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Beilstein J. Org. Chem. 2010, 6, No. 3, doi:10.3762/bjoc.6.3
Graphical Abstract
Figure 1: Self-assembly of zwitterion 1 to give dimer 1·1 and self-assembly of zwitterion 2 to give dimer 2·2...
Scheme 1: Synthesis of zwitterion 2.
Scheme 2: Synthesis of compound 2·H+.
Figure 2: 1H NMR spectra of zwitterion 2 (bottom) and its protonated form 2·H+ (top).
Figure 3: Part of the 1H NMR spectrum of 2 in [D6]DMSO showing the complexation-induced shifts of the indole ...
Figure 4: Representative binding isotherm of the aromatic proton d (left) and the indole NH proton (right).
Figure 5: Binding isotherm of the guanidinium NH2 protons.
Figure 6: Crystal structure of dimer 2·2 with hydrogen bond distances (Å) and dihedral angles.
Figure 7: Side view of dimer 2·2 in the solid state.
Figure 8: Part of the crystal lattice of zwitterion 2.
Scheme 3: An attractive H-bond in 1 (left) is replaced by a repulsive steric interaction in 2 (right).
Figure 9: Energy-minimized structure for dimer 2·2 with hydrogen bond distances (Å) and dihedral angles.