氨荒酸铋及黄原酸铋配合物的合成、表征及超分子结构研究
|
摘要
由于铋的无毒性、不致癌性以及铋配合物的特殊生物活性,使的铋配合物的研究受到人们的重视,经过多年的研究与发展,铋化合物已广泛的用于医学、化工以及生物等方面。同时,在主族金属元素中,铋的电子数目多、结构复杂,从而使得铋离子的配位能力强、形式多样,能与许多配体配位,形成结构新颖、性能特殊的配合物。另外,由于氨荒酸配体具有较强的配位能力,它几乎可以和所有的过渡族金属进行配位,形成螯合物,因此氨荒酸与过渡金属的配合物得到广泛的研究,例如Ni(S_2CNC_4H_8O)_2、Cu(S_2CNC_4H_8)_2、Zn(S_2CNC_4H_8O)_2、Fe(S_2CNC_4H_8O)_2(DMF)等。
目前,铋的含硫配合物的合成及结构研究也已经有较多报道,但铋的氨荒酸及黄原酸衍生物也只有少量的研究报道。本文通过氨荒酸及黄原酸配体的丰富多样的配位和连接方式,通过实验合成了具有各种结构特性的铋的氨荒酸及黄原酸配合物的晶体,通过对产物的元素分析、红外光谱和X-射线单晶衍射等分析手段,确定生成产物的性质和结构,根据产物结构推测反应的过程和形成机理,并对其自组装反应和产物的超分子结构进行了较为系统的研究。主要工作如下:
1.制得了一系列N,N-二烃基氨荒酸盐R_2NCS_2Na(R_2N= Me_2N, Et_2N, (CH_2)4N, (CH_2)5N, O(CH_2CH_2)_2N, C_6H_(12)N, Cy_2N, Bz_2N, MeN(CH_2CH_2)_2N, EtN(CH_2CH_2)_2N, BzN(CH_2CH_2)_2N)和O-烃基黄原酸盐ROCS_2Na(RO= EtO, i-PrO, i-BuO)。
2.利用硝酸铋与N, N-二烃基氨荒酸盐以及中性配体反应,合成了八种新的硝酸铋类氨荒酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,此类铋化合物一般为单核结构;N, N-二烃基氨荒酸以及中性配体均以非均性二齿形式与中心铋原子配合。从配合物Bi-S键长以及反应的条件我们可以看出,空间位阻越大,配体就越难将反应物上的硝酸根取代,硫原子与铋原子之间的配位作用就越弱,对反应条件的要求也就越高。烃基的空间位阻顺序是:N,N-二苄基> N-苄基哌嗪>哌啶。有趣的是这些配合物进一步通过分子间的C-H···S和C-H···O等弱氢键作用形成了有趣的二维网状超分子结构。
3.利用氯化铋与N, N-二烃基氨荒酸盐以及中性配体反应,合成了五种新的氯化铋类氨荒酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,N-苄基哌嗪氨荒酸盐与氯化铋反应,经过自组装反应,得到了一个34元的环状结构的超分子配位聚合物。有趣的是这些配合物进一步通过分子间的C-H···S弱氢键作用形成了一维链状或二维网状的超分子结构。
4.利用溴化铋与N, N-二烃基氨荒酸盐反应,合成了四种新的溴化铋类氨荒酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,所有配合物均通过溴桥连接成二聚体、三核的六员环或者是一维链状结构。这些化合物进一步通过分子间的C-H···S和C-H···Br等氢键作用组装成一维链状或二维网状的超分子结构。
5.利用碘化铋与N, N-二烃基氨荒酸盐以及中性配体反应,合成了九种新的碘化铋类氨荒酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,部分配合物通过碘桥连接成二聚体或者是一维链状结构。这些化合物进一步通过分子间的C-H···S和C-H···I等氢键作用组装成一维链状或二维网状的超分子结构。
6.利用卤化铋与O-烃基黄原酸盐以及中性配体反应,合成了四种新的铋类黄原酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,有中性配体参与反应形成的配合物通过π-π堆积和分子间S···S等作用,形成作用较弱的超分子一维链状结构。没有中性配体参与反应形成的配合物通过硫桥形成一维链状结构。
Due to the nontoxic characters of bismuth and pebiological activities, bismuth(III) complexes have been extensively investigated. Bismuth compounds are used for the treatment of gastrointestinal disorders and may also be useful for the treatment of other diseases. Bi(III) exhibits a highly variable coordination number (3-10) and often an irregular coordination geometry. To date, a large number of transition-metal complexes with dithiocarbamate have been synthesized and structurally characterized, including Ni(S_2CNC_4H_8O)_2、Cu(S_2CNC_4H_8)_2、Zn(S_2CNC_4H_8O)_2、Fe(S_2CNC_4H_8O)_2(DMF).
