Conformational studies of dibenzo-16-crown-5 lariat ethers

Richard A. Bartsch, Jong Seung Kim, Uriel Olsher, David M. Purkiss

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Abstract

Conformations of sym-(R)(OR')dibenzo-16-crown-5 compounds with R = decyl and R' = H, CH 3, CH 2CO 2H, and CH 2CO 2CH 3, as well as R = alkyl, fluoroalkyl, alkenyl, and alkynyl and R' = CH 2CO 2H, in solution have been probed by NMR spectroscopy. The difference in chemical shifts of the diastereotopic hydrogens for the methylene groups adjacent to the geminally substituted ring carbon is utilized to assess the ease of inversion of the three-carbon bridges. For lariat ethers with R = C 10H 21, the chemical shift difference is much larger when R' = CH 2CO 2H and CH 2CO 2CH 3 than H and CH 3. In non-hydrogen bonding solvents, the chemical shift difference for lariat ethers with R = C 10H 21 is much larger when R' = CH 2CO 2H than CH 2CO 2CH 3 which demonstrates intramolecular hydrogen bonding of the carboxylic acid-containing side arm with a crown ether oxygen.

Original languageEnglish
Pages (from-to)327-331
Number of pages5
JournalSupramolecular Chemistry
Volume6
Issue number3-4
Publication statusPublished - 1996 Dec 1
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Bartsch, R. A., Kim, J. S., Olsher, U., & Purkiss, D. M. (1996). Conformational studies of dibenzo-16-crown-5 lariat ethers. Supramolecular Chemistry, 6(3-4), 327-331.