Relationship between Chemical Selectivity and Melting Points of Reacting Molecules

Endo, Tadashi; Takeda, Yoshinori; Orii, Toyohiko; Kuwahara, Akio; Ohta, Makoto; Sakai, Michihiko; Okada, Reiko; Hashimoto, Masao

doi:10.1246/bcsj.53.2687

Cited by 7 publications

(1 citation statement)

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“…Thiol 1 has the same group as cysteine side chain (HSCH 2 )17 and 2 is a derivative of cysteamine (the decarboxylated compound of cysteine) 13. Among the binding sites examined, the above acylurea bond was most suitable for precise and specific molecular recognition; amide bond18 (in 3 and 4 ) was not only unable to recognize the interacting solutes but also insensitive to environmental factors (e.g., temperature and solvent composition) 19. Our results are consistent with the finding by Seeman and co‐workers11 mentioned above.…”

Section: Introductionmentioning

confidence: 99%

Vital significance of addition of “shape similarity” between solutes to shape complementarity for more precise molecular recognition in aqueous binary solvents

Endo

2011

The Chemical Record

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Precise and specific molecular recognition is vital to living systems. Discrimination has mainly been studied by using particular host molecules (e.g., crown ethers, cyclodextrin and urea derivatives). Several studies in various fields have pointed out that the famous "lock-and-key theory" (the concept of shape complementarity) is, at present, insufficient for understanding precise discrimination. This seems to come from the fact that various types of intermolecular interactions are decisive in such discrimination. This Review intends to describe the novel concept that "shape similarity" between interacting solutes should be added to "shape complementarity" for more precise discrimination to be achieved. Further, the role of shape similarity between solvent and solute molecules is also described. In relation to precise molecular recognition, weak interactions, which depend on the three-dimensional shape of substituents (shape-specific weak interactions), are described. Possibility of alterations in solvent structures is discussed in aqueous binary solvents.

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Section: Introductionmentioning

confidence: 99%