New “Proton Sponges”, Part 12. Part 11: H. A. Staab, M. Diehm, C. Krieger, Tetrahedron Lett.1996, 36, 2967-2970.
1,8-Bis(dimethylamino)4,5-dihydroxynaphthalene, a Natural, Intramolecularly Protonated “Proton Sponge” with Zwitterionic Structure†
Article first published online: 22 DEC 2003
Copyright © 1997 by WILEY-VCH Verlag GmbH, Germany
Angewandte Chemie International Edition in English
Volume 36, Issue 17, pages 1884–1886, September 17, 1997
How to Cite
Staab, H. A., Kriege, C., Hieber, G. and Oberdorf, K. (1997), 1,8-Bis(dimethylamino)4,5-dihydroxynaphthalene, a Natural, Intramolecularly Protonated “Proton Sponge” with Zwitterionic Structure. Angew. Chem. Int. Ed. Engl., 36: 1884–1886. doi: 10.1002/anie.199718841
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 25 MAR 1997
- hydrogen bonds;
- naphthalene derivatives;
- proton sponges;
- structure elucidation;
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.