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研究生：	翁語喬 Wong, Yu-chiau
論文名稱：	鉛二價化合物在多硫配位基下的合成、結構與鑑定 Syntheses, Structures, and Characterizations of Lead(II) Complexes in A Sulfur-rich Ligated Environment
指導教授：	許鏵芬 Hsu, Hua-fen
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：	2008
畢業學年度：	96
語文別：	英文
論文頁數：	114
中文關鍵詞：	鉛、烷基硫、Pb-207 核磁共振光譜
外文關鍵詞：	Pb, thiolate, 207Pb NMR
相關次數：	點閱：95 下載：2
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鉛是一種潛藏在環境中並且帶有毒性的金屬，而鉛的配位化學已經受到重視並且被廣泛的研究。從研究中發現鉛會和生物體中含有很多半胱胺酸(Cysteine, Cys)的物質結合。因此，促使我們合成了一系列類似半胱胺酸(Cysteine, Cys)的配位基─烷基硫(thiolate)。這些配位基包括了PS3、PS3’、PS3’’、PhPS2’’、tBuPS2”以及PhPS1”。我們利用這些配位基去與Pb二價的金屬作反應並且探討其化學性質。
在本論文中，[N(CH3)3(PhCH2)][Pb(PS3)] (1)、[N(C7H15)4][Pb(PS3’)] (2)、[N(C2H5)4][Pb(PS3”)] (3a及3b)、[Pb(PhPS2”)](4)、[Pb(tBuPS2”)](5)以及[Pb(PhPS1”)](6)這七種化合物已經成功的被合成出來。化合物1~6的結構已由X-ray繞射儀器所鑑定。其中，在固態下，化合物1、3b、4、5以及6都因為有分子間作用力(intermolecular interaction)而形成一維的鏈狀(one dimensional chain)或是類似二聚體(dimeric-like)的結構。此外我們也利用元素分析(EA, Elemental Analysis)、紅外光吸收光譜(infrared spectroscopy)、紫外光可見光光譜(ultraviolet-visible Spectroscopy)以及核磁共振光譜(nucleic magnetic resonance spectroscopy)去鑑定化合物1、2、3、4以及6。最後我們使用了Pb-207核磁共振光譜(207Pb NMR)去推論在溶液的狀態下化合物1以及3b並沒有分子間作用力，而化合物4以及6有分子間作用力。

Pb(II) chemistry has drawn much attention due to toxicity and occurrence of this metal ion in the environment. Lead can interact with some biological molecules that contain cysteine residue. Therefore, we are motivated to explore the chemistry of lead(II) ion interacting with Cys-like ligands, thiolates, such as tribenzenethiolate, bisbenzenethiolate, and benzenethiolate (PS3, PS3’, PS3’’, PhPS2’’, tBuPS2”, and PhPS1”).
In this research, seven Pb(II) complexes have been synthesized and characterized. They are [N(CH3)3(PhCH2)][Pb(PS3)] (1), [N(C7H15)4]- [Pb(PS3’)] (2), [N(C2H5)4][Pb(PS3”)] (3a and 3b), [Pb(PhPS2”)] (4), [Pb(tBuPS2”)] (5), and [Pb(PhPS1”)] (6). The structures of 1-6 were determined by X-ray diffraction. The data show that 1, 3b, 4, 5, and 6 have intermolecular interactions, leading to one-dimensional chain or dimer-like structure in the solid state. According to 207Pb NMR studies, the intermolecular interaction is absent in 1 and 3b in solution state, but present in 4 and 6. In addition, elemental analysis, infrared spectroscopy, ultraviolet-visible spectroscopy, 31P NMR, and 1H NMR were also used to characterize these complexes.

