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系統識別號 U0002-2007201115151900
中文論文名稱 Trihydroxyazepanes的結構與13C化學 位移之理論計算研究
英文論文名稱 Theoretical Studies of Structures and 13C NMR Chemical Shifts for Trihydroxyazepanes
校院名稱 淡江大學
系所名稱(中) 化學學系博士班
系所名稱(英) Department of Chemistry
學年度 99
學期 2
出版年 100
研究生中文姓名 葉寶玲
研究生英文姓名 Pao-Ling Yeh
學號 893170018
學位類別 博士
語文別 中文
口試日期 2011-06-28
論文頁數 195頁
口試委員 指導教授-王伯昌
委員-陳正隆
委員-江志強
委員-高惠春
委員-施增廉
委員-鄧金培
中文關鍵字 七圓環醣水解酵素抑制劑  幾何結構最佳化  化學位移  平均絕對誤差 
英文關鍵字 conformational analysis  NMR calculation  trihydroxyazepane 
學科別分類
中文摘要 本論文係研究三種trihydroxyazepanes異構物之穩定構形,由於七圓環醣水解酵素抑制劑結構的易變性,所以可以藉由理論計算去預測可能的結構。幾何結構最佳化是使用Gaussian 03軟體中的DFT/B3LYP/6-311++G(d,p),得到每種異構物各有28個構形,其中能量較低為相對穩定的構形,再以Gibbs自由能算出28個構形之Boltzmann分佈。接著針對三種異構物相對穩定的構形,進行13C NMR化學位移計算,並與已報導之數值做比對。我們採用GIAO/HF、GIAO/DFT/OPBE及GIAO/DFT/B3LYP搭配四種不同的基底函數,包括6-311++G(d,p)、6-311+G(2d,p)、cc-pVDZ及cc-pVTZ做單點計算。相對穩定的構形,其13C NMR化學位移之平均絕對誤差(Mean Absolute Error,MAE)也相對較小。因為實驗的化學位移是許多構形的平均貢獻,我們考慮Boltzmann分佈將數個構形混合去進行13C NMR化學位移計算,構形混合的MAE比單一構形的MAE小,而且實驗的化學位移和理論計算的化學位移趨勢符合。其中使用HF(Hartree-Fock,HF)方法搭配cc-pVTZ基底函數,使用OPBE方法搭配6-311+G(2d,p)基底函數及使用B3LYP方法搭配cc-pVDZ基底函數,計算所得之化學位移最接近實驗值。針對其他相關結構易變的七圓環醣水解酵素抑制劑,此結果可以作為參考的依據。
英文摘要 Owing to the conformational flexibility for trihydroxyazepanes, the theoretical prediction should be helpful for generating appropriate conformations. DFT/B3LYP/6-311++G(d,p) calculations of three isomers for trihydroxyazepanes are presented to obtain 28 conformations for each isomer. The Boltzmann distribution was considered to calculate the population of each conformation. The GIAO/DFT/OPBE, GIAO/DFT/B3LYP and GIAO/HF single point calculations with four different basis sets, including 6-311++G(d,p), 6-311+G(2d,p), cc-pVDZ and cc-pVTZ of the relative stable conformations of trihydroxyazepanes were conducted to generate their 13C NMR chemical shifts. The calculated chemical shifts are compared with the experimental ones. The MAEs (Mean Absolute Error, MAE) of the 13C NMR chemical shifts for the relative stable conformations are smaller. Moreover, the experimental 13C NMR chemical shifts gave only the average contribution of all conformations. The observed average chemical shifts displays improvement over that of each individual conformation. Good choices to evaluate the theoretical chemical shifts for these conformations are HF/cc-pVTZ, OPBE/6-311+G(2d,p) and B3LYP/cc-pVDZ. The calculated 13C NMR chemical shifts are in good agreement with the experimental NMR data of trihydroxyazepanes.
論文目次 中文摘要 I
英文摘要 II
目錄 III
表目錄 VI
圖目錄 X
第一章 緒論 1
1-1 前言 1
1-2 醣水解酵素 5
1-3 醣水解酵素抑制劑 6
1-3-1可逆性抑制劑 6
1-3-2不可逆性抑制劑 7
1-4醣水解酵素抑制劑的結構 9
1-5核磁共振 12
1-6研究概況 14
1-7 研究動機 23

第二章 量子化學計算理論與方法 25
2-1 前言 25
2-2 量子力學 28
2-2-1 薛丁格方程式(Schrödinger Equation) 29
2-2-2 原子單位(Atomic Units) 32
2-2-3 波恩-歐本海莫(Born-Oppenheimer)近似法 33
2-2-4 分子軌域理論 35
2-3量子化學計算近似法 37
2-3-1 Hartree — Fock量子化學計算近似法 37
2-3-2密度泛函數理論 42
2-4基底函數組(Basis Set) 49
2-4-1最小基底函數STO-3G 52
2-4-2分離價層的基底函數(Split-Valence Basis Sets) 54
2-4-3極化函數(Polarization Function) 55
2-4-4擴散函數(Diffuse Function) 57
2-4-5考慮相干的基底函數(Correlation Consistent basis set) 58
2-5分子性質(Molecular Properties) 59
2-5-1外加磁場的微擾處理( Molecular Field Perturbation ) 60
2-5-2分子磁性的原點關連性( Gauge Dependence ) 62
2-6 13C化學位移 64

第三章 研究設備 65
3-1 硬體設備 65
3-2 軟體設備 65

第四章 Trihydroxyazepanes的結構與化學位移 69
4-1 簡介 69
4-2 研究方法 70
4-3結果與討論 72
4-3-1 (3R,4R,5R)-trihydroxyazepanes 72
4-3-1-1分子幾何結構 72
4-3-1-2 13C NMR化學位移 90
4-3-2 (3R,4R,6S)-trihydroxyazepanes 106
4-3-2-1分子幾何結構 106
4-3-2-2 13C NMR化學位移 118
4-3-3 (3S,4R,6S)-trihydroxyazepanes 137
4-3-3-1分子幾何結構 137
4-3-3-2 13C NMR化學位移 149

第五章 結論 185
A.參考文獻 187
B.相關著作 195
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DFT and TD-DFT Investigations of Metal-Free Dye Sensitizers for Solar
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J. Mol. Struct. 2011 (revision)
Conformational analysis of a seven-membered ring azasugar, (3R,4R,6S)-trihydroxyazepane: comparison of GIAO calculation and experimental NMR spectra on 13C chemical shifts

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