6533b86ffe1ef96bd12cd175

RESEARCH PRODUCT

Substituent effects on the gas-phase basicities of4-x-acetophanes and 4-x-2,6-dimethylacetophenones: a comparison with solution basicities

Domenico SpinelliGiorgio OcchiucciRenato NotoCarlo Dell'erbaAngelo MugnoliGiovanni PetrilloMarino NoviFernando Sancassan

subject

chemistry.chemical_compoundCrystallographychemistryStereochemistryOrganic ChemistryDrug DiscoverySubstituentProtonationRing (chemistry)BiochemistryGas phase

description

Abstract The behaviour towards gas-phase protonation of a series of 2,6-dimethyl-4-X-acetophenones DM1 exhibits strong similarities with that of the corresponding 4-X-acetophenones 1 . A comparison with previous basicity data in solution and AM1 semiempirical calculations suggest that the X-dependent rotation of the probe group out of the plane of the aromatic ring caused by the two ortho methyls is of minor importance in influencing the substituent effect on the gas-phase basicity of DM1 ; on the contrary, it could heavily affect the solvatability and thus be responsible for the observed behaviour of DM1 in strongly acidic media.

yearjournalcountryeditionlanguage
1997-01-01Tetrahedron
https://doi.org/10.1016/s0040-4020(96)01015-0