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| Type |
Poster Presentation |
| Area |
Physical Chemistry |
| Room No. |
Event Hall |
| Time |
4월 20일 (금요일) 11:00~12:30 |
| Code |
PHYS.P-215 |
| Subject |
Substituent Effect of Chloromethyl along the Positions on Benzoyl Chloride System in Solvolys |
| Authors |
Kyoung-Ho Park
Department of Applied Chemistry, Hanyang University, Korea |
| Abstract |
The oomaprison of three derivatives that the benzoyl chloride system contining a single chloromethyl substituent was performed by the Grunwald-Winstein equations, the solvent isotope effect and activation parameters. The chloromethyl substituent has chlorine atom on mehtyl group, so it does not have a resonance effect toward benzoyl chloride system. It has only the steric hindrance and the inductive effect due to the competition of a electron donating methyl and a strong electonegative chlorine atom. In conclusion, the solvolysis mechanism of chloromethylbenzoyl chloride was increased the ionization character by moving the substituent from meta to para-postion. This aspect is interpreted that the meta-postion is not active site for the inductive effect of chloromethyl substituent on benzoyl chloride system, but para-chloromethylbenzoyl chloride does well. So the meta-substituted compound has the addition-elimination mechanism in nucleophilic solvents, while the para-substituted compound has the associative SN2 mechanism in same condition. Specially, ortho-compound has the dissociative SN2 mechanism in all solvents, because of the steric hindrance. |
| E-mail |
piroho@hanyang.ac.kr |
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121st General Meeting of the KCS