N-(2-Nitrophenyl)proline: an intramolecular hydrogen bond forming reagent for the determination of the absolute configuration of primary amines.
N-(2-Nitrophenyl)proline (2-NPP) amides of primary amines have a conformational preference for intramolecular hydrogen bonding. Because of the strong and selective anisotropic effects on the amine substituents, the absolute configuration of alpha-chiral primary amines can be assigned by comparing the 1H chemical shifts of diastereomeric 2-NPP amides.
Ahn
Hee Choon
HC
Department of Chemistry and Center for Electro- and Photo-Responsive Molecules, Korea University, Seoul 136-701, Republic of Korea.
Choi
Kihang
K
D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D009574:Nitro Compounds / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D000588:Amines; C523864:N-(2-Nitrophenyl)proline; D009574:Nitro Compounds; D011392:Proline