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Fingerprinting the Nature of Anions in Pyrylium Complexes: Dual Binding Mode for Anion–π Interactions
Author(s) -
Franconetti Antonio,
NuñezFranco Reyes,
de Gonzalo Gonzalo,
IglesiasSigüenza Javier,
Álvarez Eleuterio,
CabreraEscribano Francisca
Publication year - 2018
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201700981
Subject(s) - chemistry , non covalent interactions , ion , nuclear magnetic resonance spectroscopy , computational chemistry , halogen , spectroscopy , metathesis , molecule , combinatorial chemistry , stereochemistry , organic chemistry , hydrogen bond , alkyl , physics , quantum mechanics , polymerization , polymer
The interplay between noncovalent interactions that involve oxygenated heteroaromatic rings have been studied for the first time in this work. In particular, we report an advance in knowledge‐based anion–π interactions together with (C−H) + ⋅⋅⋅anion contacts. To understand how the anion modulates these interactions, the synthesis of pyrylium salts with a variety of anions was performed by using an anionic metathesis methodology. The synthesized pyrylium complexes were classified in series, for example, anions derived from halogens, from oxoacids, from p‐block elements, and from transition metals. Crystallographic data, DFT calculations, and NMR spectroscopy methods provided access to an overall insight into the noncovalent behavior of the anion in this kind of system. Based on the DFT calculations and 1 H NMR spectroscopy, pyrylium protons can be used as chemical tags to detect noncovalent interactions in this type of compound.