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1
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0034696923
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For reviews on capsules, see: a) J. Rebek, Jr., Chem. Commun. 2000, 637-643;
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T. Martin, U. Obst, J. Rebek, Jr., Science 1998, 281, 1842-1845.
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Science
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Martin, T.1
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b) R. M. Grotz-feld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487 489;
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c) J. M. Rivera, T. Martin, J. Rebek, Jr., Science 1998, 279, 1021-1023;
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Science
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Rivera, J.M.1
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d)T. Szabo, B. M. O & Leary, J. Rebek, Jr., Angew. Chem. 1998, 110, 3606-3609;
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Szabo, T.O.1
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e) J. M. Rivera, S. L. Craig, T. Martín, J. Rebek, Jr., Angew. Chem. 2000, 112, 2214-2216.
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Angew. Chem.
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Rivera, J.M.1
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f) B. M. ÓLeary, T. Szabo, N. Svenstrup, C. A. Schalley, A. Lutzen, M. Schafer, J. Re-bek, Jr., J. Am. Chem. Soc. 2001,123, 11519-11533.
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J. Am. Chem. Soc.
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Óleary, B.M.1
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23
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0000836244
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For "cylindrical" capsules, see: T. Heinz, D. M. Rudkevich, J. Rebek, Jr.,Angew. Chem. 1999, 111, 1206-1209;
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Angew. Chem.
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Heinz, T.1
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Angew. Chem. Int. Ed. 1999, 38, 1136-1139.
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Angew. Chem. Int. Ed.
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T. Gerkensmeier, W. Iwanek, C. Agena, R. Fröhlich, S. Kotila, C. Näther, J. Mattay, Eur. J. Org. Chem. 1999, 2257-2262;
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For a selection of references for "tetraurea" dimers, see:a) K. D. Shimizu, J. Rebek, Jr., Proc. Natl. Acad. Sci. USA 1995, 92, 12403-12407;
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O. Mogck, V. Bohmer, W. Vogt, Tetrahedron 1996, 52, 8489-8496;
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Tetrahedron
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34
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0041345747
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The orientation/preorganization of reactive groups attached to the urea residues can be used to synthesize multiple catenanes and rotaxanes: a) M. O. Vysotsky, M. Bolte, I. Thondorf, V. Böhmer, Chem. Eur. J. 2003, 9, 3375-3382;
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b) A. Bogdan, M. O. Vysotsky, T. Ikai, Y. Okamoto, V. Böhmer, Chem. Eur. J. 2004, 10, 3324-3330;
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c) L. Wang, M. O. Vysotsky, A. Bogdan, M. Bolte, V. Böhmer, Science 2004, 304, 1312-1314;
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d) A. Bogdan, Y. Rudzevich, M. O. Vy-sotsky, V. Böhmer, Chem. Commun. 2006, 2941-2952.
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Böhmer, V.4
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38
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77952905538
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For a short discussion of the chirality of such dimers, see reference [11 d]
-
For a short discussion of the chirality of such dimers, see reference [11 d].
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-
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39
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0030818032
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The pattern is more complicated for tetraureas that consist of different phenolic units: O. Mogck, M. Pons, V. Böhmer, W. Vogt, J. Am. Chem. Soc. 1997,119, 5706-5712; see also reference [11 d].
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41
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44249084015
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F. Arnaud-Neu, V. Böhmer, J.-F. Dozol, C. Grüttner, R. A. Jakobi, D. Kraft, O. Mauprivez, H. Rouquette, M. J. Schwing-Weill, N. Simon, W. Vogt, J. Chem. Soc. Perkin Trans. 1996, 1175-1182.
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Mauprivez, O.7
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Schwing-Weill, M.J.9
Simon, N.10
Vogt, W.11
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42
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77952926867
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As the solubility in benzene, toluene, and p-xylene is very low, di-chloromethane and chloroform were used as solvents for the following studies
-
As the solubility in benzene, toluene, and p-xylene is very low, di-chloromethane and chloroform were used as solvents for the following studies.
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45
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34147178116
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They exist, for instance in THF, in contrast to dimeric capsules formed by tetraureas derived from tetraethers, see I. Vatsouro, V. Rudzevich, V. Böhmer, Org. Lett. 2007, 9, 1375-1377.
