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KMID : 1059519890330050538
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Journal of the Korean Chemical Society
1989 Volume.33 No. 5 p.538 ~ p.544
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Solvent Dependence and Component of Linear Free Energy Relationship on the Chemical Shift of Methylene Proton in 1-(phenoxymethlyl)benzotriazole Derivatives
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Sung Nack-Do
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Abstract
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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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KEYWORD
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