研究生: |
那加 Harisomayajula, Naga Venkata Satyachand |
---|---|
論文名稱: |
第六族過渡金屬五重鍵錯合物與多銅金屬鏈的製備與化性分析 Preparation and Reactivity Studies of Quintuply Bonded Group VI Metal Complexes and Extended Copper(I) Atom Chains |
指導教授: |
蔡易州
Tsai, Yi-Chou |
口試委員: |
劉瑞雄
Liu, Rai-Shung 鄭建鴻 Cheng, Chien-Hong 許智能 Hsu, C N 劉學儒 Liu, Hsueh-Ju |
學位類別: |
博士 Doctor |
系所名稱: |
理學院 - 化學系 Department of Chemistry |
論文出版年: | 2018 |
畢業學年度: | 106 |
語文別: | 英文 |
論文頁數: | 269 |
中文關鍵詞: | 第六族金屬 、五鍵 、鹵醯化 、延長金屬鏈 、DFT-理論計算 |
外文關鍵詞: | Group VI metals, Quintuple bond, Haloacylation, Extended Metal Atom Chains, DFT-Calculations |
相關次數: | 點閱:2 下載:0 |
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此論文描述具金屬-金屬五重鍵之第六族雙金屬錯合物其合成與反應性探討;並藉由設計具有數個氮原子的有機配基,所建構而成的多銅金屬鏈(EMACs),經過實驗證實雙銅之間所具有的金屬-金屬之間的吸引力(Cuprophilicity)。
第一個章節論述以雙鉬五重鍵金屬錯合物[Mo2(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (1)進行簡單的鹵醯化反應。以化合物1與不同的鹵醯反應可得到具β-halo-α,β-quadruply-bonded dimolybdenum acyl complexes anti-Mo2(X)(μ-κ2-OCR)[μ-κ2-HC(N-2,6-iPr2C6H3)2]2 (R = Me, X= Cl (3); R = C6H5, X = Cl (4), Br (5); R= 4-FC6H4, X= Cl (6); R = 2-MeC6H4, X = Cl (7)). 而透過密度泛函理論計算Mo2(Cl)(μ-κ2-OCMe)[μ-κ2-HC(N-2,6-iPr2C6H3)2]2,可以假設其會與oxo-alkylidyne Mo2(O)(μ-Cl)(μ-CMe)[μ-κ2-HC(N-2,6-iPr2C6H3)2]2 以大約100:1的比例達成平衡。在此具有親和性的Mo=O的官能團被證明與多種親電試劑具有反應性,化合物3-7有嘗試與不同當量數的鹵醯進行鹵醯化反應而得到次烷基以架橋形式鍵結在金屬中心的雙鉬金屬錯合物[Mo2(X)(µ-X)(µ-CR)(κ2-O2CR)(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (R = Me, X = Cl (10); R = C6H5, X = Cl (11), Br (12); R = 4-FC6H4, X = Cl (13); R = 2-MeC6H4, X = Cl (14)).為了瞭解氧代次烷基的產生與其功用,將化合物4與N-methylbenzimidoyl chloride和二苯基次膦酰氯反應得到兩個具苯次甲基的產物,分別是Mo2(Cl)(µ-Cl)(µ-CC6H5)(κ2-ONCH3C6H5)(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (17)和[Mo2(Cl)(µ-Cl)(µ-CC6H5)(κ2-O2PPh2)(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (18)。這些結果清楚的表示出卡拜官能基是從第一當量的醯基衍生而來,與作為氧接受者的第二當量的醯基反應以產生羧基基團。
第二章講述鉻、鉬、鎢等雙金屬多重鍵錯合物的製備。在此,我們合成出一個新穎的NNPtBu2三牙配基,此配基特點為擁有節外生枝的磷原子團。透過使用這個NNPtBu2配基,成功合成並鑑定出鉻(1+)-鉻(1+)四重鍵錯合物 [Cr2(µ-κ2-N-2,6-iPr2C6H3-C5H3N-PtBu2)2] (30)、甲苯配位的雙鉬錯合物 [Mo2(µ-η2-2,3:η2-5,6-C6H5CH3)(µ-κ2-N-2,6-iPr2C6H3-C5H3N-PtBu2)2] (32)、和一個鎢(2+)-鎢(3+)混價錯合物 [W2(µ-Cl)(Cl2)(µ-κ2-N-2,6-iPr2C6H3-C5H3N-PtBu2)2] (33)。
第三章中將進入新製備的雙鉻金屬五重鍵錯合物(30)的反應性的討論。在這裡我們嘗試利用錯合物 30 催化部分在有機反應常被需要的反應(例如:吡啶的硼氫化反應與碳氫鍵活化反應; 碳鋅化以及(sp3)碳-硫鍵活化反應)。透過與吡啶硼烷試劑(C5H5N·BH3, 2-Me-C5H4N·BH3, 4-Me-C5H4N·BH3)反應我們能夠製備{Cr2(µ-κ2-(N-2,6-iPr2C6H3-C5H3N-PtBu2)]2(4-RC5H5NBH2)} (R = H (36), R = Me (37)), {Cr2(µ-κ2-(N-2,6-iPr2C6H3-C5H3N-PtBu2)]2(2-CH3C5H5NBH2)}R = Me, R’ = H (38)。 此外,吡啶硼烷試劑與雙氮基眯配位基配味的雙鉻金屬五重鍵錯合物[Cr2(μ-κ2-HC(N-2,6-iPr2C6H3)2)2] (24)反應我們能夠製備錯合物吡啶碳氫鍵活化雙鉻金屬四重鍵錯合物[Cr2(µ-κ2-HC(N-2,6-iPr2C6H3)2(µ-H)C5H4NBH3] (39)。錯合物 30 與二苯基鋅能夠進行碳鋅化反應形成錯合物cis-(µ-ZnC6H5)(η1-C6H5)[Mo2(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (32),最後能夠在與二甲基硫的反應中獲得(sp3)碳-硫鍵活化的錯合物trans-(µ-SMe)2[µ-κ2-Cr(N-2,6-iPr2C6H3-C5H3N-PtBu2)]2 (41)。
