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Nucleophilic Substitution in the Nitrocobaltocenium Ion
Author(s) -
WolterSteingrube Anne,
Cordsen Kristine,
Heck Jürgen
Publication year - 2017
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201601537
Subject(s) - chemistry , nucleophilic substitution , nucleophile , hydroxide , substitution reaction , sodium hydroxide , nucleophilic aromatic substitution , alcohol , primary (astronomy) , nuclear magnetic resonance spectroscopy , electrochemistry , inorganic chemistry , nucleophilic addition , sodium , medicinal chemistry , organic chemistry , catalysis , physics , electrode , astronomy
The first results of nucleophilic substitution reactions performed in one step, starting from the nitrocobaltocenium cation, are presented. The nitrocobaltocenium ion reacts with water, alcohols, or primary amines, forming the corresponding monofunctionalized cobaltocenium cations. The substitution occurs with primary amines without further additives, whereas for water and alcohol as nucleophiles, additional strong bases like sodium hydroxide are required. Here, we discuss the synthesis and the role of sodium hydroxide. The new compounds are spectroscopically characterized by IR, 1 H NMR and 13 C NMR spectroscopy, as well as HRMS. The electrochemical behavior of different cobaltocenium salts is reported. Furthermore, molecular structures were obtained from the PF 6 salts of azidocarbonylcobaltocenium, nitrocobaltocenium, and methoxycobaltocenium.