Nitrogen lone pair interactions in organic molecules: a photoelectron spectroscopic study.
The electronic structure of several cyclic, saturated and unsaturated amines and imines has been investigated by UV photoelectron spectroscopy (UPS). The analysis of spectra has been performed with DFT and OVGF calculations and comparison with the UPS spectra of related compounds. The extent and type of nitrogen lone pair interactions is discussed because nitrogen lone pairs are the most important functional groups present in these molecules. The magnitude of interactions was found to depend on the spatial orientation and rigidity of mutual positions of the lone pairs, rather than on their spatial distance.
Novak
Igor
I
Department of Chemistry, National University of Singapore, Singapore 117543, Singapore. chmigorn@nus.edu.sg
Kovac
Branka
B
Klasinc
Leo
L
Ostrovskii
Vladimir A
VA
D002627:Chemistry, Physical / Q000379:methods; D003514:Cyclohexylamines / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009287:Naphthyridines / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010433:Pentylenetetrazole / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D013053:Spectrophotometry / Q000379:methods*; D014466:Ultraviolet Rays
D003514:Cyclohexylamines; D009287:Naphthyridines; D010720:Phosphines; C030435:1,2-cyclohexanediamine; D009584:Nitrogen; D010433:Pentylenetetrazole