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Rotational Isomers of N-Alkyl-N-(o-acylphenyl)acetamides
Yeong-Joon Kim,Younbong Park,Kwanghee Koh Park 충남대학교 소재화학연구소 2007 소재화학연구소 논문집 Vol.- No.2
We have studied molecular structure of N-alkyl-N-(o-acylphenyl)acetamides 1?3 by <SUP>1</SUP>H NMR spectroscopy. The <SUP>1</SUP>H NMR spectra clearly displayed that two rotational isomers are present in solution and two geminal N?CH₂ protons are magnetically nonequivalent. This was explained by restricted rotations about both the amide N?CO bond and the aryl-nitrogen bond. The ratios of exo (benzene ring trans to carbonyl) and endo rotamers were estimated to be 6?8:1 from the <SUP>1</SUP>H NMR spectra. The X-ray analysis of N-ethyl-N-(o-benzoylphenyl) acetamide 1 showed that the crystal has exo-form. The rotations about both the amide N?CO bond and the aryl-nitrogen bond were slower on the NMR time scale.