Binding of Alkali Metal Ions with 1,3,5-Tri(phenyl)benzene and 1,3,5-Tri(naphthyl)benzene: The Effect of Phenyl and Naphthyl Ring Substitution on Cation-π Interactions Revealed by DFT Study
Autor: | Ali Mirchi, Jerzy Leszczynski, Natalia Sizochenko, Tandabany C. Dinadayalane |
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Rok vydání: | 2017 |
Předmět: |
010405 organic chemistry
Stereochemistry Chemistry Metal ions in aqueous solution Binding energy Cation π 010402 general chemistry Ring (chemistry) Alkali metal 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Physical and Theoretical Chemistry Benzene Basis set Naphthalene |
Zdroj: | The journal of physical chemistry. A. 121(46) |
ISSN: | 1520-5215 |
Popis: | The effect of substitution of phenyl and naphthyl rings to benzene was examined to elucidate the cation−π interactions involving alkali metal ions with 1,3,5-tri(phenyl)benzene (TPB) and 1,3,5-tri(naphthyl)benzene (TNB). Benzene, TPB, and four TNB isomers (with ααα, ααβ, αββ, and βββ types of fusion) and their complexes with Li+, Na+, K+, Rb+, and Cs+ were optimized using DFT approach with B3LYP and M06-2X functionals in conjunction with the def2-QZVP basis set. Higher relative stability of β,β,β-TNB over α,α,α-TNB can be attributed to peri repulsion, which is defined as the nonbonding repulsive interaction between substituents in the 1- and the 8-positions on the naphthalene core. Binding energies, distances between ring centroid and the metal ions, and the distance to metal ions from the center of other six-membered rings were compared for all complexes. Our computational study reveals that the binding affinity of alkali metal cations increases significantly with the 1,3,5-trisubstitution of phenyl and ... |
Databáze: | OpenAIRE |
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