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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 21, Number 1
JKCSEZ 21(1)
February 20, 1977 

MO Studies of Configuration and Conformation (Ⅲ). Conformations of Some 2-Substituted Furan, Thiophene and Pyrrole Carbonyl Compounds

배치와 형태에 관한 분자궤도함수론적 연구 (제3보). Furan, Thiophene 및 Pyrrole 카르보닐 화합물의 2-치환체의 형태
Ikchoon Lee, Shi Choon Kim

이익춘, 김시준
EHT 분자궤도함수법 계산으로 9가지 furan, thiophene 및 pyrrole의 2-치환체의 우세한 형태를 구명하였다. 계산 결과는 furan 유도체의 우세한 형태는 trans형인데 이것은 주로 정전기적 상호작용에 의하여 안정화되어 있으며 thiophene에서는 hetero 고리의 S원자와 카르보닐 산소와의 전자적 콘쥬게이션이, 그리고 pyrrole에서는 정전기적 및 콘쥬게이션 효과가 안정한 형태를 결정하는데 작용하고 있다. EHT계산 결과는 실험결과와도 잘 일치된다.

Conformations of nine 2-substituted furan, thiophene and pyrrole compounds have been studied by EHT methods. The preferred conformations of furan derivatives were trans form, which were mainly stabilized by electrostatic interactions. For thiophenes, electronic conjugation between the ring S and carbonyl oxygen was dominant, while for pyrroles both the electrostatic and conjugation effects were operative in determining the preferred conformations. Results of EHT calculation agreed well with experimentally determined preferences.

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