6533b872fe1ef96bd12d3868

RESEARCH PRODUCT

13C-NMR Based Evaluation of the Electronic and Steric Interactions in Aromatic Amines

Anna ZakrzewskaRyszard GawineckiBorys OśmiałowskiErkki Kolehmainen

subject

Steric effectsAmino groups; substituent effects; steric inhibition to resonance; 13C- and 15N-NMR; aromatic aminesStereochemistryaromatic aminesSubstituentsteric inhibition to resonanceMedicinal chemistryCatalysisInorganic Chemistrylcsh:Chemistrychemistry.chemical_compoundGroup (periodic table)AtomElectronic effectReactivity (chemistry)Physical and Theoretical ChemistryMolecular Biologylcsh:QH301-705.5SpectroscopyAmino groupssubstituent effectsChemistryChemical shiftOrganic Chemistry13C- and 15N-NMRGeneral MedicineCarbon-13 NMRComputer Science Applicationslcsh:Biology (General)lcsh:QD1-999

description

Abstract: Chemical shifts of the para carbon atoms, δ(13C-4), in a series of aromatic amines were used to calculate the Ãp, ÃR and ÃOR substituent constants for different amino groups. 1-Pyrrolidino, N,N-di-n-butylamino and N,N-diethylamino groups were found to be the most strong electron-donors. ortho-Substitution decreases the donor properties of the amino group. The amino groups in 2,6-di-i-propylaniline and N,N-2,6-tetramethylaniline have very weak electron-donor properties. The nitrogen atom in benzoquinuclidine and N,N-dimethyl-2,6-di-i-propylaniline have an electron-acceptor character. The calculated substituent constants of the amino groups studied are consistent with the spectral and reactivity data available in literature. Values of δ(15N) cannot be used as a direct measure of electronic effects of the N atom in anilines.

yearjournalcountryeditionlanguage
2005-01-31International Journal of Molecular Sciences
10.3390/i6010052http://www.mdpi.com/1422-0067/6/1/52/