Intra- and intermolecular electrostatic interactions and their significance for the structure, acidity, and tautomerization behavior of trinitromethane

Jane S Murray; Pat Lane; Michael Göbel; Thomas M Klapötke; Peter Politzer

doi:10.1063/1.3082406

Intra- and intermolecular electrostatic interactions and their significance for the structure, acidity, and tautomerization behavior of trinitromethane

J Chem Phys. 2009 Mar 14;130(10):104304. doi: 10.1063/1.3082406.

Authors

Jane S Murray¹, Pat Lane, Michael Göbel, Thomas M Klapötke, Peter Politzer

Affiliation

¹ Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA. jsmurray@uno.edu

PMID: 19292531
DOI: 10.1063/1.3082406

Abstract

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.