Abstract in Chinese                                              i
Abstract                                                      ii
Acknowledgement                                             iii
Contents                                                      v
List of Schemes                                                x
List of Figures                                                 xi
List of Tables                                                 xiv

Chapter 1 General Introduction
1.1 Introduction                                                1
1.2 Lead in the Biological systems                                  1
1.2.1 The Effect of Lead Poising in the Plants                       1
1.2.2 The Effect of Lead Poising in the Humans                    3
1.3 Stereochemistry of Pb-complexes: Holo-directed and Hemi-directed Coordination                                                5
1.4 Discussion of the Reference and Motivation                       6

Chapter 2 Experiments
2.1 Materials and Syntheses                                      10
2.1.1 Synthesis of [N(CH3)3(CH2Ph)][Pb(PS3)] (1)                 12
2.1.2 Synthesis of [N(C7H15)4][Pb(PS3’)] (2)                     12
2.1.3 Synthesis of [N(C2H5)4][PbPS3”] (3a) and [N(C2H5)4][Pb(PS3”)]
(3b)                                                 13
2.1.4 Synthesis of [Pb(PhPS2”)] (4)                             14
2.1.5 Synthesis of [Pb(tBuPS2”)] (5)                             14
2.1.6 Synthesis of [Pb(PhPS1”)] (6)                             15
2.2 Single Crystal X-ray Structure Determination                     15
2.3 Characterizations with Elemental Analysis                       16
2.4 Characterizations with Infrared Spectroscopy                     16
2.5 Characterizations with Ultraviolet-Visible Spectroscopy            16
2.6 Characterizations with Nucleic Magnetic Resonance Spectroscopy    16
2.6.1 207Pb NMR                                            17
2.6.2 31P NMR                                             18
2.6.3 1H NMR                                              18

Chapter 3 Result and discussion
3.1 Synthesis, Structure, and Spectra of [N(CH3)3(CH2Ph)][Pb(PS3)] (1)
                                                         19
3.1.1 Synthesis and Crystal Structure of [N(CH3)3(CH2Ph)][Pb(PS3)] (1)
                                                         19
3.1.2 Infrared Spectra of [N(CH3)3(CH2Ph)][Pb(PS3)] (1)           23
3.1.3 Ultraviolet-Visible Spectra of [N(CH3)3(CH2Ph)][Pb(PS3)] 
(1)                                                   23
3.1.4 Nucleic Magnetic Resonance Spectra of [N(CH3)3(CH2Ph)][Pb(PS3)] (1)                                                  25
(A) 207Pb NMR                                           25
(B) 31P NMR                                             26
3.2 Synthesis, structure, and spectra of [N(C7H15)4][Pb(PS3’)] (2)        27
3.2.1 Synthesis and X-ray Diffraction of [N(C7H15)4][Pb(PS3’)] (2)    27
3.2.2 Infrared Spectra of [N(C7H15)4][Pb(PS3’)] (2)                30
3.2.3 Ultraviolet-Visible Spectra of [N(C7H15)4][Pb(PS3’)] (2)        30
3.2.4 Nucleic Magnetic Resonance Spectra of [N(C7H15)4][Pb(PS3’)] (2)
                                                     32
(A) 207Pb NMR                                            32
(B) 31P NMR                                              33
3.3 Synthesis of [N(C2H5)4][Pb(PS3”)] (3a) and [N(C2H5)4][Pb(PS3”)] (3b)
                                                         34
3.3.1 Synthesis                                             34
3.3.2 Crystal Structure of [N(C2H5)4][Pb(PS3”)] (3a)               34
3.3.3 Crystal Structure of [N(C2H5)4][Pb(PS3”)] (3b)               37
3.3.4 Infrared Spectra of [N(C2H5)4][Pb(PS3”)] (3a) and [N(C2H5)4][Pb(PS3”)] (3b)                               41
3.3.5 Ultraviolet-Visible Spectra of [N(C2H5)4][Pb(PS3”)] (3a) and [N(C2H5)4][Pb(PS3”)] (3b)                               42
3.3.6 Nucleic Magnetic Resonance Spectra of [N(C2H5)4][Pb(PS3”)] (3a) and [N(C2H5)4][Pb(PS3”)] (3b)
                                                    43
(A) 207Pb NMR                                            43
(B) 31P NMR                                              44
3.4 Synthesis, Structure, and Spectra of [Pb(PhPS2”)] (4)               46
3.4.1 Synthesis and Crystal Structure of [Pb(PhPS2”)] (4)            46
3.4.2 Infrared Spectra of [Pb(PhPS2”)] (4)                        49
3.4.3 Ultraviolet-Visible Spectra of [Pb(PhPS2”)] (4)                50
3.4.4 Nucleic Magnetic Resonance Spectra of [Pb(PhPS2”)] (4)
                                                    51
(A) 207Pb NMR                                            51
(B) 31P NMR                                              52
3.5 Synthesis, Structure, and Spectra of [Pb(tBuPS2”)] (5)               53
3.5.1 Syntheses and Crystal Structure of [Pb(tBuPS2”)] (5)           53
3.6 Synthesis, Structure, and Spectra of [Pb(PhPS1”)] (6)               57
3.6.1 Syntheses and Crystal structure of [Pb(PhPS1”)] (6)            57
3.6.2 Infrared Spectra of [Pb(PhPS1”)] (6)                        61
3.6.3 Ultraviolet-Visible Spectra of [Pb(PhPS1”)] (6)                61
3.6.4 Nucleic Magnetic Resonance Spectra of [Pb(PhPS1”)] (6)
                                                    62
(A) 207Pb NMR                                            62
(B) 31P NMR                                              63
3.7 Discussion                                                65