However, the chemistry of main-group metal complexes with dithiocarbamate has been scarcely studied, and a few reports have appeared on the synthesis and structures of the bismuth(Ⅲ) complexes with dithiocarbamate. Through its versatile coordination and connecting mode of dithiocarbamate and xanthate, we have synthesized some bismuth (III) complexes with dithiocarbamate and xanthate, and determined its structure by using X-ray single-crystal diffraction. Furthermore, their spectral properties and molecular structures have been studies carefully with elemental, IR and single crystal X-ray diffraction. According to the difference of their structures, the main contributions of the thesis are as follows:
1、Preparations a series of N, N-dialkyldithiocarbamate R_2NCS_2Na (R_2N= Me_2N, Et_2N, (CH_2)4N, (CH_2)5N, O(CH_2CH_2)_2N, C_6H_(12)N, Cy_2N, Bz_2N, MeN(CH_2CH_2)_2N, EtN(CH_2CH_2)_2N, BzN(CH_2CH_2)_2N) and O-alkylxanthate ROCS_2Na(RO= EtO, i-PrO, i-BuO)。
2、Syntheses eight new nitrate bismuth(III) compounds by reaction of bismuth nitrate with N,N-dialkyldithiocarbamate or 1,10-Phen or 2,2’-Bpy in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that geometry configuration of these bismuth(III) compounds are usually depicted as monomeric. The dithiocarbamate ligands all are linked to central tin atoms in an bidentate fashion. According to the Bi-S distances and reaction condition, we find that the greater spatial resistence from alkyl group is, the weaker the bismuth-sulfur coordination bond is, the harder reaction condition is. The sequence is N,N-dibenzyl> N -benzylpiperazinyl>piperidyl. Interestingly, these molecules are further linked to 1D or 2D supramolecular structures through intermolecular C-H···S and C-H···O interactions.
3、Syntheses five new chlorobismuth(III) compounds by reaction of bismuth chloride with N,N-dialkyldithiocarbamate or 1,10-Phen in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that in the chlorobismuth derivatives of N -benzylpiperazinyldithiocarbamate, the products are thirty-four-nuclear macrocycles and their structures don’t display apparent difference. Interestingly, these macrocyclic molecules are further linked to 1D or 2D supramolecular structures through intermolecular C-H···S interactions.
4、Syntheses four new bromicbismuth(III) compounds by reaction of bismuth bromide with N,N-dialkyldithiocarbamate in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that in the bromicbismuth(III) derivatives of N,N-dialkyldithiocarbamate, the products are dimmer、six-nuclear macrocycles、1D. And these molecules are further linked to form 1D or 2D supramolecular structures through intermolecular C-H···Br and C-H···S interactions.
5、Syntheses nine new iodobismuth(III) compounds by reaction of bismuth iodide with N,N-dialkyldithiocarbamate or 1,10-Phen or 4,4’-Bpy in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that in the iodobismuth(III) derivatives the products linked by iodide atoms are dimmer、1D. And these molecules are further linked to form 1D or 2D supramolecular structures through intermolecular C-H···I and C-H···S interactions.
