Premium
1,4,5,8‐Tetrakis(dimethylamino)naphthalene: Synthesis, Structure, “Proton Sponge” and Electron Donor Properties
Author(s) -
Barth Thomas,
Krieger Claus,
Neugebauer Franz A.,
Staab Heinz A.
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199110281
Subject(s) - chemistry , sponge , proton , hydrogen bond , naphthalene , dimethyl sulfoxide , electron , crystallography , electron donor , sulfoxide , medicinal chemistry , stereochemistry , photochemistry , molecule , organic chemistry , catalysis , physics , botany , quantum mechanics , biology
The “double proton sponge” 1 undergoes diprotonation by strong acids (p K a(1) , = 9.8, p K a(2) = 4.9; dimethyl sulfoxide scale) and is a strong electron donor ( E ox = − 0.501 V; Fc/Fc ⊕ = 0.0 V). X‐ray structure analyses show that the pronounced twisting of 1 around the central C(4a)–C(8 a) bond (1 8.8°) is suppressed by the diprotonation and the accompanying formation of two strong N … H … N hydrogen bonds.