1,4,5,8‐Tetrakis(dimethylamino)naphthalene: Synthesis, Structure, “Proton Sponge” and Electron Donor Properties | Zendy

Barth Thomas | Zendy; Krieger Claus | Zendy; Neugebauer Franz A. | Zendy; Staab Heinz A. | Zendy

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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.

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