雙鉻五重鍵錯合物的合成與化性研究｜國立清華大學博碩士論文庫

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研究生：	顏君旭 Yen, Chun-Hsu
論文名稱：	雙鉻五重鍵錯合物的合成與化性研究 Chemistry of Quintuply-Bonded Dichromium Complexes: Activation, Cleavage, Complexation and Dimerization
指導教授：	蔡易州 Tsai, Yi-Chou
口試委員:
學位類別：	碩士 Master
系所名稱：	理學院 - 化學系 Department of Chemistry
論文出版年：	2009
畢業學年度：	97
語文別：	中文
論文頁數：	171
中文關鍵詞：	雙鉻、五重鍵
外文關鍵詞：	quintuply-bonded, dichromium complex, activation, cleavage, complexation, dimerization
相關次數：	點閱：108 下載：0
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還原錯合物Cr2(□-Cl)2[□-NC(H)N]Dep2(THF)2 (2b) 能得到三轉軸、鍵級為4.5的錯合物 Cr2[□-NC(H)N]Dep3 (4)，進一步還原則能得到五重鍵雙鉻錯合物Cr2[□-NC(H)N]Dep3‾ (5)。另外，低價數、低配位數的雙鉻五重鍵錯合物Cr2[□-NC(H)N]Dipp2 (3c) 與醋酸鉀反應得到負一價電荷之五重鍵雙鉻錯合物(□-CH3COO)Cr2[□-NC(H)N]Dipp2‾ (6)；若是將3c與炔類分子如3-己炔、二苯乙炔或1-戊烷反應，則分別得到(□-□1:□1-CH3CH2CCCH2CH3)Cr2[□-NC(H)N]Dipp2 (7)、(□-□1:□1-PhCCPh) Cr2[□-NC(H)N]Dipp2 (8)及(□-□1:□1-CH3(CH2)2CCH)Cr2[□-NC(H)N]Dipp2 (9) 等非典型三轉軸四重鍵雙鉻錯合物；錯合物3c甚至能對末端炔進行三聚合環化反應。除此之外，錯合物3c與共軛雙烯如1,3-環己二烯生成(□-□2:□2-C6H8)Cr2[□-NC(H)N]Dipp2 (10)之扭曲風車型四重鍵錯合物，但與異員環共軛雙烯如呋喃分子則會形成單核二價錯合物Cr[NC(H)N]Dipp2(11a)。若換成立體阻礙較小的錯合物Cr2[□- NC(H)N]Dep2 (3b)與呋喃分子反應則進行特殊的雙聚合反應而生成{Cr2[□-NC(H)N]Dep2}2 (12)。
