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Selenacalix[3]triazines: Anion Versus Proton Association
Author(s) -
Van Rossom Wim,
Thomas Joice,
Terentyeva Tatyana G.,
Maes Wouter,
Dehaen Wim
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201548
Subject(s) - chemistry , lone pair , titration , triazine , ion , proton , crystallography , stereochemistry , non covalent interactions , computational chemistry , inorganic chemistry , molecule , polymer chemistry , hydrogen bond , organic chemistry , physics , quantum mechanics
Selenacalix[3]triazines, cyclotrimeric metacyclophanes with direct Se linkages between the heteroaryl constituents, were shown to associate with various guest species. The preorganization of three electron deficient triazine rings allows for anions to bind through anion‐π interactions, and alignment of the central nitrogen lone pairs and the well‐defined size of the macroring enable association with a single proton. Extended UV/Vis titration studies indicated a clear difference in complexation behavior depending on the outer‐rim substitution pattern. The host–guest properties of analogous selena‐ and thiacalix[3]triazines were found to be notably different.