am. Chem. Soc. 2006, 128, 4188-4189;
55. g) C. Waloch, J. Wieland, M. Keller, B. Breit, Angew. Chem. 2007, 119, 3097-3099;
56. Angew. Chem. Int. Ed. 2007, 46, 3037-3039;
57. h) M.-N. Birkholz, N. V. Dubrovina, H. Jiao, D. Michalik, J. Holz, R. Paciello, B. Breit, A. Borner, Chem. Eur. J. 2007, 13, 5896-5907;
58. i) M.-N. Birkholz, N. V. Dubrovina, I. A. Shuklov, J. Holz, R. Paciello, C. Waloch, B. Breit, A. Borner, Tetrahedron: Asymmetry 2007, 18, 2055-2060;
59. j) I. Usui, S. Schmidt, M. Keller, B. Breit, Org. Lett. 2008, 10, 1207-1210;
60. k)M. de Greef, B. Breit, Angew. Chem. 2009, 121, 559-562;
61. Angew. Chem. Int. Ed. 2009, 48, 551-554.
62. a) A. C. Laungani, J. M. Slattery, I. Krossing, B. Breit, Chem. Eur. J. 2008, 14, 4488-4502;
63. b) A. C. Laungani, B. Breit, Chem. Commun. 2008, 844-846;
64. c) A. C. Laungani, PhD thesis, University of Freiburg i. Br. (Germany), 2008.
65. For other self-assembled catalysts based on hydrogen bonding, see : a) M. E. Wilson, G. M. Whitesides, J. Am. Chem. Soc. 1978, 100, 306-307;
66. b) M. Skander, N. Humbert, J. Collot, J. Gradinaru, G. Klein, A. Loosli, J. Sauser, A. Zocchi, F. Gillardoni, T. R. Ward, J. Am. Chem. Soc. 2004, 126, 14411-14418;
67. c) M. L. Clarke, J. A. Fuentes, Angew. Chem. 2007, 119, 948-951;
68. Angew. Chem. Int. Ed. 2007, 46, 930-933;
69. d) X.-X. Lu, H.-S. Tang, C.-C. Ko, J. K.-Y. Wong, N. Zhu, V. W.-W. Yam, Chem. Commun. 2005, 1572-1574;
70. e) P. A. Duckmanton, A. J. Blake, J. B. Love, Inorg. Chem. 2005, 44, 7708-7710;
71. f) L. K. Knight, Z. Freixa, P. W. N. M. van Leeuwen, J. N. H. Reek, Organometallics 2006, 25, 954-960;
72. g) A. J. Sandee, A. M. van der Burg, J. N. H. Reek, Chem. Commun. 2007, 864-866;
73. h) R. Chen, R. P. J. Bronger, P. C. J. Kamer, P. W N. M. van Leeuwen, J. N. H. Reek, J. Am. Chem. Soc. 2004, 126, 14557-14566;
74. i) L. Shi, X. Wang, C. A. Sandoval, M. Li, Q. Qi, Z. Li, K. Ding, Angew. Chem. 2006,118, 4214-4218;
75. Angew. Chem. Int. Ed. 2006, 45, 4108-4112;
76. j) B. Schaffner, J. Holz, S. P. Verevkin, A. Borner, Tetrahedron Lett. 2008, 49, 768-771;
77. k) Y. Liu, C. A. Sandoval, Y. Yamaguchi, X. Zhang, Z. Wang, K. Kato, K. Ding, J. Am. Chem. Soc. 2006, 128, 14212-14213;
78. l) R. W. Patureau, M. Kuil, A. J. Sandee, J. N. H. Reek, Angew. Chem. 2008, 120, 3224-3227;
79. Angew. Chem. Int. Ed. 2008, 47, 3180-3183;
80. m)P.-A. R. Breuil, R. W. Patureau, J. N. H. Reek, Angew. Chem. 2009, 121, 2196-2199;
