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

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 - H * * * O intermolecular bridges in the crystal. A c...

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Veröffentlicht in:The Journal of chemical physics 2009-03, Vol.130 (10), p.104304-104304-6
Hauptverfasser: Murray, Jane S., Lane, Pat, Göbel, Michael, Klapötke, Thomas M., Politzer, Peter
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container_end_page 104304-6
container_issue 10
container_start_page 104304
container_title The Journal of chemical physics
container_volume 130
creator Murray, Jane S.
Lane, Pat
Göbel, Michael
Klapötke, Thomas M.
Politzer, Peter
description 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 - H * * * O 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.
doi_str_mv 10.1063/1.3082406
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title Intra- and intermolecular electrostatic interactions and their significance for the structure, acidity, and tautomerization behavior of trinitromethane
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