Premium
Evidence for a π Dimer in the Electrochemical Reduction of 1,3,5‐Trinitrobenzene: A Reversible N 2 ‐Fixation System
Author(s) -
Gallardo Iluminada,
Guirado Gonzalo,
Marquet Jordi,
Vilà Neus
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200602690
Subject(s) - dimer , electrochemistry , chemistry , salt (chemistry) , derivative (finance) , crystallography , crystal structure , reduction (mathematics) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , electrode , mathematics , financial economics , economics , geometry
Electrochemical reduction of 1,3,5‐trinitrobenzene ( 1 ) forms π dimer 2 , which evolves to a more stable σ complex. The crystal structure of the NEt 4 + salt of 2 shows π‐stacked chains of radical anions. Solid 2 or dimeric 2 in solution reacts with N 2 to give a dianion in which an azo group links two 1,3,5‐trinitrobenzene units (see picture). The azo derivative is reversibly electrochemically oxidized to 1 .
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom