6533b7d9fe1ef96bd126c0b2
RESEARCH PRODUCT
Crystal structure and reactivity of 2-chloro-3,5-dinitrothiophene and of 2-phenylsulphonyl-3,5-dinitrothiophene with nucleophiles
Renato NotoAngelo MugnoliGiovanni ConsiglioDomenico Spinellisubject
chemistry.chemical_compoundNucleophileAb initio quantum chemistry methodsNucleophilic aromatic substitutionChemistryOrganic ChemistryThiopheneOrganic chemistryReactivity (chemistry)AromaticityCrystal structureBenzeneMedicinal chemistrydescription
The geometry obtained by a crystal structure determination of the title compounds, as compared with that of the analogous benzene derivatives, along with results of ab initio calculations, is used to interpret the different SNAr reactivities in some thiophene and benzene compounds. The smaller rotation of the nitro groups with respect to the aromatic rings observed in thiophene derivatives should be considered a relevant factor in the higher reactivity in the thiophene series.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1988-01-01 | Journal of Heterocyclic Chemistry |