-
2
-
-
0029838574
-
-
(b) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326-1329.
-
(1996)
Angew. Chem., Int. Ed. Engl.
, vol.35
, pp. 1326-1329
-
-
Hamann, B.C.1
Shimizu, K.D.2
Rebek Jr., J.3
-
3
-
-
0029859437
-
-
(c) Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1996, 118, 10002-10003.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 10002-10003
-
-
Castellano, R.K.1
Rudkevich, D.M.2
Rebek Jr., J.3
-
4
-
-
0002395534
-
-
(a) Mogck, O.; Böhmer, V.; Vogt, W. Tetrahedron 1996, 52, 8489-8496.
-
(1996)
Tetrahedron
, vol.52
, pp. 8489-8496
-
-
Mogck, O.1
Böhmer, V.2
Vogt, W.3
-
5
-
-
1542502565
-
-
(b) Mogck, O.; Paulus, E. F.; Böhmer, V.; Thondorf, I.; Vogt, W. J. Chem. Soc., Chem. Commun. 1996, 2533-2534.
-
(1996)
J. Chem. Soc., Chem. Commun.
, pp. 2533-2534
-
-
Mogck, O.1
Paulus, E.F.2
Böhmer, V.3
Thondorf, I.4
Vogt, W.5
-
6
-
-
0030818032
-
-
(c) Mogck, O.; Pons, M.; Böhmer, V.; Vogt, W. J. Am. Chem. Soc. 1997, 119, 5706-5712.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 5706-5712
-
-
Mogck, O.1
Pons, M.2
Böhmer, V.3
Vogt, W.4
-
7
-
-
0038359860
-
Reversible Dimerization of Tetraureas Derived from Calix[4]arenes
-
M. Pons, ed.; NATO ASI Series, Ser. C; Kluwer Academic Publishers: Dordrecht, The Netherlands
-
(d). Böhmer, V.; Mogck, O.; Pons, M.; Paulus, E. F. Reversible Dimerization of Tetraureas Derived From Calix[4]arenes. In NMR in Supramolecular Chemistry; M. Pons, ed.; NATO ASI Series, Ser. C; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; Vol. 526, pp 45-60.
-
(1999)
NMR in Supramolecular Chemistry
, vol.526
, pp. 45-60
-
-
Böhmer, V.1
Mogck, O.2
Pons, M.3
Paulus, E.F.4
-
9
-
-
0030714098
-
-
and references therein
-
(b) Yamamoto, C.; Okamoto, Y.; Schmidt, T.; Jäger, R.; Vögtle, F. J. Am. Chem. Soc. 1997, 119, 10547-10548 and references therein.
-
(1997)
Am. Chem. Soc.
, vol.119
, pp. 10547-10548
-
-
Yamamoto, C.1
Okamoto, Y.2
Schmidt, T.3
Jäger, R.4
Vögtle, F.J.5
-
10
-
-
0001543691
-
-
(a) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671-12672.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 12671-12672
-
-
Castellano, R.K.1
Kim, B.H.2
Rebek Jr., J.3
-
12
-
-
84920344508
-
-
Heterodimerization propensity was found to be solvent-dependent
-
Heterodimerization propensity was found to be solvent-dependent.
-
-
-
-
13
-
-
84920343921
-
-
Statistically, 1:1 combination of homodimers AA and BB gives heterodimers AB and BA, equivalent species, as 50% of the mixture. See ref 2a for details
-
Statistically, 1:1 combination of homodimers AA and BB gives heterodimers AB and BA, equivalent species, as 50% of the mixture. See ref 2a for details.
-
-
-
-
14
-
-
0033535588
-
-
Remote chirality can direct molecular assembly. In hydrogen-bonded assemblies: (a) Prins, L. J.; Huskens, J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 1999, 398, 498-502.
-
(1999)
Nature
, vol.398
, pp. 498-502
-
-
Prins, L.J.1
Huskens, J.2
De Jong, F.3
Timmerman, P.4
Reinhoudt, D.N.5
-
15
-
-
2242419419
-
-
(b) Russell, K. C.; Lehn, J.-M.; Kyritsakas, N.; DeCian, A.; Fischer, J. New J. Chem. 1998, 123-128.
-
(1998)
New J. Chem.
