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KMID : 1059519920360030366
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Journal of the Korean Chemical Society
1992 Volume.36 No. 3 p.366 ~ p.375
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Determination of Reactivity by MO Theory. Part 79. MO Theoretical Studies on Aminolysis of Carbamates
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Park Byung-Seo
Lee Ik-Choon
Cho Jeoung-Ki
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Abstract
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The aminolysis of carbamates are studied MO theoretically using AM1 method. The results indicated that the reactivity is determined by bond-making and-breaking and steric effects; as a result the BAC2 mechanism is favored due to favorable contribution of bond formation in agreement with experimental results. We found that although thermal 2＋2 reaction is forbidden, it becomes allowed when the total electrons involved are six in a four-center reaction and proceeds by a consecutive onestep mechanism. Comparison of activation barriers show that greater energy is required in breaking a sigma bond compared with the energy required for breaking a π bond, by 17 kcal/mol and the six membered ring structure is favored about 5 kcal/mol sterically.
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