Intra- and intermolecular electrostatic interactions and their significance for the structure, acidity, and tautomerization behavior of trinitromethane.
We have addressed several interesting issues related to trinitromethane: the propellerlike arrangement of its nitro groups, its lower-than-predicted (although still high) acidity, its aci tautomerization, and the absence of expected very short C-HO intermolecular bridges in the crystal. A combination of crystallographic and computed data was used in our analysis. The structural features mentioned and the anomalous acidity can be attributed to intra- and/or intermolecular electrostatic interactions. Decomposition via C-NO(2) bond scission may occur before aci tautomerization can take place.
Murray
Jane S
JS
Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA. jsmurray@uno.edu
Lane
Pat
P
Göbel
Michael
M
Klapötke
Thomas M
TM
Politzer
Peter
P