81. Angew. Chem. Int. Ed. 2009, 48, 2162-2165.
82. Hydrogen-bonded networks: a) M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668;
83. b) M. C. T. Fyfe, J. R Stoddart, Acc. Chem. Res. 1997, 30, 393-401;
84. c) J. C. Mac Donald, G. M. Whitesides, Chem. Rev. 1994, 94, 2383-2420;
85. d) C. B. Aakeröy, K. R. Seddon, Chem. Soc. Rev. 1993, 22, 397-408;
86. e) Stimulating Concepts in Chemistry (Eds.: R Vögtle, J. R Stoddart, M. Shibasaki), WileyVCH, Weinheim, 2000;
87. f) L. Brunsveld, B.J. B. Polmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4097;
88. g) D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229-2260;
89. h)R. G. Chapman, J. C Sherman, Tetrahedron 1997, 53, 15911-15945;
90. i) J. Rebek, Jr., Chem. Soc. Rev. 1996, 25, 255-264;
91. j) D. Philp, J. R Stoddart, Angew. Chem. 1996, 108, 1242-1286;
92. Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196;
93. k) G.M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37-44;
94. l) S. Shenhar, V. M. Rotello, Acc. Chem. Res. 2003, 36, 549-561;
95. m) C. J. Kuehl, R. M. Tabellion, A. M. Arif, P. J. Stang, Organometallics 2001, 20, 1956-1959, and reference [4] therein;
96. n) C. B. Aakeröy, A. M. Beatty, D. S. Leinen, Angew. Chem. 1999, 111, 1932-1936;
97. Angew. Chem. Int. Ed. 1999, 38, 1815-1819;
98. o) C. B. Aakeröy, A. M. Beatty, D. S. Leinen, K. R. Lorimer, Chem. Commun. 2000, 935-936;
99. p) C. B. Aakeröy, A. M. Beatty, Chem. Commun. 1998, 1067-1068, and reference [2] therein.
100. Hydrogen-bond donor/acceptor arrays: a) R. P. Sijbesma, E. W. Meijer, Chem. Commun. 2003, 5-16;
101. b) S. C. Zimmerman, P. S. Corbin, Struct. Bonding (Berlin) 2000, 96, 63-94;
102. c) C. Schmuck, W. Wienand, Angew. Chem. 2001, 113, 4493-4499;
103. Angew. Chem. Int. Ed. 2001, 40, 4363-4369;
104. d) B. Gong, Synlett 2001, 582-589;
105. e) P. K. Baruah, R. Gonnade, U. D. Phalgune, G. J. Sanjayan, J. Org. Chem. 2005, 70, 6461-6467, and references 5-7 cited therein;
106. f) J. Zhu, J.-B. Lin, Y.-X. Xu, X.-B. Shao, X.-K. Jiang, Z.-T. Li, J. Am. Chem. Soc. 2006, 128, 12307-12313, and reference [4,5,10] therein;
107. g) Supramolecular Assembly via Hydrogen Bonds (Ed. : D. M. P. Mingos), Springer, Berlin, 2004.
108. Nanopatterns through hydrogen-bond-assisted self-assembly at the solid/liquid interface: C. Meier, U. Ziener, K. Landfester, P. Weihrich, J. Phys. Chem. B 2005, 109, 21015-21027, and refs. [3-25] therein.
109. Self-assembly just by weak hydrogen bonding in the solid state: a) D. S. Reddy, B. S. Goud, K. Panneerselvam, G. R. Desiraju, J. Chem. Soc. Chem. Commun. 1993, 663-664;
110. b) G. Mehta, R. Vidya, J. Org. Chem. 2000, 65, 3497-3502;
111. c) P. W. Baures, J. R. Rush, S. D. Schroeder, A. M. Beatty, Cryst. Growth Des. 2002, 2, 107-110;
112. d) C. Meier, U. Ziener, K. Landfester, P. Weihrich, J. Phys. Chem. B 2005, 109, 21015-21027, and refs. [3-25] therein.
113. Weak hydrogen-bond-directed nanostructures: a) C. L. D. Gibb, E. D. Stevens, B. C Gibb, J. Am. Chem. Soc. 2001, 123, 5849-5850;
114. b) U. Ziener, J.-M. Lehn, A. Mourran, M. Möller, Chem. Eur. J. 2002, 8, 951-957;
115. c) J. V. Barth, J. Weckesser, C. Cai, P. Günter, L. Bürgi, O. Jeandupeux, K. Kern, Angew. Chem. 2000, 112, 1285-1288;
116. Angew. Chem. Int. Ed. 2000, 39, 1230-1234;
117. d) R Vidal, E. Delvigne, S. Stepanow, N. Lin, J. V. Barth, K. Kern, J. Am. Chem. Soc. 2005, 127, 10101-10106;
118. e) P. Zell, R. Mogele, U. Ziener, B. Rieger, Chem. Commun. 2005, 1294-1296.