雙鉻五重鍵錯合物對含氮官能基的小分子亦有許多特殊反應：錯合物3c能將偶氮苯進行還原斷裂而得到(□-PhN)2(□1-PhN)2Cr2 [NC(H)N]Dipp2 (13)；結構類似地，3c與有機疊氮如對甲基苯疊氮生成錯合物(□-p-tolylN)2(□1-p-tolylN)2Cr2[NC(H)N]Dipp2 (14)，若與立障較大的有機疊氮如三甲基矽烷疊氮及1-金剛烷基疊氮則分別得到錯合物(□-TMSN)(□-N)Cr[□-NC(H)N]Dipp(□1-TMSN)Cr[□2-NC(H)N]Dipp (15)及(□-AdN)2[□□- NC(H)N]DippCr(□□-AdN)Cr[□□-NC(H)N]Dipp (16)。3c與疊氮化鈉反應則會生成{(□-N)[□□-NC(H)N]DippCr[□-□□□□□-NC(H)N]Dipp Cr}22- (17)。立體阻礙較小的錯合物3b與白磷分子反應能得到錯合物(□-□4:□4-P4)(Cr2[□-NC(H)N]Dep2)2 (18)；而錯合物3c與白磷分子反應則得到(□-□1:□1-P4)Cr2[□-NC(H)N]Dipp2 (19a)，過量的錯合物3c與白磷分子反應則需要鋰離子支持產物的結構，因而得到四鉻四磷立方中心錯合物{(□-P)2Cr2[□- NC(H)N]DippLi}2 (19b)。
3c通入一氧化二氮以提供氧原子來源，得到錯合物(□- □□□[□-NC(H)N]DippCr2[□2-NC(H)N]Dipp2 (20)；若與雙硫鍵雙硒鍵如雙苯二硫醚及雙苯二硒醚反應，則將雙硫、雙硒鍵打斷而分別生成[□2- NC(H)N]DippCr(□-PhS)3Cr(□-PhS)3Cr[□2-NC(H)N]Dipp (21)及(□-PhSe)3 [□2-NC(H)N]Dipp2Cr2 (22)。除此之外，3c與硫粉反應能得到主要產物(□-□2:□1-S2)2{(□-□2:□2-S2)Cr2[□2-SNC(H)N]Dipp2}(Cr[□2-NC(H)N]Dipp) (23)、及次要產物(□-S)2(□2-S2)2Cr2[□-NC(H) N]Dipp2 (24)；另將3c與硒粉反應得到三核鉻錯合物(□-Se2)2(□-Se4)Cr3[□2-NC(H)N]Dipp3 (25)。
利用錯合物3c與吡啶-氮-氧化物反應，會釋出氫氣而得到碳-氫鍵活化錯合物(□-□□O:□□o-C-PyO)(□-O)(□-OH){(□2-biPy)Cr[□1- NC(H)N]Dipp}{(□1-PyO)Cr[□2-NC(H)N]Dipp}(26)；若3c與苯乙腈反應則能得到些微活化碳-氮三鍵之錯合物(□-□□C:□□N-PhCN)2(□□-PhCN)2 Cr2[□-NC(H)N]Dipp2 (27)。當3c通入過量一氧化碳時，則進行CO插入反應而得到碳-氧雙鍵稍被活化，且需鋰離子支持結構之錯合物{(□-□□C:□□O-CO)[□2-C(O)NC(H)N]DippCr(CO)3Li(OEt)2}2(28)。再者，立體阻礙較小的雙鉻五重鍵錯合物3b與取代的呋喃分子如2-甲基呋喃及2,5-雙甲基呋喃分子反應時則分別得到取代的呋喃分子之碳-氧鍵斷裂、開環的結果：{Cr[□1-NC(H)N]Dep(□-OCH(Me)CH2CH2CH2)[□- NC(H)N]DepCr}2 (29a)與{Cr[□1-NC(H)N]Dep[□-OCH(Me)CH2CH2CH (Me)][□-NC(H)N]DepCr}2 (29b)。最後，3b與反應性極低的六氟苯反應則能得到(□-F)[□-NC(H)N]Dep2Cr(Et2O)Cr(□1-C6F5) (30)，碳-氟鍵斷裂的結果。

