Crystal structure of 2,4-dinitrophenyl 4-methylbenzenesulfonate: a new polymorph

Abstract

The title compound, C13H10N2O7S, was solved in the ortho­rhom­bic space group Pna21. The aromatic substituents on the sulfonate group are oriented gauche to one another with a C—O—S—C torsion angle of −62.0 (3)°. The supra­molecular features that contribute to the crystal lattice are offset π-π and multiple C—H⋯O inter­actions.

Facile synthesis of arylsulfonates from phenol derivatives and sulfonyl chlorides

“…pathways (notably, C-O bond-cleavage and S-O bond-cleavage) have been reported [27]. To investigate the application of arylsulfonates as electrophilic partners in S N Ar reactions, we decided to take advantage of the potential high reactivity of 2,4-dinitrophenyl 4-methylbenzenesulfonate towards nucleophiles in S N Ar reactions [28]. With the sulfonate in hand, we designed our initial experiment choosing amines with different nucleophilicity in order to investigate the regioselectivity of S N Ar reactions with sulfonates.…”

Crystal structure of phenyl 2,4,5-trichlorobenzenesulfonate

“…The basicity of the amine nucleophile and the electronic nature of the substituent on the sulfonyl moiety are responsible for the difference in regioselectivity. We have synthesized various arene-sulfonate analogues in order to investigate the factors responsible for the competition between C-O and S-O bond fission in the reaction with nitrogen nucleophiles (Atanasova et al, 2015;Cooley et al, 2015).…”