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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 33, Number 5
JKCSEZ 33(5)
October 20, 1989 

Solvent Dependence and Component of Linear Free Energy Relationship on the Chemical Shift of Methylene proton in 1-(phenoxymehtyl) benzotriazole Derivatives.

1-(phenoxymethyl)benzotriazole 유도체 중 methylene 양성자의 chemical shift 에 관한 자유에너지 관계의 조성과 용매 의존성
Nack-Do Sung

1-(phenoxymethyl)benzotriazole(1)과 1-(thiophenoxymethyl)benzotriazole(2) 유도체중의 X 치환기가 전자를 끄는 세기(ρ<0)와 methylene group의 인접 Y원자에 의한 local diamagnetic effect(Y=O(1)>S(2)), 그리고 용매의 극성파라미터(Er=Kcal/mol:acetone;42.2>chloroform;39.0)가 클수록 methylene group의 수소원자(Hm)와 용매사이에 B-형의 수소결합성이 증가되었으며 (1)의 methylene group 에 대한 substituent chemical shift(CH2-SCS)에 미치는 자유 에너지 직선관계(LFER)의 조성은 아세톤 용액 중에서 장(F)(또는 유발(I))-효과 보다 공명(R)-효과가 더 크게 나타나는 용매 의존적인 경향이었다.

The increase of B-type hydrogen bonding character between the hydrogen atom(Hγ) of methylene group in 1-(phenoxymethyl)benzotriazole (1) and 1-(thiophenoxymetyl)benzotriazole (2) derivatives, and solvents was caused by some factors such as;electron withdrawing strength (ρ > 0) of X-substituent; local diamagnetic effect by Y atom (Y = O(1) > S(2)) with adjacent methylene group; and solvent polarity parameter (ET = Kcal/mol; acetone; 42.2 > chloroform; 39.0). From the basis on the findings, linear free energy relationship (LFER) components on the substituent chemical shift of methylene group (CH2-SCS) in (1) exhibited a tendency that resonance(R)-effect was much larger than field(F) (or inductive(I))-effect in acetone and that the electrical effects were depend upon the solvent.

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