第四章在描述兩種由六牙配基bis(pyridylamido)amidinate構成六銅(1+)線型單體錯合物再經由ligand-unsupported cuprophilicity形成十二銅(1+)擴展金屬鍊[Cu6(μ6-κ6-BPAAAr)2]2 (522: Ar = Dmp; 532: Ar = Mes) 的製備方法以及特性解析。此外,三個至六個銅(1+)金屬鍊也被合成鑑定出來。基於X光單晶繞射分析的結果,522 和 532中的兩個六銅(1+)線型單體錯合物為彎曲結構,並且銅和銅之間有鍵結。透過拉曼光譜亦能證實兩個線型單體錯合物之間有ligand-unsupported 銅(1+)-銅(1+)鍵。DFT理論計算得出微弱的軌域吸引作用力導致ligand-unsupported cuprophilicity的現象,作用力大約為2.4 kcal/mol。
This dissertation describes the synthesis and reactivity studies of quintuply bonded group VI metal complexes. Additionally, several copper(I) extended metal atom chains (EMACs) are prepared by using multi-nitrogen donor ligands. For well understanding, this thesis is divided into four chapters.
The first chapter describes the facile haloacylation of quintuply bonded dimolybdenum amidinate [Mo2(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (1). Reaction of 1 with various acyl halides resulted in the formation of β-halo-α,β-quadruply-bonded dimolybdenum acyl complexes anti-Mo2(X)(μ-κ2-OCR)[μ-κ2-HC(N-2,6-iPr2C6H3)2]2 (R = Me, X= Cl (3); R = C6H5, X = Cl (4), Br (5); R= 4-FC6H4, X= Cl (6); R = 2-MeC6H4, X = Cl (7)). By performing DFT calculations on Mo2(Cl)(μ-κ2-OCMe)[μ-κ2-HC(N-2,6-iPr2C6H3)2]2 suggested that it equilibrates with the oxo-alkylidyne Mo2(O)(μ-Cl)(μ-CMe)[μ-κ2-HC(N-2,6-iPr2C6H3)2]2 in a ratio of about 100:1. The nucleophilic Mo=O functionality turned out to be reactive towards several electrophiles. Complexes 3-7 were then further treated with another one equiv of acyl halides RC(O)X to undergo haloacylation and yielded alkylidyne-bridged dimolybdenum species [Mo2(X)(µ-X)(µ-CR)(κ2-O2CR)(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (R = Me, X = Cl (10); R = C6H5, X = Cl (11), Br (12); R = 4-FC6H4, X = Cl (13); R = 2-MeC6H4, X = Cl (14)). To understand the formation of oxo-alkylidyne functionalities, reactions of 4 with N-methylbenzimidoyl chloride and diphenylphoshinic chloride were performed and yielded two benzylidyne species Mo2(Cl)(µ-Cl)(µ-CC6H5)(κ2-ONCH3C6H5)(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (17) and [Mo2(Cl)(µ-Cl)(µ-CC6H5)(κ2-O2PPh2)(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (18). These results clearly indicated that the carbyne groups were derived from the first equivalent of acyl group and the second acyl group served as an oxygen acceptor to give the carboxylato group.
