13C-NMR and Molecular Orbital Studies of Protonation to Formanilides
作者:
Chikakiyo Nagata,
Eiichi Miyata,
Tsutomu Horikiri,
Shigeyuki Tanaka,
期刊:
Spectroscopy Letters
(Taylor Available online 1979)
卷期:
Volume 12,
issue 4
页码: 287-295
ISSN:0038-7010
年代: 1979
DOI:10.1080/00387017908069155
出版商: Taylor & Francis Group
关键词: 13C-NMR;Molecular Orbital;Protonation;Formanilides
数据来源: Taylor
摘要:
The effect of protonation to formanilides was studied by measurements of13C-NMR chemical shifts in CDCl3and methanesulfonic acid. It was found that the13C shift of the ring carbon, to which the amide group is attached, exhibits an upfield shift by the protonation, whereas the peaks of the rest of ring carbons and carbonyl carbon shift downfield. The protonation-induced shifts of the ring carbons were found to be roughly correlated with the differences of the total electron densities between formanilides and their monocations. From the comparison between the protonation-induced shifts and the differences of the total electron densities at the carbons, especially at the carbonyl carbon, it is suggested that N-protonation is partly involved, although O-protonation seems to be dominant.
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