6、Syntheses nine new halogenated bismuth(III) compounds by reaction of bismuth halogen with xanthate or 1,10-Phen in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that in the bismuth halogen with xanthate and 1,10-Phen, the products are further linked to 1D network through intermolecularπ···πand C-H···S interactions. Reaction of bismuth halogen with ?-BuOxanthate under solvothermal condition and obtained a coordination polymer, [Bi(S_2COC3H7)3]n. In this coordination polymer, the products are further linked to 1D network through intermolecular Bi···S interactions.
目前,铋的含硫配合物的合成及结构研究也已经有较多报道,但铋的氨荒酸及黄原酸衍生物也只有少量的研究报道。本文通过氨荒酸及黄原酸配体的丰富多样的配位和连接方式,通过实验合成了具有各种结构特性的铋的氨荒酸及黄原酸配合物的晶体,通过对产物的元素分析、红外光谱和X-射线单晶衍射等分析手段,确定生成产物的性质和结构,根据产物结构推测反应的过程和形成机理,并对其自组装反应和产物的超分子结构进行了较为系统的研究。主要工作如下:
1.制得了一系列N,N-二烃基氨荒酸盐R_2NCS_2Na(R_2N= Me_2N, Et_2N, (CH_2)4N, (CH_2)5N, O(CH_2CH_2)_2N, C_6H_(12)N, Cy_2N, Bz_2N, MeN(CH_2CH_2)_2N, EtN(CH_2CH_2)_2N, BzN(CH_2CH_2)_2N)和O-烃基黄原酸盐ROCS_2Na(RO= EtO, i-PrO, i-BuO)。
2.利用硝酸铋与N, N-二烃基氨荒酸盐以及中性配体反应,合成了八种新的硝酸铋类氨荒酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,此类铋化合物一般为单核结构;N, N-二烃基氨荒酸以及中性配体均以非均性二齿形式与中心铋原子配合。从配合物Bi-S键长以及反应的条件我们可以看出,空间位阻越大,配体就越难将反应物上的硝酸根取代,硫原子与铋原子之间的配位作用就越弱,对反应条件的要求也就越高。烃基的空间位阻顺序是:N,N-二苄基> N-苄基哌嗪>哌啶。有趣的是这些配合物进一步通过分子间的C-H···S和C-H···O等弱氢键作用形成了有趣的二维网状超分子结构。
3.利用氯化铋与N, N-二烃基氨荒酸盐以及中性配体反应,合成了五种新的氯化铋类氨荒酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,N-苄基哌嗪氨荒酸盐与氯化铋反应,经过自组装反应,得到了一个34元的环状结构的超分子配位聚合物。有趣的是这些配合物进一步通过分子间的C-H···S弱氢键作用形成了一维链状或二维网状的超分子结构。
4.利用溴化铋与N, N-二烃基氨荒酸盐反应,合成了四种新的溴化铋类氨荒酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,所有配合物均通过溴桥连接成二聚体、三核的六员环或者是一维链状结构。这些化合物进一步通过分子间的C-H···S和C-H···Br等氢键作用组装成一维链状或二维网状的超分子结构。
5.利用碘化铋与N, N-二烃基氨荒酸盐以及中性配体反应,合成了九种新的碘化铋类氨荒酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,部分配合物通过碘桥连接成二聚体或者是一维链状结构。这些化合物进一步通过分子间的C-H···S和C-H···I等氢键作用组装成一维链状或二维网状的超分子结构。
6.利用卤化铋与O-烃基黄原酸盐以及中性配体反应,合成了四种新的铋类黄原酸配合物。通过元素分析、红外光谱及X-射线单晶衍射法对其产物的性质与结构进行了系统研究。结果表明,有中性配体参与反应形成的配合物通过π-π堆积和分子间S···S等作用,形成作用较弱的超分子一维链状结构。没有中性配体参与反应形成的配合物通过硫桥形成一维链状结构。
Due to the nontoxic characters of bismuth and pebiological activities, bismuth(III) complexes have been extensively investigated. Bismuth compounds are used for the treatment of gastrointestinal disorders and may also be useful for the treatment of other diseases. Bi(III) exhibits a highly variable coordination number (3-10) and often an irregular coordination geometry. To date, a large number of transition-metal complexes with dithiocarbamate have been synthesized and structurally characterized, including Ni(S_2CNC_4H_8O)_2、Cu(S_2CNC_4H_8)_2、Zn(S_2CNC_4H_8O)_2、Fe(S_2CNC_4H_8O)_2(DMF).