The second chapter shows the preparation of Cr, Mo and W metal-metal multiply bonded bimetallic units. Herein, we synthesized a novel tridentate NNPtBu2 ligand which features a pendent phosphorous atom in the supporting ligand. By using this NNPtBu2 ligand, a Cr(I)-Cr(I) quintuple bond complex [Cr2(µ-κ2-N-2,6-iPr2C6H3-C5H3N-PtBu2)2] (30), toluene coordinated Mo-Mo complex [Mo2(µ-η2-2,3:η2-5,6-C6H5CH3)(µ-κ2-N-2,6-iPr2C6H3-C5H3N-PtBu2)2] (32), and a mix-valent W(II)-W(III) species [W2(µ-Cl)(Cl2)(µ-κ2-N-2,6-iPr2C6H3-C5H3N-PtBu2)2] (33) were successfully isolated and completely characterized.
The third chapter deals with the reactivity studies of newly prepared dichromium quintuply bonded complex (30). Herein, the performed reactions (hydroboration of pyridine, C-H bond activation of pyridine, carbozincation and C(sp3)-S activation) are similar to the widely used reactions in organic chemistry. Upon addition of pyridyl boranes (C5H5N·BH3, 2-Me-C5H4N·BH3, 4-Me-C5H4N·BH3) on 30 produced {Cr2(µ-κ2-(N-2,6-iPr2C6H3-C5H3N-PtBu2)]2(4-RC5H5NBH2)} (R = H (36), R = Me (37)), {Cr2(µ-κ2-(N-2,6-iPr2C6H3-C5H3N-PtBu2)]2(2-CH3C5H5NBH2)}R = Me, R’ = H (38). In addition, reaction of pyridyl borane with NCN supported quintuple bonded complex [Cr2(μ-κ2-HC(N-2,6-iPr2C6H3)2)2] (24) yielded a C-H bond activated pyridine dichromium quadruply bonded complex [Cr2(µ-κ2-HC(N-2,6-iPr2C6H3)2(µ-H)C5H4NBH3] (39). Furthermore, complex 30 underwent carbozincation with Ph2Zn and gave an anti-(µ-ZnC6H5)(η1-C6H5)[µ-κ2-Cr(N-2,6-iPr2C6H3-C5H3N-PtBu2)]2 (40) which is in contrast to the prepared cis-(µ-ZnC6H5)(η1-C6H5)[Mo2(µ-κ2-HC(N-2,6-iPr2C6H3)2)2] (32) in terms of structural features. Also, complex 30 has an ability to activate C(sp3)-S bond upon reaction of dimethyl sulfide and produced a trans-(µ-SMe)2[µ-κ2-Cr(N-2,6-iPr2C6H3-C5H3N-PtBu2)]2 (41).
The fourth chapter describes the synthesis and characterization of two dodecacopper(I) EMACs [Cu6(μ6-κ6-BPAAAr)2]2 (522: Ar = Dmp; 532: Ar = Mes) constructed by two hexadentate bis(pyridylamido)amidinate-supported hexacopper(I) string complexes (monomers) via the ligand-unsupported cuprophilicity. In addition, 3-6 copper(I) atom chains were also synthesized and characterized. Based on X-ray crystallography, the two hexacopper(I) fragments in 522 and 532 show a bent conformation with short unsupported Cu-Cu contacts. Furthermore, the observed short ligand-unsupported Cu(I)-Cu(I) contacts were confirmed by Raman spectroscopy. DFT calculations indicate the ligand-unsupported cuprophilicity derive from weak attractive orbital interactions, and the strength is estimated to be 2.4 kcal/mol.
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