Acid/Base versus Redox Reaction−The Case of Chloranilic Acid and Hydrazine:  A Supramolecular Decision?

The reaction between the oxidative chloranilic acid and the reductive base hydrazine can in principle follow either of two pathways, a redox or a neutralization reaction. We anticipated the redox reaction and were quite surprised to obtain the salt instead. However, after the salt's crystal str...

Full description

Saved in:
Bibliographic Details
Published inCrystal growth & design Vol. 5; no. 5; pp. 1875 - 1879
Main Authors Kühl, Olaf, Goutal, Sigrid
Format Journal Article
LanguageEnglish
Published Washington,DC American Chemical Society 01.09.2005
Subjects
Cross-disciplinary physics: materials science; rheology
Exact sciences and technology
Materials science
Methods of crystal growth; physics of crystal growth
Physics
Crystal growth
Hydrogen bonds
Stacking sequence
Redox reactions
Crystal structure
Online AccessGet full text

Cover

More Information
Summary:The reaction between the oxidative chloranilic acid and the reductive base hydrazine can in principle follow either of two pathways, a redox or a neutralization reaction. We anticipated the redox reaction and were quite surprised to obtain the salt instead. However, after the salt's crystal structure was solved, it was quite obvious that the reaction is supramolecularly controlled by the formation of a three-dimensional charge-assisted hydrogen bond network between the “polymeric” hydrazinium cations and the parallel π−π stacks of chloranilate anions.
ISSN:1528-7483
1528-7505
DOI:10.1021/cg0501581