119. C-H-O hydrogen bonds in A-T and G-C base pairs: a) J. R. Quinn, S. C. Zimmerman, J. E. Del Bene, I. Shavitt, J. Am. Chem. Soc. 2007, 129, 934-941;
120. b) R. K. Castellano, V. Gramlich, R Diederich, Chem. Eur. J. 2002, 8, 118-129;
121. c) C. Ponseca Guerra, R M. Bickelhaupt, Angew. Chem. 2002, 114, 2194-2197;
122. Angew. Chem. Int. Ed. 2002, 41, 2092-2095;
123. d) A. N. Patwa, S. Gupta, R. G. Gonnade, V. A. Kumar, M. M. Bhadbhade, K. N. Ganesh, J. Org. Chem. 2008, 73, 1508-1515.
124. In general, crystal structures can be regarded as " supermolecules", thus leading to many other examples of C-H-X interactions in the solid state, in which these interactions are rather common: G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
125. a) G. A. Jeffrey, W. A. Saenger, Hydrogen Bonding in Biological Structures, Springer, Berlin, 1994;
126. b) R. K. Castellano, Curr. Org. Chem. 2004, 8, 845-865;
127. c) A. C. Pierce, E. ter Haar, H. M. Binch, D. P. Kay, S. R. Patel, P. Li, J. Med. Chem. 2005, 48, 1278-1281;
128. d) S. K. Panigrahi, G. R. Desiraju, J. Biosci. 2007, 32, 677-691;
129. e) A. C. Pierce, K. L. Sandretto, G. W. Bemis, Protein J. 2002, 49, 567-576;
130. f) S. Sarkhel, G. R. Desiraju, Proteins 2004, 54, 247-259;
131. g) L. Jiang, L. H. Lai, J. Biol. Chem. 2002, 277, 37732-37740;
132. h) A. Senes, I. Ubarretxena-Belandia, D. M. Engelman, Proc. Natl. Acad. Sci. USA 2001, 98, 9056-9061;
133. i) B. Loll, G. Raszewski, W. Saenger, J. Biesiadka, J. Mol. Biol. 2003, 328, 131-141;
134. j)M. Mottamal, T. Lazaridis, Biochemistry 2005, 44,1607-1613;
135. k) S. Aravinda, N. Shamala, A. Bandyopadhyay, P. Balaram, J. Am. Chem. Soc. 2003, 125, 15065-15075;
136. l) S. Scheiner, J. Phys. Chem. B 2006, 110, 18670-18679;
137. m) G. R Rabióla, S. Krishnaswamy, V. Nagarajan, V. Pattabhi, Acta Crystallogr. Sect. A 1997, 53, 316-320;
138. n) P. Chakrabarti, S, Chakrabarti, J. Mol. Biol. 1998, 284, 867-873;
139. o) R. Cordier, M. Barfield, S. Grzesiek, J. Am. Chem. Soc. 2003, 125, 15750-15751.
140. a) G. R. Desiraju, Crystal Engineering. The Design of Organic Solids, Elsevier, Amsterdam, 1989;
141. b) D. Braga, R Grepioni, G. R. Desiraju, Chem. Rev. 1998, 98, 1375-1406;
142. c) G. R. Desiraju, Angew. Chem. 1995, 107, 2541-2558;
143. Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327;
144. d) J. D. Dunitz, A. Gavezzotti, Acc. Chem. Res. 1999, 32, 677-684;
145. e) D. Braga, R Grepioni, Acc. Chem. Res. 2000, 33, 601-608.
