Structure, stability and guest affinity of tris(3-ureidobenzyl)amine capsules in solution |
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Authors: | Alajarín Mateo Pastor Aurelia Orenes Raúl-Angel Martínez-Viviente Eloísa Rüegger Heinz Pregosin Paul S |
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Institution: | Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, Murcia-30100, Spain. |
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Abstract: | In non-competitive solvents, the tris(3-ureidobenzyl)amines 1 a-c form dimeric assemblies in which guests such as CH(3)CN, CH(3)NO(2), CH(2)Cl(2), CH(3)I, CH(2)BrCl, CH(2)Br(2), CHCl(3) and C(6)H(6) can be encapsulated. Variable temperature (1)H and (1)H,(1)H-ROESY NMR spectroscopy, as well as pulsed-gradient spin-echo (PGSE) diffusion measurements were used to investigate the encapsulation within 1 a1 a (1 a: tris{3-N'-(4-butylphenyl)ureido]benzyl}amine). Kinetic parameters for the encapsulation of CH(3)NO(2), CH(2)Cl(2) and CH(3)I, both in CDCl(3) and in D(8)]toluene have been obtained by using magnetisation transfer methods. These data are discussed together with the thermodynamic parameters. The affinity between guest and capsule seems to be dictated mainly by the electronic, size and shape complementarity between cavity and guest. A gating mechanism for guest exchange is proposed. |
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Keywords: | diffusion encapsulation hydrogen bonds molecular recognition self‐assembly |
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