Secondary dibenzylammonium ion binding by [24]crown-8 and [25]crown-8 macrocycles

Tetrahedron Letters

Volumn 40, Issue 19, 1999, Pages 3661-3664

  Ashton, Peter R ^a   Bartsch, Richard A ^b   Cantrill, Stuart J ^c   Hanes Jr , Robert E ^b   Hickingbottom, Sarah K ^c   Lowe, James N ^c   Preece, Jon A ^a   Stoddart, J Fraser ^c   Talanov, Vladimir S ^b   Wang, Zhen He ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b TEXAS TECH UNIVERSITY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Crown ethers; Pseudorotaxanes; Substituted ammonium ion binding; Supramolecular chemistry

Indexed keywords

CROWN ETHER DERIVATIVE; DIBENZYLAMINE; MACROCYCLIC COMPOUND;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; ION TRANSPORT; MASS SPECTROMETRY; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING;

EID: 0033531989     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00553-5     Document Type: Article

References (25)

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13. 2O) from catechol and 2-(2-(2-chloroethoxy)ethoxy)ethanol and was then subsequently reacted with ethyleneglycol in the presence of NaH in dry THF to afford B24C8 in a 33 % yield.
14. [10] DB24C8 (3) was purchased from the Aldrich Chemical Company and used as received.
15. [11] Brown, G. R.; Foubister, A. J. J. Med. Chem. 1983, 26, 590-592.
16. 3 in refluxing MeCN, afforded the [25]crown-8 derivative 5 in an overall yield of 53 %.
17. 3 in refluxing MeCN afforded 6 in a 53 % yield.
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19. 6, see Ashton, P. R.; Glink, P. T.; Stoddart, J. F.; Tasker, P. A.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 729-736.
20. [16] For leading references on this method, see Adrian, J. C.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 678-680.
21. 3. As the values obtained did not differ significantly, only approximate comparisons can be made between these solvents.
22. 6 dissolved in MeCN, afforded crystalline material suitable for X-ray crystallographic analysis, which revealed the formation of a threaded 1:1 complex.
23. 1H NMR signals. Although there is little difference in complexation strengths between [24]crown-8 hosts incorporating one and two benzo units, as in 2 and 3 respectively, once all eight oxygen atoms 'become' phenolic in nature, i.e., as in host 4, the affinity of the [24]crown-8 framework for secondary dibenzylammonium ions becomes effectively zero.
24. [20] Gokel, G. W. Crown Ethers and Cryptands, Royal Society of Chemistry, Cambridge, 1991.
25. 6.