Carbon versus oxygen nucleophilic selectivity in the reaction of the aryloxide ions, 2,6- and 3,5-di-tert-butylphenoxide, with the 2-((nitro)sub-x-aryl)-4,6-dinitrobenzotriazole 1-oxide series of super-electrophiles: stereoelectronic factors on C-7 Meisenheimer complex formation versus C-1' SNAr displacement

Article Abstract:

Carbon nucleophilic selectivity versus that of oxygen has been considered in the reaction of 2,6- and 3,5-di-tert-butylphenoxide, aryloxide ions with the super electrophiles of the 2-((nitro)sub-x-aryl)-4,6-dinitrobenzotriazole 1-oxide series. Stereoelectronic factors related to C-7 Meisenheimer complex formation have been studied to contrast them to C-1' S-sub-N-Ar displacement. It appears that 2,6-ArO(neg) behaves as a C-nucleophile with O-attack not possible, likely because of the sterically demanding tert-butyl groups on the sides of the O-nucleophilic center.

Nitrobenzenes

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Regioselectivity and stereoelectronic effects in the reactions of the dinitroanline herbicides trifluralin and benefin with nucleophiles

Article Abstract:

Reactions of two compounds in the dinitroaniline herbicide class, N-ethyl-N-n-butyl-2,6-dinitro-4-(trifouoromethyl)aniline(benefin) and N,N-di-n-propyl-2,6-dinitro-4-(trifluoromethyl)aniline (trifluralin), have been studied with 400 MHz 1H NMR spectroscopy. Regioselectivity and stereoelectronic effects were the focus. Also studied was the N-pheynl-2,6-dinitro-4-(trifluoromethyl)aniline analogue with nucleophiles OD(neg) and SO3(2neg). The first reactions with the OD(neg) give Meisenheimer anionic sigma-complexes based on K3TI reaction sequence.

Herbicides, Aniline, Nitrogen compounds, Amides

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alpha-Effect nucleophiles and azide ion: effective charge studies of displacement reactions at esters

Article Abstract:

Effective charge studies of displacement reactions at esters have been made for alpha-effect nucleophiles and azide ion. The alpha effect is thought to be the result of steric and solvation requirements for the reactions. Leffler parameter values for bond fission in the reactions of alpha-nucleophiles with phenyl acetates exhibit no special differences other than those for which the pK sub-a of the nucleophile is responsible.

Solution (Chemistry), Solutions (Chemistry), Azo compounds

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