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RESEARCH PRODUCT
Substituent effects of nitro group in cyclic compounds
Krzysztof EjsmontAnna JezuitaAnna JezuitaHalina Szatylowiczsubject
education.field_of_study010405 organic chemistryPopulationSubstituentMolecular modeling010402 general chemistryCondensed Matter PhysicsRing (chemistry)Resonance (chemistry)01 natural sciencesMedicinal chemistryQuantum chemistry0104 chemical sciencesNitro groupchemistry.chemical_compoundDelocalized electronCharge of the substituent active regionchemistrySigma and pi electron structureSubstituent effectsNitroSubstituent effect stabilization energyPhysical and Theoretical ChemistryeducationInductive effectdescription
AbstractNumerous studies on nitro group properties are associated with its high electron-withdrawing ability, by means of both resonance and inductive effect. The substituent effect of the nitro group may be well described using either traditional substituent constants or characteristics based on quantum chemistry, i.e., cSAR, SESE, and pEDA/sEDA models. Interestingly, the cSAR descriptor allows to describe the electron-attracting properties of the nitro group regardless of the position and the type of system. Analysis of classical and reverse substituent effects of the nitro group in various systems indicates strong pi-electron interactions with electron-donating substituents due to the resonance effect. This significantly affects the pi-electron delocalization of the aromatic ring decreasing the aromatic character, evidenced clearly by HOMA values. Use of the pEDA/sEDA model allows to measure the population of electrons transferred from the ring to the nitro group.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-09-04 | Structural Chemistry |