The experimental observation of the intramolecular NO₂/CO interaction in solution.
The weak electrostatic interaction between nitro and carbonyl moieties has been observed by means of variable-temperature NMR spectroscopy. Its energetic contribution was evaluated to be about 3 kcal mol(-1) by DFT calculations, and confirmed by the measurement of internal energy barriers to the rotation of suitable nitroaryl rings.
Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale Risorgimento 4, 40136 Bologna (Italy) http://www2.fci.unibo.it/∼mazzand.
Michel
M
Chiarucci
Alessia
A
Ciogli
Michele
M
Mancinelli
Silvia
S
Ranieri
Andrea
A
Mazzanti
atropisomerism; density functional calculations; dynamic NMR spectroscopy; maleimides; weak interactions