, pp. 123-128
-
-
Russell, K.C.1
Lehn, J.-M.2
Kyritsakas, N.3
DeCian, A.4
Fischer, J.5
-
16
-
-
0000038904
-
-
In polymeric systems and liquid crystals
-
(c) Simanek, E. E.; Qiao, S.; Choi, I. S.; Whitesides, G. M. J. Org. Chem. 1997, 62, 2619-2621. In polymeric systems and liquid crystals:
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2619-2621
-
-
Simanek, E.E.1
Qiao, S.2
Choi, I.S.3
Whitesides, G.M.4
-
17
-
-
0033519678
-
-
(d) Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451.
-
(1999)
Nature
, vol.399
, pp. 449-451
-
-
Yashima, E.1
Maeda, K.2
Okamoto, Y.3
-
18
-
-
0032710679
-
-
(e) Langeveld-Voss, B. M. W.; Waterval, R. J. M.; Janssen, R. A. J.; Meijer, E. W. Macromolecules 1999, 32, 227-230.
-
(1999)
Macromolecules
, vol.32
, pp. 227-230
-
-
Langeveld-Voss, B.M.W.1
Waterval, R.J.M.2
Janssen, R.A.J.3
Meijer, E.W.4
-
19
-
-
0033617546
-
-
(f) Engelkamp, H.; Middelbeek, S.; Nolte, R. J. M. Science 1999, 284, 785-788.
-
(1999)
Science
, vol.284
, pp. 785-788
-
-
Engelkamp, H.1
Middelbeek, S.2
Nolte, R.J.M.3
-
22
-
-
0031887450
-
-
(i) Sommerdijk, N. A. J. M.; Buynsters, P. J. J. A.; Akdemir, H.; Geurts, D. G.; Pistorius, A. M. A.; Feiters, M. C.; Nolle, R. J. M.; Zwanenburg, B. Chem. Eur. J. 1998, 4, 127-136.
-
(1998)
Chem. Eur. J.
, vol.4
, pp. 127-136
-
-
Sommerdijk, N.A.J.M.1
Buynsters, P.J.J.A.2
Akdemir, H.3
Geurts, D.G.4
Pistorius, A.M.A.5
Feiters, M.C.6
Nolle, R.J.M.7
Zwanenburg, B.8
-
23
-
-
17344363900
-
-
(j) Green, M. M.; Zanella, S.; Gu, H.; Sato, T.; Gottarelli, G.; Jha, S. K.; Spada, G. P.; Schoevaars, A. M.; Feringa, B.; Teramoto, A. J. Am. Chem. Soc. 1998, 120, 9810-9817.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 9810-9817
-
-
Green, M.M.1
Zanella, S.2
Gu, H.3
Sato, T.4
Gottarelli, G.5
Jha, S.K.6
Spada, G.P.7
Schoevaars, A.M.8
Feringa, B.9
Teramoto, A.10
-
24
-
-
0032304181
-
-
(k) Mayer, S.; Maxein, G.; Zentel, R. Macromolecules 1998, 31, 8522-8525.
-
(1998)
Macromolecules
, vol.31
, pp. 8522-8525
-
-
Mayer, S.1
Maxein, G.2
Zentel, R.3
-
25
-
-
0032497197
-
-
(l) Gu, H.; Nakamura, Y.; Sato, T.; Teramoto, A.; Green, M. M.; Jha, S. K.; Andreola, C.; Reidy, M. P. Macromolecules 1998, 31, 6362-6368.
-
(1998)
Macromolecules
, vol.31
, pp. 6362-6368
-
-
Gu, H.1
Nakamura, Y.2
Sato, T.3
Teramoto, A.4
Green, M.M.5
Jha, S.K.6
Andreola, C.7
Reidy, M.P.8
-
26
-
-
0030858329
-
-
(m) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 6345-6359
-
-
Yashima, E.1
Matsushima, T.2
Okamoto, Y.3
-
27
-
-
0031573957
-
-
(n) Palmans, A. R. A.; Vekemans, J. A. J. M.; Havinga, E. E.; Meijer, E. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 2648-2651.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 2648-2651
-
-
Palmans, A.R.A.1
Vekemans, J.A.J.M.2
Havinga, E.E.3
Meijer, E.W.4
-
28
-
-
6744266061
-
-
and references therein
-
(o) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860-1866 and references therein.