However, the chemistry of main-group metal complexes with dithiocarbamate has been scarcely studied, and a few reports have appeared on the synthesis and structures of the bismuth(Ⅲ) complexes with dithiocarbamate. Through its versatile coordination and connecting mode of dithiocarbamate and xanthate, we have synthesized some bismuth (III) complexes with dithiocarbamate and xanthate, and determined its structure by using X-ray single-crystal diffraction. Furthermore, their spectral properties and molecular structures have been studies carefully with elemental, IR and single crystal X-ray diffraction. According to the difference of their structures, the main contributions of the thesis are as follows:
1、Preparations a series of N, N-dialkyldithiocarbamate R_2NCS_2Na (R_2N= Me_2N, Et_2N, (CH_2)4N, (CH_2)5N, O(CH_2CH_2)_2N, C_6H_(12)N, Cy_2N, Bz_2N, MeN(CH_2CH_2)_2N, EtN(CH_2CH_2)_2N, BzN(CH_2CH_2)_2N) and O-alkylxanthate ROCS_2Na(RO= EtO, i-PrO, i-BuO)。
2、Syntheses eight new nitrate bismuth(III) compounds by reaction of bismuth nitrate with N,N-dialkyldithiocarbamate or 1,10-Phen or 2,2’-Bpy in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that geometry configuration of these bismuth(III) compounds are usually depicted as monomeric. The dithiocarbamate ligands all are linked to central tin atoms in an bidentate fashion. According to the Bi-S distances and reaction condition, we find that the greater spatial resistence from alkyl group is, the weaker the bismuth-sulfur coordination bond is, the harder reaction condition is. The sequence is N,N-dibenzyl> N -benzylpiperazinyl>piperidyl. Interestingly, these molecules are further linked to 1D or 2D supramolecular structures through intermolecular C-H···S and C-H···O interactions.
3、Syntheses five new chlorobismuth(III) compounds by reaction of bismuth chloride with N,N-dialkyldithiocarbamate or 1,10-Phen in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that in the chlorobismuth derivatives of N -benzylpiperazinyldithiocarbamate, the products are thirty-four-nuclear macrocycles and their structures don’t display apparent difference. Interestingly, these macrocyclic molecules are further linked to 1D or 2D supramolecular structures through intermolecular C-H···S interactions.
4、Syntheses four new bromicbismuth(III) compounds by reaction of bismuth bromide with N,N-dialkyldithiocarbamate in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that in the bromicbismuth(III) derivatives of N,N-dialkyldithiocarbamate, the products are dimmer、six-nuclear macrocycles、1D. And these molecules are further linked to form 1D or 2D supramolecular structures through intermolecular C-H···Br and C-H···S interactions.
5、Syntheses nine new iodobismuth(III) compounds by reaction of bismuth iodide with N,N-dialkyldithiocarbamate or 1,10-Phen or 4,4’-Bpy in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that in the iodobismuth(III) derivatives the products linked by iodide atoms are dimmer、1D. And these molecules are further linked to form 1D or 2D supramolecular structures through intermolecular C-H···I and C-H···S interactions.
6、Syntheses nine new halogenated bismuth(III) compounds by reaction of bismuth halogen with xanthate or 1,10-Phen in different stoichiometry. Their spectral properties and molecular structures have been studies carefully with elemental, IR analyses and single crystal X-ray diffraction. The results show that in the bismuth halogen with xanthate and 1,10-Phen, the products are further linked to 1D network through intermolecularπ···πand C-H···S interactions. Reaction of bismuth halogen with ?-BuOxanthate under solvothermal condition and obtained a coordination polymer, [Bi(S_2COC3H7)3]n. In this coordination polymer, the products are further linked to 1D network through intermolecular Bi···S interactions.