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Org. Lett.
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Vatsouro, I.1
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Böhmer, V.3
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46
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77952915999
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There are, however, exceptions: aryl-and tosylureas of calix[4]ar-enes form exclusively heterodimers in a 1:1 mixture and tetraureas derived from a rigidified calixarenes do not form heterodimers with those derived from usual tetraethers
-
There are, however, exceptions: aryl-and tosylureas of calix[4]ar-enes form exclusively heterodimers in a 1:1 mixture and tetraureas derived from a rigidified calixarenes do not form heterodimers with those derived from usual tetraethers.
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47
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26844565176
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Such an independent dimerization was also observed in mixtures of tri-urea triphenylmethanes with tetraureas (see: a) Y. Rudzevich, V. Rudzevich, C. Moon, I. Schnell, K. Fischer, V. Böhmer, J. Am. Chem. Soc. 2005,127, 14168-14169;
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Rudzevich, Y.1
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Schnell, I.4
Fischer, K.5
Böhmer, V.6
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48
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14844343123
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b) Y. Rudzevich, V. Rudzevich, D. Schollmeyer, I. Thondorf, V. Böhmer, Org. Lett. 2005, 7, 613-616 ) or tetra-CMPO calix[4]arenes.
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Org. Lett.
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Rudzevich, Y.1
Rudzevich, V.2
Schollmeyer, D.3
Thondorf, I.4
Böhmer, V.5
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50
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77952923700
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A further splitting, most probably owing to the directionality of the urea belt, is neglected here. See reference [11 f]
-
A further splitting, most probably owing to the directionality of the urea belt, is neglected here. See reference [11 f].
-
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51
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77952919856
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note
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Crystal data for dimer 2-(C5H5)2Co+.2:2C80H64N4O12P4S4 (C5H5)2Co-43H6O[C182H162CoN8O28P8S8], M=3472.37, triclinic, space group P-1, a = 19.4261(14) Å, b = 22.0123(18) Å, c = 24.9105(17) Å, α = 82.493(6)̊,β = 84.407(6)̊, γ = 65.265(6)̊, V= 9581.0(12) Å3, T = 173 K, Z = 2, ρcald = 1.204 gcm3, λ(MoKa) = 0.71073 Å, 33693 reflections measured, 33693 unique (Rint=0.0), which were used in all calculations. The structure was solved by direct methods (SHELXS-97) and refined by full-matrix least-squares methods on F2 with 2093 parameters. R1 = 0.1282 (I > 2σ(I)) and wR2 = 0.3190, GOF = 1.217; max/min residual density 1.734/-0.644 e Å-3. CCDC 748328 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data-request/cif
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77952901623
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note
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Crystal data for dimer 3a-Et3NH+-H2O.3a: C84H72N4O12P4.C6H15N.2H2O, M = 1519.9, monoclinic, space group P21/c, a = 20.534(11) Å, b = 36.869(4) Å, c = 27.50(1) Å, β = 131.95(2)̊, V = 15348(9) Å3, T= 193 K, Z=8, ρcald = 1.316gcm-3, λ-(CuKα) = 1.54178 Å, 30336 reflections measured, 28968 unique (Rint= 0.1213), which were used in all calculations. The structure was solved by direct methods (SIR-97) and refined by full-matrix least-squares methods on F2 with 1918 parameters. R1 = 0.1419 (I > 2σ(I)) and wR2= 0.4425, GOF= 0.999; max/min residual density 1.44/-0.50 e Å-3. The hydrogen atom at N3 L could not be detected in different Fourier maps. Additionally, the delocalized hydrogen atoms of the hydroxy groups could not be found and as such, the presence of a positive charge at Et3NH+ could not be conclusively stated. CCDC 750129 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at www.ccdc.cam. ac.uk/data-request/cif.
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S. E. Matthews, M. Saadioui, V. Böhmer, S. Barboso, F. Arnaud-Neu, M.-J. Schwing-Weillet, A. G. Carrera, J.-F. Dozol, J. Prakt. Chem. 1999, 341, 264-273.
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