Template Effects in the Formation of a Tetramethylene-Bridged Hemicarceplex

Autor:	John C. Sherman, Darren A. Makeiff, and Douglas J. Pope
Rok vydání:	2000
Předmět:	Solvent State model Crystallography Colloid and Surface Chemistry Template Stereochemistry Chemistry Molecule General Chemistry Selectivity Biochemistry Catalysis
Zdroj:	Journal of the American Chemical Society. 122:1337-1342
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja9931628
Popis:	We report a study of the template effect in the formation of tetramethylene-bridged hemicarceplex 7·guest. Two tetrol cavitands were bridged with 1,4-dibromobutane in the presence of suitable template (guest) molecules in N-formylpiperidine as solvent. Selectivity was observed when competing templates were present during the reaction: the relative templating abilities (template ratios) of 30 different guest molecules range by 3600-fold, and manifest a significant preference for para-disubstituted benzenes. Twenty-one of the 30 hemicarceplexes used in this templation study are new. The trend in guest selectivity is markedly different from previous studies in which smaller cavities (e.g., carceplex 2·guest) are formed. In such studies, capsule 3·guest was a good transition state model, whereas this is not the case in the present work.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fbd251a603ab0d9226712f42c9a3cde6 https://doi.org/10.1021/ja9931628 Zobrazit plný text záznamu