引文
[1] 孟庆金, 戴安邦编. 配位化学的创始与现代化, 北京:高等教育出版社. 1998.
[2] Sun, H.; Sadler, P. J. Top Biol Inorg Chem, 1999, 2: 159.
[3] Slikkerveer, A.; de Wolff, F. A. Med Toxical Adverse Drug Exp., 1989, 4: 303.
[4] Menge, H.; Gregor, M.; Brosius, B. Eur J Gastroenterol Hepatol., 1994, 4(S2): 41.
[5] Clitherow, J. W. United Kingdom Patent GB2220937A, 1990.
[6] 彭寿清. 金属世界, 1997, 23.
[7] Atwood, D. A.; Cowley, A. H.; Hernandez, R. D.; Jones, R. A. Inorg. Chem., 1993, 32: 2972.
[8] Klafitke, T.; Gowik, P. Z. Naturforsch, 1987, B42: 940.
[9] Kepi, M. P.; Klapbtke, T. Inorg. Chim. Acta, 1988, 152: 49.
[10] Graham, D. Y. Helicobacter Pylori Basic Mechanisms to Clinical Cure, Kcluwer Academic Pulishers, Boston, MA. 1994, 531.
[11] Jiang, M. X. Chief-Edr. Pharmacology, 3rd Edn. Beijing: People health press. 1992, 262.
[12]汪立果. 稀有金属, 1991, 15(1): 44.
[13] Lee, S. S. T.; Scott, J. G. International Pest Control, 1985, 27(6): 144.
[14] Sheng, T. L.; Wu, X. T.; Lin, P.; Zhang, W. J.; Wang, Q. M.; Chen L. Polyhedron, 1999, 18: 1049.
[15] Iztok, T.; Ljubo, Golic.; Peter, B.; Marija, G. J. J. Inorg. Biochem., 1998, 71: 53.
[16] Peach, M. E. J. Inorg. Nucl. Chem., 1979, 41: 1392.
[17] Muller, M.; Clark, R. J. H.; Nyholm, R. S. Transition Met. Chem., 1978, 3: 369.
[18] Gilman, H.; Yale, H. L. J. Am. Chem. Soc., 1951, 73: 2880.
[19] Wieber, M.; Baudis, U. Z. Anorg. Allg. Chem., 1976, 423: 47.
[20] Jansen, A. F.; Vaidya, O. C.; Willis, C. J. J. Inorg. Nucl. Chem., 1981, 43: 1469.
[21] Hergett, S. C.; Peach, M. E. J. Fluorine Chem., 1988, 38: 367.
[22] Sundvall, B. Inorg. Chem., 1983, 22: 1906.
[23] Lawlor, F. J.; Norman, N. C. Polyhedron, 1995, 14: 311.
[24] Battaglia, L. P.; Corradi, A. B. J. Chem. Soc. Dalton Trans., 1983, 2425.
[25] Battaglia, L. P.; Corradi, A. B.; Pelizzi, G.; Vidoni, Tani M. E. J. Chem. Soc. Dalton Trans., 1977, 1141.
[26] Cremer, D.; Pople, J. A. J. Am. Chem. Soc., 1975, 97: 1354.
[27] Healy, P. C.; White, A. H. J. Am. Chem. Soc., 1972, 1163.
[28] Newman, P. W. G.; Raston, C. L.; White, A. H. J. Am. Chem. Soc., 1973, 1332.
[29] Golub, A. M.; Kohler, H.; Skopenko, V. V. Chemistry of Pseudohalides, Elsevier, Amsterdam. 1986.
[30] Crispini, A..; Errington, R. J.; Fisher, G. A.; Funke, F. J.; Norman, N. C.; Orpen, A. G.; Stratford, S. E.; Struve, O. J. Chem. Soc. Dalton Trans., 1994, 1327.
[31] Carmalt, C. J.; Cowley, A. H.; Decken, A.; Lawson, Y. G.; Norman, N. C. Organometallics, 1996, 15: 887.
