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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 17, Number 3
JKCSEZ 17(3)
June 20, 1973 

On the Correlation of the Carbonyl Stretching Frequency with Substituents in Benzanilides

벤즈아닐리드에 있어서 치환기가 카르보닐 신축진동에 미치는 영향
Soon-Yung Hong, Yong-Tae Park, Won-Hyung Choi

홍순영, 박용태, 최원형
Hammett형의 식(ν=ν0 + ρσ)을 적용하여 벤즈아닐리드에 있어서의 카르보닐 신축진동과 치환기의 상관관계를 조사하였다. 치환기가 C-페닐기에 있을때는 σ보다 σ+ 와 더 좋은 상관관계를 나타내었고 한편 치환기가 N-페닐기에 있을때는 σ와 더 좋은 상관관계를 나타내었다. 치환기가 C- 및 N- 양페닐기에 동시에 있을때는 이들 치환기는 카르보닐 신축진동에 서로 독립적으로 적용하였다. 이와같은 결과를 벤즈아닐리드의 구조를 이용하여 고찰하였다.

The correlation of the infrared carbonyl stretching frequency with substituents in benzanilides has been studied. The Hammett-type equation(1) was adopted for this correlation. Substituents in a C-phenyl-ring gave a better correlation with σ+ rather than σ, meanwhile, substituents in a N-phenyl-ring gave a better correlation with σ. When substituents are placed on both C-phenyl and N-phenyl ring, they influenced the carbonyl stretching frequency reasonably independently of each other. A conformation of benzanilide which accounts for the above observation has also been discussed.

193 - 197
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