中文摘要 ---------------------------------------------------------I
Abstract ---------------------------------------------------------III
謝誌-------------------------------------------------------------V
目錄-------------------------------------------------------------VII
圖目錄-----------------------------------------------------------XI
流程圖目錄-----------------------------------------------------XIII
第一章 緒論-------------------------------------------------------1
  1. 金屬多重鍵的發展--------------------------------------------1
2. 小分子的活化反應--------------------------------------------8
2-1. 鈮氮丙啶氫化物(Niobaziridine-Hydride)官能團的小分子活化--------8
2-2. 反三明治(Inverted-Sandwich)雙鉻、雙釩錯合物的小分子活化--------9
2-3. 低配位氫化物鐵(Low-Coordinate Iron-Hydride)錯合物的小分子活化-10
2-4. 雙亞胺吡啶(Bis(imino)pyridine)單核鐵錯合物的小分子活化--------11
2-5. 雙鉻五重鍵錯合物的小分子活化-------------------------------12

第二章  雙鉻三轉軸錯合物之結構探討----------------------13
  1. 前言--------------------------------------------------------13
  2. 燈籠型三轉軸錯合物的合成與研究--------------------------14
2-1. Cr2(□-Cl)2[□-NC(H)N]Dep2(THF)2 (2b)與Cr2[□-NC(H)N]Dep3 (4) 錯合物的合成與鑑定--------------------------------------------------14
3. 配基不對稱之燈籠型三轉軸錯合物的合成與研究------------18
    3-1. 前言-------------------------------------------------------18
3-2. 錯合物{K(cryptand[2.2.2])}(□-CH3COO)Cr2[□-NC(H)N]Dipp2 (6)的合成與鑑定-------------------------------------------------------20
3-3. 錯合物(□-□1:□1-CH3CH2CCCH2CH3)Cr2[□-NC(H)N]Dipp2 (7)的合成與鑑定---------------------------------------------------------23
3-4. 錯合物(□-□1:□1- PhCCPh)Cr2[□-NC(H)N]Dipp2 (8) 的合成與鑑定-----25
3-5. 錯合物(□-□1:□1-CH3(CH2)2CCH)Cr2[□-NC(H)N]Dipp2 (9)的合成與鑑定
----------------------------------------------------------27
3-6. 錯合物(□-□2:□2-C6H8)Cr2[□-NC(H)N]Dipp2 (10)的合成與鑑定--------30
4. 雙鉻五重鍵雙聚合反應的探討與研究------------------------32
4-1. 錯合物 Cr[NC(H)N]Dipp2(11a)的合成與鑑定----------------------32
4-2. 錯合物 Cr2[□-NC(H)N]Dep2 (3b)的合成與鑑定--------------------33
4-3. 錯合物 {Cr2[□-NC(H)N]Dep2}2 (12)的合成與鑑定-----------------34
5. 結論--------------------------------------------------------38

第三章  雙鉻五重鍵錯合物活化小分子之反應性探討------40
  1. 前言--------------------------------------------------------40
2. 雙鉻五重鍵與第十五族含氮小分子之活化反應--------------40
2-1. 前言-------------------------------------------------------40
2-2. (□-PhN)2(□□-PhN)2Cr2[NC(H)N]Dipp2 (13)錯合物的合成與鑑定-------41
2-3. (□-p-tolylN)2(□□-p-tolylN)2Cr2[NC(H)N]Dipp2 (14)錯合物的合成與鑑定-43
2-4. (□-TMSN)(□-N)Cr[□-NC(H)N]Dipp(□□-TMSN)Cr[□□-NC(H)N]Dipp (15) 錯合物的合成與鑑定----------------------------------------------46
2-5. (□-AdN)2[□□-NC(H)N]DippCr(□□-AdN)Cr[□□-NC(H)N]Dipp (16) 錯合物的合成與鑑定----------------------------------------------------50
2-6. {(□-N)[□□-NC(H)N]DippCr[□-□□□□□-NC(H)N]DippCr}2 (17) 錯合物的合成與鑑定--------------------------------------------------------53
2-7. 小結-------------------------------------------------------55
3. 雙鉻五重鍵與第十五族之白磷的活化反應-------------------55
    3-1. 前言-------------------------------------------------------55
    3-2. (□-□4:□4-P4)(Cr2[□-NC(H)N]Dep2)2 (18)錯合物的合成與鑑定----------56
3-3. (□-□1:□1-P4)Cr2[□-NC(H)N]Dipp2 (19a)錯合物的合成與鑑定----------58
 3-4. {(□-P)2Cr2[□-NC(H)N]DippLi}2 (19b)錯合物的合成與鑑定-----------61
 3-5. 小結-------------------------------------------------------65
4. 雙鉻五重鍵與第十六族之小分子的活化反應-----------------66
 4-1. 前言-------------------------------------------------------66
 4-2. (□-□□□[□-NC(H)N]DippCr2[□2-NC(H)N]Dipp2 (20) 錯合物的合成與鑑定-67
    4-3. [□2-NC(H)N]DippCr(□-PhS)3Cr(□-PhS)3Cr[□2-NC(H)N]Dipp (21)錯合物的合成與鑑定----------------------------------------------------70
    4-4. (□-PhSe)3[□2-NC(H)N]Dipp2Cr2 (22)錯合物的合成與鑑定------------72
 4-5. (□-□2:□1-S2)2{(□-□2:□2-S2)Cr2[□2-SNC(H)N]Dipp2}(Cr[□2-NC(H)N]Dipp) (23)與(□-S)2(□2-S2)2Cr2[□-NC(H)N]Dipp2 (24) 錯合物的合成與鑑定-------74
4-6. (□-Se2)2(□-Se4)Cr3[□2-NC(H)N]Dipp3 (25)錯合物的合成與鑑定--------78
4-7. 錯合物 3c 與錯合物 3b 與碲粉 (tellurium) 的反應--------------81
4-8. 小結-------------------------------------------------------82
5. 結論--------------------------------------------------------82