-
(1995)
Science
, vol.268
, pp. 1860-1866
-
-
Green, M.M.1
Peterson, N.C.2
Sato, T.3
Teramoto, A.4
Cook, R.5
Lifson, S.6
-
29
-
-
0027472038
-
-
(p) Gulik-Krzywicki, T.; Fouquey, C.; Lehn, J.-M. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 163-167.
-
(1993)
Proc. Natl. Acad. Sci. U.S.A.
, vol.90
, pp. 163-167
-
-
Gulik-Krzywicki, T.1
Fouquey, C.2
Lehn, J.-M.3
-
30
-
-
11944254136
-
-
(q) Fouquey, C.; Lehn, J.-M.; Levelut, A.-M. Adv. Mater. 1990, 2, 254-257.
-
(1990)
Adv. Mater.
, vol.2
, pp. 254-257
-
-
Fouquey, C.1
Lehn, J.-M.2
Levelut, A.-M.3
-
31
-
-
0000445676
-
-
Jakobi, R. A.; Böhmer, V.; Grüttner, C.; Kraft, D.; Vogt, W. New J. Chem. 1996, 20, 493-501.
-
(1996)
New J. Chem.
, vol.20
, pp. 493-501
-
-
Jakobi, R.A.1
Böhmer, V.2
Grüttner, C.3
Kraft, D.4
Vogt, W.5
-
32
-
-
33751391068
-
-
Nowick, J. S.; Powell, N. A.; Nguyen, T. M.; Noronha, G. J. Org. Chem. 1992, 57, 7364-7366.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 7364-7366
-
-
Nowick, J.S.1
Powell, N.A.2
Nguyen, T.M.3
Noronha, G.4
-
33
-
-
2742586108
-
-
For calix[4]arenes functionalized with L-alanine units on their upper rims with similar symmetry, see: Sansone, F.; Barboso, S.; Casnati, A.; Fabbi, M.; Pochini, A.; Ugozzoli, F.; Urmaro, R. Eur. J. Org. Chem. 1998, 897-905.
-
(1998)
Eur. J. Org. Chem.
, pp. 897-905
-
-
Sansone, F.1
Barboso, S.2
Casnati, A.3
Fabbi, M.4
Pochini, A.5
Ugozzoli, F.6
Urmaro, R.7
-
34
-
-
84986437005
-
-
Modeling was performed using MacroModel 6.5 and the MMFF force-field: Mohamadi, F.; Richards, N. G. J.; Guidia, W. C.; Liskamp, R.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
-
(1990)
J. Comput. Chem.
, vol.11
, pp. 440-467
-
-
Mohamadi, F.1
Richards, N.G.J.2
Guidia, W.C.3
Liskamp, R.4
Caulfield, C.5
Chang, G.6
Hendrickson, T.7
Still, W.C.8
-
35
-
-
84920361685
-
-
Compounds 3-10 do, however, show at best statistical heterodimerization with the enantiomers of 5 and 6, derived from D-isoleucine and D-valine, respectively
-
Compounds 3-10 do, however, show at best statistical heterodimerization with the enantiomers of 5 and 6, derived from D-isoleucine and D-valine, respectively.
-
-
-
-
36
-
-
84920356004
-
-
CW and CCW refer to the head-to-tail urea directionality when viewed from the narrow rim of the arylurea 1 in the heterodimer. R or S refers to the absolute stereochemistry of the amino acid side chains
-
CW and CCW refer to the head-to-tail urea directionality when viewed from the narrow rim of the arylurea 1 in the heterodimer. R or S refers to the absolute stereochemistry of the amino acid side chains.
-
-
-
-
37
-
-
0033551825
-
-
and references therein
-
Possibly observed here, CH/π interactions can significantly influence molecular conformation: Umezawa, Y.; Tsuboyama, S.; Takahashi, H.; Uzawa, J.; Nishio, M. Tetrahedron 1999, 55, 10047-10056 and references therein.
-
(1999)
Tetrahedron
, vol.55
, pp. 10047-10056
-
-
Umezawa, Y.1
Tsuboyama, S.2
Takahashi, H.3
Uzawa, J.4
Nishio, M.5
-
38
-
-
84920351538
-
-
note
-
6. Upon heating from 295 to 345 K the heterodimer concentration decreases by 20%, and assembly is driven to the homodimeric states, in agreement with entropic arguments, while the selectivity remains essentially unchanged. See the Supporting Information for details.
