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Self-fulfilling cavitands: Packing alkyl chains into small spaces

Academic Article
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Overview

related to degree

  • Purse, Byron, Ph.D. in Chemistry, Scripps Research 2000 - 2005

authors

  • Purse, Byron
  • Rebek Jr., Julius

publication date

  • February 2006

journal

  • Proceedings of the National Academy of Sciences of the United States of America  Journal

abstract

  • The present research was undertaken to determine the conformations of alkyl groups that are forced into small spaces. Unbranched alkyl groups assume fully extended conformations in the free space of solutions, because any bends in the structure create steric clashes between hydrogens along the chain. We synthesized a series of alkyl esters of a carboxylic acid attached to the inner surface of a vase-shaped container structure. The shorter esters (ethyl and propyl) can be accommodated in extended conformations, and even small solvent molecules can share the container's space. Longer (butyl-octyl) esters adopt increasingly coiled conformations that writhe rapidly in the limited space of the cavity. Even longer esters (nonyl and decyl) can be synthesized, but their containers become distorted, and their spectra indicate slowed internal motions of the alkyl groups within the space. In general, alkyl groups are readily contorted when their internal strains are compensated by attraction with the inner surfaces and the proper filling of space.
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Research

keywords

  • coiled conformations
  • self-assembly
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Identity

PubMed Central ID

  • PMC1413836

International Standard Serial Number (ISSN)

  • 0027-8424

Digital Object Identifier (DOI)

  • 10.1073/pnas.0511149103

PubMed ID

  • 16477037
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Additional Document Info

start page

  • 2530

end page

  • 2534

volume

  • 103

issue

  • 8

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