第四章  雙鉻五重鍵錯合物活化C-X (X = H、N、O、F) 之
        反應性探討------------------------------------------84
1. 前言--------------------------------------------------------84
2. 雙鉻五重鍵錯合物與氮-氧化物(N-oxide)的反應性探討-------85
2-1. 前言-------------------------------------------------------85
2-2. (□-□□O:□□o-C-PyO)(□-O)(□-OH){(□2-biPy)Cr[□1-NC(H)N]Dipp}{(□1-PyO)
Cr[□2-NC(H)N]Dipp}(26)的合成與鑑定----------------------------86
2-3. 錯合物 3c 與其他吡啶-氮-氧化物反應-------------------------89
3. 雙鉻五重鍵錯合物與R-CN反應性的探討--------------------90
3-1. 前言-------------------------------------------------------90
3-2. (□-□□C:□□N-PhCN)2(□□-PhCN)2Cr2[□-NC(H)N]Dipp2 (27)的合成與鑑定--91
3-3. 錯合物 3c 與其他腈類化合物反應-----------------------------93
4. 雙鉻五重鍵錯合物與一氧化碳及活化C-O鍵反應性的探討---93
4-1. 前言-------------------------------------------------------93
4-2.{(□-□□C:□□O-CO)[□2-C(O)NC(H)N]DippCr(CO)3Li(OEt)2}2 錯合物 (28) 的合成與鑑定--------------------------------------------------95
4-3. {Cr[□1-NC(H)N]Dep(□-OCH(Me)CH2CH2CH2)[□-NC(H)N]DepCr}2  (29a)    與{Cr[□1-NC(H)N]Dep[□-OCH(Me)CH2CH2CH(Me)][□-NC(H)N]DepCr}2 (29b) 的合成與鑑定------------------------------------------97
5. 雙鉻五重鍵錯合物活化C-F鍵的反應性探討-----------------102
5-1. 前言------------------------------------------------------102
5-2. (□-F)[□-NC(H)N]Dep2Cr(Et2O)Cr(□1-C6F5) (30)的合成與鑑定--------103
6. 結論-------------------------------------------------------106