-
-
-
-
39
-
-
0004007270
-
-
Chapman & Hall: New York
-
Leonard, J.; Lygo, B.; Proctor, G. Advanced Practical Organic Chemistry, 2nd ed.; Chapman & Hall: New York, 1995; p 277.
-
(1995)
Advanced Practical Organic Chemistry, 2nd Ed.
, pp. 277
-
-
Leonard, J.1
Lygo, B.2
Proctor, G.3
-
40
-
-
84920352136
-
-
7 varies from 8.56 ppm for 7 to 8.23 ppm for 10. The distal -NH shifts from 6.90 ppm in 9 to 6.24 ppm in 8
-
7 varies from 8.56 ppm for 7 to 8.23 ppm for 10. The distal -NH shifts from 6.90 ppm in 9 to 6.24 ppm in 8.
-
-
-
-
41
-
-
0031781176
-
-
Essentially identical results were obtained for assembly 1-6 (Supporting Information). For CD in related molecular recognition studies see: (a) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chein. Soc. 1998, 120, 6185-6186.
-
(1998)
J. Am. Chein. Soc.
, vol.120
, pp. 6185-6186
-
-
Huang, X.1
Rickman, B.H.2
Borhan, B.3
Berova, N.4
Nakanishi, K.5
-
42
-
-
0000362651
-
-
(b) Furusho, Y.; Kimura, T.; Mizuno, Y.; Aida, T. J. Am. Chem. Soc. 1997, 119, 5267-5268.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 5267-5268
-
-
Furusho, Y.1
Kimura, T.2
Mizuno, Y.3
Aida, T.4
-
43
-
-
0000708221
-
-
(c) Murakami, Y.; Hayashida, O.; Nagai, Y. J. Am. Chem. Soc. 1994, 116, 2611-2612.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 2611-2612
-
-
Murakami, Y.1
Hayashida, O.2
Nagai, Y.3
-
44
-
-
0000962847
-
-
(d) Kikuchi, Y.; Kobayashi, K.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 1351-1358.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 1351-1358
-
-
Kikuchi, Y.1
Kobayashi, K.2
Aoyama, Y.3
-
45
-
-
0001722787
-
-
(e) Kikuchi, Y.; Tanaka, Y.; Sutarto, S.; Kobayashi, K.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10302-10306.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 10302-10306
-
-
Kikuchi, Y.1
Tanaka, Y.2
Sutarto, S.3
Kobayashi, K.4
Toi, H.5
Aoyama, Y.6
-
47
-
-
84920351580
-
-
The sensitivity of these highly cooperative assemblies to solvents that compete for hydrogen bonds, e.g. methanol, DMSO, and DMF, has been reported. See refs 2 and 4 for details
-
The sensitivity of these highly cooperative assemblies to solvents that compete for hydrogen bonds, e.g. methanol, DMSO, and DMF, has been reported. See refs 2 and 4 for details.
-
-
-
-
48
-
-
0032925548
-
-
For hydrogen bonding-based asymmetric binding by synthetic receptors, see: (a) Dowden, J.; Edwards, P. D.; Flack, S. S.; Kilburn, J. D. Chem. Eur. J. 1999, 5, 79-89.
-
(1999)
Chem. Eur. J.
, vol.5
, pp. 79-89
-
-
Dowden, J.1
Edwards, P.D.2
Flack, S.S.3
Kilburn, J.D.4
-
49
-
-
0346072349
-
-
(b) Lustenberger, P.; Martinborough, E.; Denti, T. M.; Diederich, F. J. Chem. Soc., Perkin Trans. 2 1998, 747-761.
-
(1998)
J. Chem. Soc., Perkin Trans. 2
, pp. 747-761
-
-
Lustenberger, P.1
Martinborough, E.2
Denti, T.M.3
Diederich, F.4
-
50
-
-
0347802782
-
-
and references therein
-
(c) Pieters, R. J.; Cuntze, J.; Bonnet, M.; Diederich, F. J. Chem. Soc., Perkin Trans. 2 1997, 1891-1900 and references therein.