Chapter 4 Conclusion                                           74

Reference                                                    76
Appendix A: 1H NMR Spectrum                                  81
Appendix B: Atomic coordinates (×10–4) and isotropic displacement parameters (in Å2×10–3)                              86
Appendix C: Anisotropic displacement parameters (Å2×10–3)          101
 
                                            List of Schemes
Chapter 1 General Introduction
Scheme 1-1 Effect of Pb-poison in the plants                         2
Scheme 1-2 Structure of the cysteine and glutathione                   3
Scheme 1-3 (A) Holo-directed and (B) Hemi-directed Coordination       6
Scheme 1-4 Difference between Pb-L and Pb-lp-X of the hemi-directed and holo-directed Pb complex                               6
Scheme 1-5 Sulfur-rich ligands used in this research                   9

Chapter 4 Conclusion
Scheme 4-1 Synthesis of the complex 1~6                           75
 
                                            List of Figures
Chapter 1 General Introduction
Fig.1-1 (a) Tertiary structure of ALAD (b) Synthesis of porphobilinogen catalyst by ALAD (c) Zinc binding site of ALAD               4
Fig. 1-2 Structures isolated by (a) Philip et al. (b) Brian et al.             7
Fig. 1-3 Lead-thiolate complexes investigated by (a) Brian et al. (b) Paulo et al. (c) Sarah et al. (d) Mohan et al.                           8

Chapter 2 Experiments
Fig. 2-1 207Pb-1H heteronuclear multiple-quantum correlation spectrum of PbPh4                                                17

