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Stiff, and sticky in the right places: The dramatic influence of preorganizing guest binding sites on the hydrogen bond-directed assembly of rotaxanes
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UNSPECIFIED (2001) Stiff, and sticky in the right places: The dramatic influence of preorganizing guest binding sites on the hydrogen bond-directed assembly of rotaxanes. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 123 (25). pp. 5983-5989. ISSN 0002-7863.
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Abstract
Structural rigidity and the preorganization of thread binding sites are shown to have a major influence on template efficiency in the synthesis of hydrogen bond-assembled rotaxanes. Preorganization is so effective, in fact, that with good hydrogen bond accepters (amides) a "world record" yield of 97% for a [2]rotaxane is obtained. The truly remarkable feature of this efficient template, however, is that it allows even poor hydrogen bond accepters testers) to be used to prepare hydrogen bond-assembled rotaxanes, despite the presence of competing hydrogen bonding groups (anions) which bind the key intermediates at least 10000 x more strongly than single. unorganized, ester groups! The structures of the rotaxanes are established unambiguously in solution by H-1 NMR spectroscopy and in the solid state by X-ray crystallography. As a series they provide unique experimental information regarding the nature of amide-ester hydrogen bonding interactions; in particular they suggest that in CDCl3, amide-ester NH . . .O=C hydrogen bonds are similar to1 kcal mol(-1) weaker than the corresponding amide-amide interactions.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | ||||
Publisher: | AMER CHEMICAL SOC | ||||
ISSN: | 0002-7863 | ||||
Official Date: | 27 June 2001 | ||||
Dates: |
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Volume: | 123 | ||||
Number: | 25 | ||||
Number of Pages: | 7 | ||||
Page Range: | pp. 5983-5989 | ||||
Publication Status: | Published |
Data sourced from Thomson Reuters' Web of Knowledge
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