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Beryllium‐Based Anion Sponges: Close Relatives of Proton Sponges
Author(s) -
Brea Oriana,
Corral Inés,
Mó Otilia,
Yáñez Manuel,
Alkorta Ibon,
Elguero José
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604325
Subject(s) - beryllium , sponge , proton , ion , chemistry , geology , physics , paleontology , organic chemistry , nuclear physics
Through the use of high‐level ab initio and density functional calculations it is shown that 1,8‐diBeX‐naphthalene (X=H, F, Cl, CN, CF 3 , C(CF 3 ) 3 ) derivatives behave as anion sponges, very much as 1,8‐bis(dimethylamino)naphthalene derivatives behave as proton sponges. The electron‐deficient nature of the BeX substituents, which favors strong charge transfer from the anion towards the former, results in anion affinities that are among the largest ones reported for single neutral molecules.