Crystal structure of 3,5-dimethylphenyl 2-nitrobenzenesulfonate

Abstract

In the title compound, there are inter­molecular S=O⋯N(nitro) inter­actions, with an O⋯N distance of 2.9840 (18) Å, between inversion-related mol­ecules. The aromatic rings attached to the SO3 group are oriented in a gauche fashion around the ester S—O bond, with a C—S—O—C torsion angle of 84.68 (11)°.

Crystal structure of 2,4-dinitrophenyl 2,4,6-trimethylbenzenesulfonate

“…The two aryl rings of the title compound are oriented gauche to one another with a C7-S1-O1-C1 torsion angle of 73.8(2) °. The O2=S1=O3 and C7-S1-O1 bond angles of 119.19 (12) and 102.13(11)°, respectively, are typical for phenyl arene sulfonates with a gauche conformation around the ester S-O bond. Steric hindrance between ortho substituents of the benzene ring results in a 40.8(3)° perturbation of the nitro group relative to the benzene best plane, allowing the shortest contact of 2.760(3) Å between the oxygen atoms of these groups to be close to the sum of the van der Waals radii.…”

“…While the S-O cleavage is responsible for most of the uses currently seen in the literature, a competitive S-O and C-O bond fission of arylsulfonates, in the presence of a nucleophilic amine, lends credence to a facile synthesis of arylamines and arylsulfonamides, two biologically significant classes of compounds [11]. Previously, our group investigated the structure of two unique arylsulfonates [12,13]. A variety of arylsulfonates have been synthesized to gain further insight into the regioselective factors responsible for the S-O/C-O bond cleavage (Scheme 1).…”

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).…”