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1,8‐Bis(dimethylamino)4,5‐dihydroxynaphthalene, a Natural, Intramolecularly Protonated “Proton Sponge” with Zwitterionic Structure
Author(s) -
Staab Heinz A.,
Kriege Claus,
Hieber Gisela,
Oberdorf Klaus
Publication year - 1997
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.199718841
Subject(s) - protonation , sponge , crystal (programming language) , molecule , crystallography , crystal structure , chemistry , anisotropy , proton , type (biology) , stereochemistry , physics , geology , organic chemistry , ion , optics , computer science , paleontology , quantum mechanics , programming language
Not the expected structure 1 , but the zweitterionic isomer 2 is found in crystals and solutions of the title compound. Molecules of 2 in the crystal form a type of belt, in which the positive part of the wzeitterion faces the negative part of its neighbor. This belt is coordinated to a corresponding second belt, in which the zwitterions are oriented in the opposite direction. This very interesting crystal packing prompts further studies of anisotropic crystal properties.