研究生: |
馮立婷 Li-Ting Fong |
---|---|
論文名稱: |
研究亞硝基及一氧化氮在雙亞硝基鐵及碳氫異位紫質鐵錯合物間轉換機制及水溶性碳氫異位紫質鐵錯合物之亞硝酸鹽還原反應 Study on Nitrite Reduction and NO Transformation between DNIC and Iron N-confused Porphyrin Complexes and Nitrite Reduction Using Water-soluble Iron N-confused Porphyrin Complexes |
指導教授: |
林昇佃
Shawn D. Lin 洪政雄 Chen-Hsiung Hung |
口試委員: |
廖文
Wen-Feng. Liaw 王雲銘 Yun-Ming Wang 江明錫 Ming-Hsi Chiang |
學位類別: |
博士 Doctor |
系所名稱: |
應用科技學院 - 應用科技研究所 Graduate Institute of Applied Science and Technology |
論文出版年: | 2015 |
畢業學年度: | 104 |
語文別: | 英文 |
論文頁數: | 161 |
中文關鍵詞: | 硝基及一氧化氮在雙亞硝基鐵 、碳氫異位紫質鐵錯合物 、水溶性碳氫異位紫質鐵錯合物 、亞硝酸鹽還原反應 |
外文關鍵詞: | NO Transformation, DNIC, Iron N-confused Porphyrin Complexes, Nitrite Reduction, Water-soluble Iron N-confused Porphyrin Complexe |
相關次數: | 點閱:287 下載:7 |
分享至: |
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本文第一個部分是研究碳氫異位紫質鐵錯合物與具有硝基及一氧化氮的DNICs之間的反應。我們以碳氫異位紫質鐵錯合物中心去了解一氧化氮由[PPh3][Fe(NO)2(ONO)2]轉移至紫質中心的反應過程。研究結果顯示 [FeII(HCTPPH)Br]與[FeIII(HCTPP)Br]具有還原亞硝基鹽的能力。其中由[Fe(HCTPPH)Br]與[PPh3][Fe(NO)2(ONO)2]在2:1當量反應中,使用同位素[PPh3] [Fe(NO)2(O15NO)2]當起始物,我們得到1:1的[Fe(CTPP)(14NO)] 與 [Fe(CTPP)(15NO)]的混合產物。[PPN][Fe(NO)2(ONO)2]則轉換成[PPh3][Fe(14NO)(15NO2)Br2]。結果顯示一當量的一氧化氮由DNIC的亞硝酸還原而來,而另一當量由DNIC上的一氧化氮直接轉移。我們以實驗確認,一氧化氮轉移至碳氫異位紫質鐵錯合物的同時釋放出羥基自由基。在1:4 [PPN][Fe(NO)2(ONO)2]與[FeII(HCTPPH)Br] 當量比下的反應結果顯示[PPh3][Fe(NO)2(ONO)2] 能夠提供4當量的一氧化氮。
第二部分是研究具有水溶性的碳氫異位紫質鐵錯合物模擬亞硝酸鹽還原反應。首先利用磺酸化將碳氫異位紫質錯合物化合成NCPS再金屬化合成具有高水溶性的[FeII(HNCPSH)Br]。其中由[FeII(HNCPSH)Br] 與NaNO2在1:1當量反應中,顯示[FeII(HNCPSH)Br]可進行亞硝酸還原反應並獲得產物{Fe(NO)}7 [Fe(HNCPS)(NO)] ,再被反應中產生的氫氧自由基氧化形成{Fe(NO)}6 [Fe(NCPS)(MeOH)(NO)]。當系統中有過多的亞硝酸鹽,[Fe(HNCPS)(NO)]與 [Fe(NCPS)(MeOH)(NO)]皆會直接轉變成{Fe(NO)}6 [Fe(NCPSO)(NO)]。在[FeIII(HNCPS)Br]為反應物的狀況下,也能夠會進行亞硝酸還原反應並直接獲得產物[Fe(NCPS)(MeOH)(NO)]與[Fe(NCPSO)(NO)]無須經過{Fe(NO)}7 [Fe(HNCPS)(NO)],其中[Fe(NCPS)(MeOH)(NO)] 再被反應中產生的氫氧自由基氧化形成{Fe(NO)}6 [Fe(NCPSO)(NO)]。最後,我們也證實亞硝酸還原反應可以在水相中得到與與甲醇中相同結果產物。
We studied the nitrite reduction and NO transfer between O-bound nitrito coordinated [PPN][Fe(NO)2(ONO)2] and iron N-confused porphyrin center. The nitrite reduction reaction activities converts iron(II) and iron(III) N-confused porphyrin complexes to [Fe(HCTPP)(NO)], [Fe(CTPP)(NO)], or [Fe(CTPPO)(NO)]. Under a 2:1 iron porphyrin/DNIC mole ratio, using 15N isotope labelled [PPh3] [Fe(NO)2(O15NO)2] as the starting DNIC, a 1:1 mixture of [Fe(CTPP)(14NO)] and [Fe(CTPP)(15NO)] are obtained while the DNIC transformed into [PPh3][Fe(14NO)(15NO2)Br2], suggesting that one equivalent of nitrite reduction and one equivalent of direct NO transformation have occurred. NO has found to transfer and coordinate to the axial position of iron(II) N-confused porphyrin center with the release of a hydroxyl radical while the second coordinated nitrite (NO2) is reduced to NO on DNIC coordination sphere to complete the conversion of [PPh3] [Fe(NO)2(ONO)2] into [PPh3][Fe(NO)2Br2]. Under a 4:1 iron porphyrin/DNIC mole ratio, our results demonstrate that [PPN][Fe(NO)2(ONO)2] can serve as a four equivalent nitric oxide donating molecule.
To explore the tendency of nitrite reduction in aqueous phase, we have synthesized water-soluble N-confused porphyrin iron(II) complexes. Tetraphenyl N-confused porphyrin (NCTPP), bearing four 4-sulfonatophenyl groups at the meso positions, and its iron(II) complex, [FeII(HNCPSH)Br], were synthesized. The solution IR studies showed the formation of {Fe(NO)}7 [Fe(HNCPS)NO] as the final product when 0.5 equiv of sodium nitrite was reacted with one equiv of starting [FeII(HNCPSH)Br] in MeOH. We have also confirmed that NaNO2 can directly react with {Fe(NO)}7 and {Fe(NO)}6 iron nitrosyl complexes to result O-atom insertion between Fe-C bond and obtained {Fe(NO)}6 [Fe(CTPPO)NO]. The nitrite reduction reaction in aqueous solution observed the formation of iron nitrosyl complex as in MeOH
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