-
(1997)
J. Chem. Soc., Perkin Trans. 2
, pp. 1891-1900
-
-
Pieters, R.J.1
Cuntze, J.2
Bonnet, M.3
Diederich, F.4
-
52
-
-
0343013963
-
-
(e) Webb, T. H.; Súh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554-8555.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 8554-8555
-
-
Webb, T.H.1
Súh, H.2
Wilcox, C.S.3
-
53
-
-
0025118379
-
-
(f) Liu, R.; Sanderson, P. E. J.; Still, W. C. J. Org. Chem. 1990, 55, 5184-5186.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 5184-5186
-
-
Liu, R.1
Sanderson, P.E.J.2
Still, W.C.3
-
54
-
-
0000507166
-
-
(g) Jeong, K. S.; Muehldorf, A. V.; Rebek, J., Jr. J. Am. Chem. Soc., 1990, 112, 6144-6145.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 6144-6145
-
-
Jeong, K.S.1
Muehldorf, A.V.2
Rebek Jr., J.3
-
55
-
-
84920350191
-
-
Reference 18c
-
(h) Reference 18c.
-
-
-
-
56
-
-
0033544412
-
-
For asymmetric binding in molecular assemblies, see: (a) Nuckolls, C.; Hot, F.; Martin, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 10281-10285.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 10281-10285
-
-
Nuckolls, C.1
Hot, F.2
Martin, T.3
Rebek Jr., J.4
-
57
-
-
0032512839
-
-
(b) Rivera, J. M.; Martín, T.; Rebek, J., Jr. Science 1998, 279, 1021-1023.
-
(1998)
Science
, vol.279
, pp. 1021-1023
-
-
Rivera, J.M.1
Martín, T.2
Rebek Jr., J.3
-
58
-
-
0031010130
-
-
(c) Costante-Crassous, J.; Marrone, T. J.; Briggs, J. M.; McCammon, J. A.; Collet, A. J. Am. Chem. Soc. 1997, 119, 3818-3823.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 3818-3823
-
-
Costante-Crassous, J.1
Marrone, T.J.2
Briggs, J.M.3
McCammon, J.A.4
Collet, A.5
-
59
-
-
33845378933
-
-
(d) Canceill, J.; Lacombe, L.; Collet, A. J. Am. Chem. Soc. 1985, 107, 6993-6996.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 6993-6996
-
-
Canceill, J.1
Lacombe, L.2
Collet, A.3
-
60
-
-
84920347305
-
-
The second, bold-faced R or S represents the stereochemistry of the guest
-
The second, bold-faced R or S represents the stereochemistry of the guest.
-
-
-
-
61
-
-
84920346112
-
-
Similar selectivity is also observed in the binding of β-butyrolactone. This guest is not bound in the 1-2 heterodimer
-
Similar selectivity is also observed in the binding of β-butyrolactone. This guest is not bound in the 1-2 heterodimer.
-
-
-
-
62
-
-
84920354766
-
-
Although encapsulated, 3-methylcyclopentanone is a relatively poor guest for assembly 1-2
-
Although encapsulated, 3-methylcyclopentanone is a relatively poor guest for assembly 1-2.
-
-
-
-
63
-
-
84920359740
-
-
See the Supporting Information for details
-
See the Supporting Information for details.
-
-
-
-
64
-
-
0030787521
-
-
(a) Castellano, R. K.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7132-7137.
-
(1997)
Proc. Natl. Acad. Sci. U.S.A.
, vol.94
, pp. 7132-7137
-
-
Castellano, R.K.1
Rudkevich, D.M.2
Rebek Jr., J.3
-
65
-
-
0033520462
-
-
(b) Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2603-2606.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2603-2606
-
-
Castellano, R.K.1
Nuckolls, C.2
Eichhorn, S.H.3
Wood, M.R.4
Lovinger, A.J.5
Rebek Jr., J.6
-
66
-
-
5244370033
-
-
Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
-
(1996)
Organometallics
, vol.15
, pp. 1518-1520
-
-
Pangborn, A.B.1
Giardello, M.A.2
Grubbs, R.H.3
Rosen, R.K.4
Timmers, F.J.5
-
67
-
-
0033583713
-
-
Schalley, C. A.; Castellano, R. K.; Brody, M. S.; Rudkevich, D. M.; Suizdak, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 4568-4579.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 4568-4579
-
-
Schalley, C.A.1
Castellano, R.K.2
Brody, M.S.3
Rudkevich, D.M.4
Suizdak, G.5
Rebek Jr., J.6
|