Volume 94 Issue 46 | p. 11 | Concentrates
Issue Date: November 21, 2016

Reaction regioselectivity doesn’t require a transition state

Solvent dynamics are key to preferential nitration of toluene at ortho and para ring positions
Department: Science & Technology
News Channels: JACS In C&EN
Keywords: reaction dynamics, physical chemistry, synthesis, regiochemistry

Toluene nitration by nitronium (NO2+) salts yields curious regioselectivity: Although nitration should occur equally at all positions of the ring because the reaction is highly exothermic and the energy barrier is near zero, only 2% of the products are substituted at the meta position. Of various mechanisms proposed to explain this selectivity, none has proven to be satisfactory. That is because the reaction involves no intermediates and no transition states beyond the initial encounter of . . .

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