Chapter 3 Result and discussion
Fig. 3-1 (a) ORTEP diagram of complex 1 shown with 35% thermal ellipsoids. H atoms and cations are omitted for clarity (b) intermolecular interaction of complex 1 (c) packing diagram of complex 1 (d) one-dimensional chain of complex 1                        21
Fig. 3-2 IR spectra of [N(CH3)3(CH2Ph)][PbPS3] (1) (blue line) and PS3H3 (black line)                                            23
Fig. 3-3 UV/Vis spectrum of [N(CH3)3(CH2Ph)][PbPS3] (1) in DMF Concentration ＝ 5.61 × 10–5 mol/L                        24
Fig. 3-4 207Pb NMR spectrum of [N(CH3)3(CH2Ph)][PbPS3] (1)         25
Fig. 3-5 31P NMR spectrum of [N(CH3)3(CH2Ph)][PbPS3] (1)           26
Fig. 3-6 ORTEP diagram of complex 2 shown with 35% thermal ellipsoids. H atoms and cations are omitted for clarity                     29
Fig. 3-7 IR spectra of PS3’H3 (black line) and [N(C7H15)4][PbPS3’] (2) (blue line)                                                  30
Fig. 3-8 UV/Vis spectrum of [N(C7H15)4][PbPS3’] (2) in DMF
Concentration ＝ 3.55 × 10–5 mol/L                        31
Fig. 3-9 207Pb NMR spectrum of [N(C7H15)4][PbPS3’] (2)              32
Fig. 3-10 31P NMR spectrum of [N(C7H15)4][PbPS3’] (2)               33
Fig. 3-11 ORTEP diagram of complex 3a shown with 35% thermal ellipsoids. H atoms and cation are omitted for clarity                   36
Fig. 3-12 (a) ORTEP diagram of complex 3b shown with 35% thermal ellipsoids. H atoms and cation are omitted for clarity (b) intermolecular interaction of complex 3b (c) packing diagram of complex 3b (d) one-dimensional chain of complex 3b         40
Fig. 3-13 IR spectra of PS3”H3 (black line) and [N(C2H5)4][PbPS3”] (3) (blue line)                                                 42
Fig. 3-14 UV/Vis spectrum of [N(C2H5)4][PbPS3”] (3) in DMF
Concentration ＝ 3.08 × 10–5 mol/L                       43
Fig. 3-15 207Pb NMR spectrum of [N(C2H5)4][PbPS3”] (3)              44
Fig. 3-16 31P NMR spectrum of [N(C2H5)4][PbPS3”] (3)               45
Fig. 3-17 (a) ORTEP diagram of complex 4 shown with 35% thermal ellipsoids. H atoms are omitted for clarity (b) intermolecular interaction of complex 4 (c) packing diagram of complex 4     48
Fig. 3-18 IR spectra of PhPS2”H2 (black line) and [PbPhPS2”] (4) (blue line)
                                                    50
Fig. 3-19 UV/Vis spectrum of [PbPhPS2”] (4) in DMF
Concentration ＝ 5.32 × 10–5 mol/L                       51
Fig. 3-20 207Pb NMR spectrum of [PbPhPS2”] (4)                    52
Fig. 3-21 31P NMR spectrum of [PbPhPS2”] (4)                       52
Fig. 3-22 (a) ORTEP diagram of complex 5 shown with 35% thermal ellipsoids. H atoms are omitted for clarity (b) intermolecular interaction of complex 5 (c) packing diagram of complex 5 (d)one-dimensional chain of complex 5                     55
Fig. 3-23 (a) ORTEP diagram of complex 6 shown with 35% thermal ellipsoids. H atoms are omitted for clarity (b) intermolecular interaction of complex 6 (c) packing diagram of complex 6     59
Fig. 3-24 IR spectra of PhPS1”H (black line) and [PbPhPS1”](6) (blue line)
                                                    61
Fig. 3-25 UV/Vis spectrum of [PbPhPS1”](6) in CH2Cl2
Concentration ＝ 7.67 × 10–5 mol/L                       62
Fig. 3-26 207Pb NMR spectrum of [PbPhPS1”](6)                      63
Fig. 3-27 31P NMR spectrum of [PbPhPS1”](6)                       64
Fig. 3-28 UV/Vis spectra of complexes 1, 2, 3, 4, and 6                67
Fig. 3-29 207Pb NMR spectra of complexes 1, 2, 3, 4, and 6             70
Fig. 3-30 1H NMR spectrum of complex 6                          71
 
                                               List of Table
Chapter 2 Experiments
Table 2-1 Material used in this research                             10

Chapter 3 Result and discussion
Table 3-1 Crystal data and refinement parameters for complex 1         20
Table 3-2 Selected bond lengths (Å) and bond angles (deg) for complex 1 
                                                    22
Table 3-3 Crystal data and refinement parameters for complex 2         28
Table 3-4 Selected bond lengths (Å) and bond angles (deg) for complex 2
                                                            29
Table 3-5 Crystal data and refinement parameters for complex 3a        35
Table 3-6 Selected bond lengths (Å) and bond angles (deg) for complex 3a
                                                            37
Table 3-7 Crystal data and refinement parameters for complex 3b        39
Table 3-8 Selected bond lengths (Å) and bond angles (deg) for complex 3b
                                                            41
Table 3-9 Crystal data and refinement parameters for complex 4         47
Table 3-10 Selected bond lengths (Å) and bond angles (deg) for complex 4
                                                            49
Table 3-11 Crystal data and refinement parameters for complex 5        54
Table 3-12 Selected bond lengths (Å) and bond angles (deg) for complex 5
                                                            56
Table 3-13 Crystal data and refinement parameters for complex 6        58
Table 3-14 Selected bond lengths (Å) and bond angles (deg) for complex 6
                                                            60
Table 3-15 The average bond lengths of Pb-S and Pb-P for complex 1~6
                                                            65
Table 3-16 The average bond lengths and coupling constant of Pb-P for complexes 1, 2, 3, 4, and 6                              66
Table 3-17 Summaries of the chemical shifts of 207Pb NMR of Pb complexes
                                                   72
                                    

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