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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 34, Number 3
JKCSEZ 34(3)
June 20, 1990

Title	Theoretical Studies on Electrophilic Substitution of Five-membered Heteroaromatic Compounds with Isopropyl Cation 5각-이종원자 방향족 고리화합물과 이소프로필 양이온간의 친전자 치환반응에 관한 이론적 연구 (1)
Author	Ikchoon Lee, Chang Kon Kim, Bon-Su Lee 이익춘, 김창곤, 이본수
Keywords
Abstract	Theoretical studies on the electrophilic substitution reactions of five-membered heteroaromatic compounds, furan, pyrrole and thiophene, with isopropyl cation were carried out using the MNDO method. The results indicated that site selectivities of α,β and hetero-atoms are not controlled by electrostatic interactions but are determined mainly by charge trasfer stabilization between the HOMO of heteroaromatics and the LUMO of the electrophile. The reactivity order for αandβ positions was pyrrole > furan > thiophene, in agreement with the solution-phase as well as the gas-phase experimental results.
Page	248 - 254
Full Text	PDF

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