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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 25, Number 6
JKCSEZ 25(6)
December 20, 1981 

 
Title
Determination of Reactivity by MO Theory (ⅩⅩⅠ). MO Theoretical Studies on Urethane Formation

분자궤도론에 의한 반응성의 결정 (제21보). 우레탄 형성에 관한 MO 론적 연구
Author
Ikchoon Lee, Nag Young Jung, Shi Choon Kim

이익춘, 정낙영, 김시준
Keywords
Abstract
이소시안산 에스테르와 알코올이 반응하는 우레탄 형성반응에서 알코올분자가 이소시안산 에스테르에 접근하는 배향성을 MO론적으로 고찰하였다. EHT 및 CNDO/2 계산결과에 의하면 알코올이 이소시안 산에스테르 평면과 동일한 평면으로 접근하는 4-중심 메카니즘으로 진행되는 것이 유리함을 알 수 있었다. 또한 알코올의 O-H기에 있는 산소가 수소보다 먼저 이소시안산 에스테르의 탄소에 접근함을 알 수 있었고 이 반응은 전하조절반응임을 밝혔다.

For the urethane formation reaction of isocyanate with alcohol, orientation of approach of alcohol toward isocyanate was investigated theoretically by means of MO method. As a result of EHT and CNDO/2 calculations, it was found that the reaction proceeding via 4-centered mechanism, in which ROH is coplanar with isocyanate plane was energetically favored. It was also shown that the oxygen of ROH attacks the isocyanate carbon prior to the formation of 4-center complex. The reaction was found to be a charge controlled one.

Page
361 - 366
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