臺灣博碩士論文加值系統

藉由核磁共振光譜技術研究取代基對1-芳香基偶氮-2-萘酚系列化合物互變異構化時的影響。從13C化學位移的變動中發現，化合物C(2)位置受到苯環上取代基性質影響最為敏感，其化學位移變化值達24 ppm。因此，由C(2)化學位移的變動並從取代基化學位移值與自由能對Hammett常數(σ+)的線性關係來探討取代基效應。兩種方法中皆得到負斜率值，分別為ρ=-8.74與ρ=-1.38，顯示拉電子基團有利於腙形式異構物形成。藉由1-苯基偶氮-2-萘酚化合物在10種溶劑中C(2)位置的化學位移變化探討溶劑效應，而溶劑包含質子提供者、質子接受者與芳香烴類等。推電子特性的取代基對溶劑性質更為敏感，更利於偶氮形式異構物形成。而從動態核磁共振技術得到的自由能顯示，拉電子特性取代基利於腙形式異構物的形成。在弛豫實驗中，化合物上的碳原子受取代基影響不大。而黏度與弛豫時間則呈反比關係。
在質譜上，利用電子電離質譜研究系列化合物碎裂裂片來探討取代基效應。藉由分子離子與碎片離子間的離子強度比例[Imolecular ion/(I171amu+I143amu+I115amu)]與Hammett常數的線性關係來探討在碎裂時的取代基效應。而從此方法得到負斜率值為ρ=-0.778，顯示拉電子基團的分子離子不穩定。並在碎裂過程中發現一個長距離的氫轉移現象產生。

The substituent effect on azo-hydrazone tautomerization of 1-aryldiazo-2-naphthalenol is studied by means of NMR and MS analysis. Among the 13C chemical shifts, the C(2) of this series compound is the most sensitive to the variation in the nature of substituent on the phenyl ring. Therefore, the variation in the chemical shifts of C(2) is used to probe the substituent effect by using the substituent chemical shifts and free energy vs. Hammett’s constant (σ+). Both methods give a negative correlation slope, which are ρ=-8.74 and ρ=-1.38 , indicating the electron-withdrawing groups favor the hydrazone tautomer form. The effect on the chemical shifts of C(2) of 1-phenyldiazo-2-naphthalenol in ten solvents can be classified as the solvent with a proton-donor, proton-acceptor and arenes system. The substituent with electron-donating character is more sensitive to the nature of solvent and it favors the azo form. Free energy obtained from the dynamic NMR technique indicates the tautomerization favors the hydrazone-form for the substituent with electron-withdrawing character. The relaxation time of carbon are slight affected by the size of substituents. In the viscosity study, an inverse-law relationship between relaxation times and viscosity was observed.
An electron-ionization (EI) mass spectra of a series of 1-aryldiazo-2-naphthalenol was obtained for studying the substituent effect on the fragmentation. The correlation between the ratio, molecular ion and fragment ion, and Hammett’s constants is applied to examine the effect of the substituent on the fragmentation. The negative correction between the ratio, Imolecular ion/(I171amu + I143amu + I115amu), and Hammett’s constants, which is ρ=-0.778, indicates an electron-withdrawing group destabilized the molecular ion. An unusual long-range hydrogen transfer demonstrates an important role in the fragmentation process.

圖目錄 Ⅳ
表目錄 Ⅵ
附圖目錄 Ⅷ
中文摘要 XIV
Abstract XVI
第一章、緒論 1
第一節、前言 1
第二節、酮-烯醇互變異構 (Keto-Enol Tautomerism) 6
第三節、Hammett方程式 11
第四節、核磁共振弛豫理論 14
一、自旋-晶格弛豫 (Spin-Lattice Relaxation) 16
二、自旋-自旋弛豫 (Spin-Spin Relaxation) 17
三、T1的測量方法 18
四、T2的測量方法 20
第五節、質譜術的簡介 22
一、質譜儀的歷史 22
二、質譜儀的簡介 22
第六節、研究動機 28
第二章、實驗部分 30
一、[NMP]+[CH3SO3]- ，離子液體的製備 30
二、1-(4′-甲基苯偶氮)-2-萘酚化合物(7)製備 31
三、1-(4′-氨基苯偶氮)-2-萘酚化合物(4)製備 36
四、1-(2′-甲氧羰基苯偶氮)-2-萘酚化合物(15)製備 38
五、1-(4′-乙醯胺基苯偶氮)-2-萘酚化合物(16)製備 39
第三章、結果與討論 41
第一節、核磁共振光譜部分 41
一、取代基效應對13C化學位移的影響 41
二、溶劑效應對13C化學位移的影響 48
三、互變異構的定量分析 52
四、熱力學分析 57
五、取代基效應對弛豫時間(T1)的影響 63
六、溶劑效應對弛豫時間(T1)的影響 65
七、分子的轉動 67
八、溶氧效應對弛豫時間的影響 70
第二節、質譜部分 72
一、一般裂解過程 72
二、取代基效應影響 78
三、鄰位效應(Ortho effect) 82
第四章、結論 84
第五章、儀器與藥品 86
一、儀器 86
二、藥品 86
第六章、參考文獻 89
第七章、附圖 102

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