146. C-H-X interactions in the solution state: a) L. Huggins, J. Org. Chem. 1936, 1, 407-456;
147. b) M.P. Sammes, R. L. Harlow, S. H. Simonsen, J. Chem. Soc. Perkin Trans. 2 1976, 1126-1130;
148. c) P. Jedlovszky, L. Turi, J. Phys. Chem. B 1997, 101, 5429-5436;
149. d) K. Mizuno, T. Ochi, Y. Shindo, J. Chem. Phys. 1998, 109, 9502-9507;
150. e) A. Donati, S. Ristori, C. Bonechi, L. Panza, G. Martini, C. Rossi, J. Am Chem. Soc. 2002, 124, 8778-8779;
151. f) E. S. Alekseyeva, A. S. Batsanov, L. A. Boyd, M. A. Pox, T. G. Hibbert, J. A. K. Howard, J. A. Hugh MacBride, A. Mackinnon, K. Wade, Dalton Trans. 2003, 475-482;
152. g) A. Cappelli, G. Giorgi, M. Anzini, S. Vomero, S. Ristori, C. Rossi, A. Donati, Chem. Eur. J. 2004, 10, 3177-3183;
153. h) J. R. Quinn, S. C. Zimmerman, Org. Lett. 2004, 6, 1649-1652;
154. i) I. El Drubi Vega, P. A. Gale, M. E. Light, S. J. Loeb, Chem. Commun. 2005, 4913-4915;
155. j) Z. Li, J. Ding, G. Robertson, M. Day, Y. Tao, Tetrahedron Lett. 2005, 46, 6499-6502;
156. k) J. L. Russ, J. Gu, K.-H. Tsai, T. Glass, J. C Duchamp, H. C Dorn, J. Am. Chem. Soc. 2007, 129, 7018-7027.
157. Weak hydrogen bonds as structural motifs for a self-assembly process have been noted previously in solid state (see refs. [12,13,17b]), but not in solution or in the context of ligand design (see ref. [17c]).
158. Design of artificial ß-sheets through introduction of structure-directing templates and molecular scaffolds (reviews): a) J. P. Schneider, J. W. Kelly, Chem. Rev. 1995, 95, 2169-2187;
159. b) J. S. Nowick, E. M. Smith, M. Pairish, Chem. Soc. Rev. 1996, 25, 401-415;
160. c) J. Venkatraman, S. C. Shankaramma, P. Balaram, Chem. Rev. 2001, 101, 3131-3152.
161. a) M. Peigel, J. Am. Chem. Soc. 1986, 108, 181-182;
162. b) G. Wagner, M. Feigel, Tetrahedron 1993, 49, 10831-10842;
163. c) H. Diaz, J. W. Kelly, Tetrahedron Lett. 1991, 32, 5725-5728;
164. d) H. Diaz, J. R. Espina, J. W. Kelly, J. Am. Chem. Soc. 1992, 114, 8316-8318;
165. e) H. Diaz, K. Y. Tsang, D. Choo, J. W. Kelly, Tetrahedron 1993, 49, 3533-3545;
166. f) K. Y. Tsang, H. Diaz, N. Graciani, J. W. Kelly, J. Am. Chem. Soc. 1994, 116, 3988-4005;
167. g) C. L. Nesloney, J.W. Kelly, J. Am. Chem. Soc. 1996, 118, 5836-5845.
168. a) J. S. Nowick, N. A. Powell, E. J. Martínez, E. M. Smith, G. Noronha, J. Org. Chem. 1992, 57, 3763-3765;
169. b) J.S. Nowick, E. M. Smith, G. Noronha, J. Org. Chem. 1995, 60, 7386-7387;
170. c) J. S. Nowick, S. Mahrus, E. M. Smith, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 1066-1072;
171. d)J. S. Nowick, S. Insaf, J. Am. Chem. Soc. 1997, 779, 10903-10908.
172. a) D. Ranganathan, V. Haridas, S. Kurur, R. Nagaraj, E. Bikshapathy, A. C. Kunwar, A. V. S. Sarma, M. Vairamani, J. Org. Chem. 2000, 65, 365-374;
173. b) C. P. R. Hackenberger, I. Schiffers, J. Runsink, C. Bolm, J. Org. Chem. 2004, 69, 739-743;
174. c) F. Sansone, L. Baldini, A. Casnati, E. Chierici, G. Faimani, F. Ugozzoli, R. Ungaro, J. Am. Chem. Soc. 2004, 126, 6204-6205;
175. d) A. Aemissegger, V. Kräutler, W. F. van Gunsteren, D. Hilvert, J. Am. Chem. Soc. 2005, 127, 2929-2936;
176. e) A. S. M. Ressurreição, A. Bordessa, M. Civera, L. Belvisi, C. Gennari, U. Piarulli, J. Org. Chem. 2007, 72, 652-660.
