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The Phthalocrowns: Isoindoline-Crown Ether Macrocycles.
MedLine Citation:
PMID:  23186271     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The reaction of diiminoisoindoline with amine terminated polyethers results in the formation of phthalocrown macrocycles. For n = 1 (where n is the number of ether units), a 2+2 condensation takes place, but for n = 2 and 3, a 1+1 macrocycle formation occurs. The n = 2 phthalocrown is particularly stable due to a strong intramolecular hydrogen bond, but the n = 3 ring hydrolyzes to form a 3-imino-1-oxoisoindoline derivatized crown ether species. For the n = 1 phthalocrown, we observed dynamic behavior in the 1H NMR spectrum, and using VTNMR were able to measure a DeltaG++ = 44.6 kJ/mol for proton exchange.
Authors:
Ingrid-Suzy Tamgho; James T Engle; Christopher John Ziegler
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-28
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-28     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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