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KMID : 1059519970410070351
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Journal of the Korean Chemical Society
1997 Volume.41 No. 7 p.351 ~ p.356
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Kinetics and Mechanism of the Hydrolysis of 1-Halo-3-Phenyl-1,2-Propadienes
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Lee Kang-Ryul
Yoo Hil-Ra
Jung In-Chan
Heo Tae-Seong
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Abstract
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Extended Hijckel Molecular Orbital(EHMO) calculations of haloallene (1-halo-3-Pheny-1,2-propadiene) derivatives have been performed. From the MO calculation data and kinetic experimental results, the mechanism for the hydrolysis of haloallenes is proposed.; Below pH 8.0, the hydrolysis proceeds through a solvent assisted S,l mechanism involving the formation of carbonim ion II as intermediate. However above pH 9.5, the hydrolysis proceeds through an Sn2' mechanism via transition state III.
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KEYWORD
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