分子模擬作為化學教學的有效工作：有機酸中酸性氫的電荷大小與酸相對強度的相關性研究為例

Molecular Modeling as a Useful Tool in Teaching：Computational Study of The Correlation Between Electric Charge on Acidic Hydrogens and Acid Strength

10.6202/THJ-2015-11-07

蔡明松(Ming-Sung Tsai)

分子模擬 ； 密度泛函理論 ； 酸性氫 ； molecular modeling ； DFT (density functional theory) ； acidic hydrogen

慈惠學報

11期（2015 / 12 / 01）

73 - 83

繁體中文

由於電腦科技發達，使得量子化學計算逐漸廣泛用化學研究及化學教學上。特別是近代的分子模擬軟體結合使用者方便的圖形技術使得量子化學計算結果作為化學教學更具有實用性。本篇是利用密度泛函理論(density functional theory；DFT)方法研究有機酸中酸性氫的正電荷密度大小與酸的強度之間關係來解釋取代基效應對酸強度的影響。計算結果顯示有機酸的酸性氫的正電荷大小與酸的強度有正的關連。從這例子的理論計算結果更容易令學生想像取代基及分子結構對酸強的影響。

Quantum chemical calculation can play an ever increasing role in chemical research and teaching. Recently, molecular modeling software tightly connected via a graphical user interface offers the utility of molecular models in chemistry education. Therefore, in the present study, we will use DFT (density functional theory ) calculations to explore what extent the electronic charge of acidic hydrogen on neutral acids to reflect acid strengths. Results of calculation showing the correlation between electronic charge on the acidic hydrogen and acid strength is positive correlation. According to the results of calculation showing that the electronic charge of acidic hydrogen to predict acid strength is reasonable.

1. Foresman, J.B.,Frisch, Æ.(1996).Exploring chemistry with electronic structure methods.Pittsburgh, PA:Gaussian Inc.
2. Foster, J.P.,Weinhold, F.(1980).Natural bond orbital methods.Encyclopedia of Computational Chemistry,Chichester, UK:
3. Geib, R.I.,Schwartz, L.M.(1976).Aqueous dissociation of dihydroxycyclopropenone (deltic acid).J. Chem. Soc., Perkin Trans.,8,930.
4. Hehre, W.J.(2003).A quide to molecular mechanics and quantum chemical calculations.Irne, CA:Wavefunction, Inc.
5. Hehre, W.J.(2010).Spartan version 10.Irvin, CA:Wavefunction Inc.
6. Koch, W.,Holthausen, M.C.(2001).A chemist′s guide to density functional theory.Weinheim:Wiley-VCH.
7. Lee, C.,Yang, W.,Parr, R.G.(1988).Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.Phys. Rev. B,37,785.
8. Miehlich, B.,Savin, A.,Stoll, H.,Preuss, H..Results obtained with the correlation energy density functionals of becke and Lee Yang and Parr.Chem. Phys. Lett.,157,200.
9. Morrison, R.T.,Boyd, R.N.(1992).Organic Chemistry.India:Prentice Hall.
10. Tro, N.J.(2006).Introductory chemistry.Prentice Hall:Pearson education, Inc..
11. Wavefunction, Inc(2006).Spartan 06 for window: Tutorial and user′s guide.Irvin, CA:Wavefunction Inc.
12. Wikipedia, the free encyclopedia (2009) Squaric acid 取自https://en.wikipedia.org/wiki/Squaric_acid。(2009)
13. Zumdahl, S.S.,DeCoste, D.J.(2008).Introductory chemistry: A foundation.Boston:Houghton Mifflin Company.

1. 蔡明松(2017)。理論探討酚與過渡金屬形成錯合物對酚的酸性的影響。慈惠學報，13，114-124。