第五章  實驗步驟與晶體結構資料-------------------------107
1. 總綱-------------------------------------------------------107
1-1. 實驗使用儀器----------------------------------------------107
1-2. 實驗溶劑與藥品--------------------------------------------108
2. 實驗步驟--------------------------------------------------110
    2-1. Cr2(□-Cl)2[□-NC(H)N]Dep2(THF)2  (2b) 的合成-------------------110
    2-2. Cr2[□-NC(H)N]Dep3  (4) 的合成--------------------------------110
    2-3. Cr2(□-Cl)2[□-NC(H)N]Dipp2(THF)2  (2c) 的合成-------------------111
    2-4. Cr2[□-NC(H)N]Dipp2  (3c) 的合成------------------------------111
    2-5. {K(cryptand[2.2.2])}(□-CH3COO)Cr2[□-NC(H)N]Dipp2  (6) 的合成---112
    2-6. (□-□1:□1-CH3CH2CCCH2CH3)Cr2[□-NC(H)N]Dipp2  (7) 的合成-------113
    2-7. □-□1:□1- PhCCPh)Cr2[□-NC(H)N]Dipp2  (8) 的合成----------------113
    2-8. (□-□1:□1-CH3(CH2)2CCH)Cr2[□-NC(H)N]Dipp2  (9) 的合成----------114
    2-9. (□-□2:□2-C6H8)Cr2[□-NC(H)N]Dipp2  (10) 的合成-----------------115
    2-10. Cr2[□-NC(H)N]Dep2  (3b) 的合成------------------------------116
    2-11. {Cr2[□-NC(H)N]Dep2}2  (12) 的合成---------------------------117
    2-12. (□-PhN)2(□□-PhN)2Cr2[NC(H)N]Dipp2  (13) 的合成---------------118
    2-13. (□-p-tolylN)2(□□-p-tolylN)2Cr2[NC(H)N]Dipp2  (14) 的合成--------119
    2-14. (□-TMSN)(□-N)Cr[□-NC(H)N]Dipp(□□-TMSN)Cr[□□-NC(H)N]Dipp (15) 的合成------------------------------------------------------120
    2-15. (□-AdN)2[□□-NC(H)N]DippCr(□□-AdN)Cr[□□-NC(H)N]Dipp  (16) 的合成----------------------------------------------------------120
    2-16. {(□-N)[□□-NC(H)N]Dipp Cr[□-□□□□□-NC(H)N]DippCr}2  (17) 的合成--121
    2-17. (□-□4:□4-P4)(Cr2[□-NC(H)N]Dep2)2 (18) 的合成-------------------121
    2-18. (□-□1:□1-P4)Cr2[□-NC(H)N]Dipp2  (19a) 的合成------------------122
    2-19. {(□-P)2Cr2[□-NC(H)N]DippLi}2 (19b) 的合成--------------------123
    2-20. (□-□□□[□-NC(H)N]DippCr2[□2-NC(H)N]Dipp2  (20)的合成-----------123
    2-21. [□2-NC(H)N]DippCr(□-PhS)3Cr(□-PhS)3Cr[□2-NC(H)N]Dipp (21)的合成124
    2-22. (□-PhS)3[□2-NC(H)N]Dipp2Cr2  (22) 的合成---------------------124
    2-23. (□-□2:□1-S2)2{(□-□2:□2-S2)Cr2[□2-SNC(H)N]Dipp2}(Cr[□2-NC(H)N]Dipp) (23) 的合成---------------------------------------------------125
    2-24. (□-S)2(□2-S2)2Cr2[□-NC(H)N]Dipp2 (24) 的合成-------------------125
    2-25. (□-Se2)2(□-Se4)Cr3[□2-NC(H)N]Dipp3 (25) 的合成-----------------126
    2-26. (□-□□O:□□o-C-PyO)(□-O)(□-OH){(□2-biPy)Cr[□1-NC(H)N]Dipp}{(□1-PyO)
Cr[□2-NC(H)N]Dipp} (26) 的合成-----------------------------126
    2-27. (□-□□C:□□N-PhCN)2(□□-PhCN)2Cr2[□-NC(H)N]Dipp2  (27) 的合成----127
    2-28.{(□-□□C:□□O-CO)[□2-C(O)NC(H)N]DippCr(CO)3Li(OEt)2}2 (28)的合成-------------------------------------------------------127
    2-29. {Cr[□2-NC(H)N]Dep(□-OCH(Me)CH2CH2CH2)[□-NC(H)N]DepCr}2  (29a) 的合成---------------------------------------------------128
    2-30.{Cr[□2-NC(H)N]Dep[□-OCH(Me)CH2CH2CH(Me)][□-NC(H)N]DepCr}2  (29b) 的合成----------------------------------------------128
    2-31. (□-F)[□-NC(H)N]Dep2Cr(Et2O)Cr(□1-C6F5) (30) 的合成-----------129
3. 晶體結構資料---------------------------------------------130

第六章  附錄與參考文獻------------------------------------163
1. 固態磁性資料---------------------------------------------163
    A. 錯合物Cr2[□-NC(H)N]Dipp2  (3c) 的SQUID---------------------163
    B. 錯合物(□-AdN)2[□□-NC(H)N]DippCr(□□-AdN)Cr[□□-NC(H)N]Dipp(16)的SQUID---------------------------------------------------163
    C. [□2-NC(H)N]DippCr(□-PhS)3Cr(□-PhS)3Cr[□2-NC(H)N]Dipp (21) 的SQUID ----------------------------------------------------------164
D. (□-□2:□1-S2)2{(□-□2:□2-S2)Cr2[□2-SNC(H)N]Dipp2}(Cr[□2-NC(H)N]Dipp) (23) 的SQUID--------------------------------------------------164
    E. (□-□□C:□□N-PhCN)2(□□-PhCN)2Cr2[□-NC(H)N]Dipp2  (26) 的SQUID----165
    F. {Cr[□1-NC(H)N]Dep(□-OCH(Me)CH2CH2CH2)[□-NC(H)N]DepCr}2(28)的SQUID-----------------------------------------------------165
    G. {Cr[□1-NC(H)N]Dep(□-OCH(Me)CH2CH2CH2)[□-NC(H)N]DepCr}2(29a)的
       SQUID-----------------------------------------------------166
    G. (□-F)[□-NC(H)N]Dep2Cr(Et2O)Cr(□1-C6F5)  (30) 的SQUID----------166
2. 參考文獻--------------------------------------------------167

                                

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