177. a) H. Zeng, X. Yang, R. A. Flowers II, B. Gong, J. Am. Chem. Soc. 2002, 124, 2903-2910;
178. b) K. S. Satheeshkumar, G. Vasu, V. Vishalakshi, M. S. Moni, R. Jayakumar, J. Mol. Recognit. 2004, 17, 67-75.
179. Metal-directed ß-sheet self-assembly: a) J. P. Schneider, J. W. Kelly, J. Am. Chem. Soc. 1995, 117, 2533-2546;
180. b) M. Kruppa, C. Bonauer, V. Michlová, B. König, J. Org. Chem. 2005, 70, 5305-5308;
181. c) N. Barooah, R. J. Sarma, J. B. Baruah, Eur. J. Inorg. Chem. 2006, 2942-2946.
182. The dimerisation of polarised DNA double strands by strong divalent metal coordination and only one intermolecular hydrogenbonding interaction has been proposed by Lee and Lippert (see, for example, ref. [6a]). The exact structures of these DNA-metal complexes are, however, still the subject of controversy.
183. Abbreviations used within this paper: A: acceptor; Ac: acetate; Ala: alanine; Bn: benzyl; cod: 1,5-cyclooctadiene; D: donor; DCC: dicyclohexylcarbodiimide; DIC: diisopropylcarbodiimide ; DMAP: dimethylamino-pyridine; Fmoc: 9-fluorenylmethoxycarbonyl; EE: ethyl acetate; PE: petroleum ether (b.p. 40-65°C); Piv: pivaloyl; TFAc: trifluoroacetyl; Val: valine; WHB: weak hydrogen bond; Z: benzyloxycarbonyl.
184. An alternative m-DPPBA synthesis has been reported previously: a) O. Herd, A. Heßler, M. Hingst, M. Tepper, O. Stelzer, J. Organomet. Chem. 1996, 522, 69-76;
185. b) M. Hingst, M. Tepper, O. Stelzer, Eur. J. Inorg. Chem. 1998, 73-82.
186. M. A. Peterson, J. R. Mitchell, J. Org. Chem. 1997, 62, 8237-8239.
187. G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem. 1978, 90, 602-615;
188. Angew. Chem. Int. Ed. Engl. 1978, 17, 569-583.
189. J. R. Pratt, W. D. Massey, R H. Pinkerton, S. R Thames, J. Org. Chem. 1975, 40, 1090-1094.
190. Synthesis of m-DPPA has already been reported: A. Hessler, O. Stelzer, J. Org. Chem. 1997, 62, 2362-2369.
191. 31P NMR Spectroscopy in Stereochemical Analysis, Organic Compounds and Metal Complexes (Eds.: J. G. Verkade, L. D. Louis), VCH, Weinheim, 1987;
192. 13C NMR of Transition Metal Phosphine Complexes: P. S. Pregosin, R. W. Kunz in NMR Basic Principles and Progress, Vol. 16 (Eds.: P. Diehl, E. Fluck, R. Kosfeld), Springer, Heidelberg, 1979, and references therein.
193. In the last 20 years, database mining of the Cambridge Structural Database (CSD) and the Brookhaven Protein Data Bank (PDB) have increasingly been applied to identify and characterise weak intermolecular interactions in chemical and biological systems: a) G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449;
194. b)T. Steiner, Chem. Commun. 1997, 727-734;
195. c) T. Steiner, G. R. Desiraju, Chem. Commun. 1998, 891-892;
196. d) M. Mascai, Chem. Commun. 1998, 303-304;
197. e) T. Steiner, Cryst. Res. Technol. 2003, 9, 177-228;
198. f) R. Taylor, O. Kennard, J. Am. Chem. Soc. 1982, 104, 5063-5070. See also ref. [16].
199. a) S. O. Grim, R. L. Keiter, W. McFarlane, Inorg. Chem. 1967, 6, 1133-1137;
200. b)W. McFarlane, J. Chem. Soc. A 1967, 1922-1923;
201. c) H. G. Alt, R. Baumgärtner, H. A. Brune, Chem. Ber. 1986, 119, 1694-1703.
