本篇論文主要是以天然鍵性軌域理論（NBO）的『donor-acceptor interaction』概念為基礎，探討有機酸衍生物的水解反應。首先我們討論無攻擊劑狀態時，有機酸衍生物分子內的電荷轉移情形，再衍生到這些分子發生水解反應時，分子內及分子間的電荷移轉。

計算有機酸衍生物，我們發現碳醯基氧上孤對電子對具有削弱鄰近σC-X*鍵的能力，且愈易離去的離去基，其『lpC=O→σC-X*』能量越大。主要是因為愈易離去的離去基，本身分子中的σC-X* 軌域能量較穩定，所以『lpC=O→σC-X*』能量較大。

在模擬水解反應部分，我們分成有機酸衍生物（CH3COX，X＝F、Cl、Br、OCH3）的中性水解反應及乙酸甲酯（CH3COOCH3）的鹼性水解反應。我們得到無論中性與鹼性的狀況，攻擊劑上的孤電子對主要都是扮演削弱πC=O的角色，且削弱πC=O之後，間接提升碳醯基氧上孤電子對的軌域能量，縮短孤電子對與σC-X*的能差。攻擊劑以這樣的方式幫助反應進行，但是最後離去基的離去仍取決於σC-X*本身的軌域能階高低。模擬乙醯氟與乙酸甲酯的中性水解及乙酸甲酯的鹼性水解，我們發現它們本身σC-X*軌域能量較乙醯溴及乙醯氯來的高，因此就算攻擊劑有幫助反應進行，最後離去基仍未離去。

Donor-acceptor interaction concept of the natural bond orbital theory was applied to evaluate charge transfer in carboxylic acid derivatives and in hydrolysis of carboxylic acid derivatives in our study respectively.

In our calculations of carboxylic acid derivatives, lone pair on the oxygen atom of carbonyl group was observed to donate to neighbor σC-X* orbital. And the better leaving group has more 『lpC=O→σC-X*』interaction energies by it’s lowerσC-X* orbital energy.

For hydrolysis of carboxylic acid derivatives, we calculate CH3COX（X= F、Cl、Br、OCH3）in water and CH3COX（X= OCH3）in base-catalyzed surroundings respectively. The results are similar in different cases, that lone pair on nucleophilic reagent mainly donates to πC=O* orbital, result in energy increasing of lone pair on the oxygen atom of carbonyl group. Furthermore, the energy gap between the lone pair on the oxygen atom of carbonyl group and σC-X* orbital will get smaller. The nucleophilic reagent helps hydrolysis reaction processing with this way. However the leaving group leaves or not depending on σC-X* orbital energy. To simulating hydrolysis of acetyl fluoride and methyl acetate in water and hydrolysis of methyl acetate in base-catalyzed surroundings, we found that their σC-X* orbital energy is higher than acetyl chloride and acetyl bromide. Although the nucleophile reagent helps reaction processing, the leaving group still did not leave.

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