202. K. S. Satheeshkumar, G. Vasu, V. Vishalakshil, M. S. Moni, R. Jayakumar, J. Mol. Recognit. 2004, 17, 67-75.
203. R. A. Musah, G. M. Jensen, R. J. Rosenfeld, D. E. McRee, D. B. Goodin, J. Am. Chem. Soc. 1997, 119, 9083-9084, and reference [15] therein.
204. R. Taylor, O. Kennard, W. Versichel, Acta Crystallogr. Sect. B 1984, 40, 280-288.
205. H. Adams, R J. Carver, C. A. Hunter, J. C. Morales, E. M. Seward, Angew. Chem. 1996, 108, 1628-1631;
206. Angew. Chem. Int. Ed. Engl. 1996, 35, 1542-1544.
207. A. Allerhand, P. von Ragué, Schleyer, J. Am. Chem. Soc. 1963, 85, 1715-1723;
208. Schleyer, J. Am. Chem. Soc. 1963, 85, 1715-1723.
209. a) J. Gauss, J. Chem. Phys. 1993, 99, 3629-3643;
210. b) J. Gauss, J. R Stanton, J. Chem. Phys. 1995, 102, 251-253;
211. c) K. Wolinski, J. R. Hinton, P. Pulay, J. Am. Chem. Soc. 1990, 112, 8251-8260.
212. a) T. Steiner, Angew. Chem 2002, 114, 50-80;
213. Angew. Chem. Int. Ed. 2002, 41, 48-76;
214. b) J. Rossmeisl, J. K. Nørskov, K. W. Jacobsen, J. Am. Chem. Soc. 2004, 126, 13140-13143.
215. a) SHELXS97, Program for the solution of crystal structures, G. M. Sheldrick, University of Göttingen, Göttingen, 1997;
216. b) SHELXS97, Program for the refinement of crystal structures, G. M. Sheldrick, University of Göttingen, Göttingen, 1997.
217. SHELXTL, The complete software package for single crystal structure determination, release 5.10, G. M. Sheldrick, Bruker AXS, Inc., Madison, 1997.
218. R. Ahlrichs, M. Baer, M. Häser, H. Horn, C. Koelmel, Chem. Phys. Lett. 1989, 762, 165-169.
219. M. von Arnim, R. Ahlrichs, J. Chem. Phys. 1999, 111, 9183-9190.
220. R Weigend, M. Häser, Theo. Chem. Acc. 1997, 97, 331-340.
221. Gaussian 03, Revision B.04, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T Vreven, K.N. Kudin, J. C Burant, J.M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh PA, USA, 2003.
222. a) J. E. Carpenter, R Weinhold, J. Mol. Struct. 1988, 172, 41-62;
223. b) J. E. Carpenter, PhD thesis, University of Wisconsin (USA), 1987;
224. c) J. P. Poster, R Weinhold, J. Am. Chem. Soc. 1980, 102, 7211-7218;
225. d) A. E. Reed, R Weinhold, J. Chem. Phys. 1983, 78, 4066-4073;
226. e) A. E. Reed, R Weinhold, J. Chem. Phys. 1983, 78, 1736-1740;
227. f) A. E. Reed, R. B. Weinstock, R Weinhold, J. Chem. Phys. 1985, 83, 735-746;
228. g) A. E. Reed, L. A. Curtiss, R Weinhold, Chem. Rev. 1988, 88, 899-926;
229. h) F. Weinhold, J. E. Carpenter in The Structure of Small Molecules and Ions (Eds.: R. Naaman, Z. Vager), Plenum, New York, 1988, pp. 227-236.
230. The IGLO-III basis sets for C/H consist of (Ils7p2d/6s2p) primitive sets contracted to [7s6p2d/4s2p]: a) K. L. Schuchardt, B. T. Didier, T. Elsethagen, L. Sun, V. Gurumoorthi, J. Chase, J. Li, T. L. Windus, J. Chem. Inf. Comput. Sci. 2007, 47, 1045-1052;
231. b) W. Kutzelnigg, U. Pleischer, M. Schindler in NMR-Busic Principles and Progress, Vol. 23, Springer, Heidelberg, 1990.