[32] Carmalt, C. J.; Cowley, A. H.; Decken, A.; Norman, N. C. J. Organomet. Chem., 1995, 496: 59.
[33] Massiani, M. C.; Papiernik, R.; Hubert-Pfalzgraf, L. G.; Daran, J. C. J. Chem. Soc. Dalton Trans., 1990, 301.
[34] Rogers, R. D.; Bond, A. H.; Aguinaga, S.; Reyers, A. J. Am. Chem. Soc., 1992, 114: 2967.
[35] Jolas, J. L.; Hoppe, S.; Whitmire, K. H. Inorg. Chem., 1997, 36: 3335.
[36] Raston, C. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1976, 791.
[37] Uson, R.; Laguna, A.; Laguna, M.; Jones, P. G.; Sheldrick, G. M. J. Chem. Soc. Dalton Trans., 1981, 366.
[38] Raston, C. L.; Rowbottom, G. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1981, 1389.
[39] Ng, S. W.; Kumar, V. G. J. Organomet. Chem., 1991, 403: 111.
[40] Massiani, M. C.; Papiernik, R.; Liliane, G. Polyhedron, 1991, 10: 437.
[41] Jones, C. M.; Michanel, M. D.; Hachman, R. E. Inorg. Chem., 1993, 32: 5126.
[42] Breeze, S. R.; Liqin, C.; Sunning, W. J. Chem. Soc. Dalton Trans., 1994, 2545.
[43] Boyle, T. J.; Pedrotty, D. M.; Scott B. Polyhedron, 1998, 17: 1959.
[44] Battaglin, L. P.; Corradi, A. B. J. Chem. Soc. Dalton Trans., 1986, 15: 137.
[45] Battaglin, L. P.; Corradi, A. B.; Nardelli, M.; Tani, M. E. J. Chem. Soc. Dalton Trans., 1978, 583.
[46] Stephan, W.; Dieter, L.; Konrad, S. Inorg. Chem.,1993, 32: 3948.
[47] Bertazzi, N.; Alonzo, G.; Battaglia, L. P.; Corradi, A. B.; Pelosi, G. J. Chem. Soc. Dalton Trans., 1990, 2403.
[48] Crown, A. J.; Smith, P. J.; Atassi, G. Chem. Biol. Interact., 1980, 32: 171.
[49] Cvengrosova, Z.; Hronec, M.; Rattay, V. Commun., 1986, 9(1-2): 55.
[50] 张海军, 薛王兰. 云南冶金, 1998, 27(1): 28.
[51]陈卫国, 任欣, 朱锡涛. 环境化学, 1997, 16(3): 220.
[52] Xie, J.; Funakoshi, T.; Shimada, H.; Kojima, S. Res. Commun. Mol. Pathol. Pharmacol., 1994, 86(2): 245.
[53] Gringeri, A.; Keng, P.C.; Borch, R. F. Cancer Res., 1988, 48: 5708.
[54] Cale, G. R.; Atkins, L. M.; Walker, E. M.; Smith, A. B.; Jones M. M. Clin. Lab. Sci., 1984, 14: 137.
[55] Metcalf, R. L.; Fukuto, T. R.; Fredeickson, M. J. Agro. Food Chem., 1965, 13: 473.
[56] Thron, G. D.; Ludwig, R. A. The dithiocarbamates and related compounds, Elsevier. Amsterdam. 1962.
[57] Rickkola, M. L.; Pakkanen, T.; Niinisto, L. Acta Chemica Scand, 1983, A37: 807.
[58] Jeng, Y. R. Lubrication Engineering, 2002, 58(2): 9.
[59] Otsu, T.; Kuriyama, A. Polymer Bulletin, 1984, 11(2): 135.
[60] Obara, N. USP4461583, Jul,7,1984.
[61]陈卫国, 任欣, 朱锡涛. 环境化学, 1997,16(3): 220.
[62] Raston, C. L.; Rowbottom, G. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1981, 1366.
[63] Allen, F. H.; Kennard, O.; Galloy, J. J.; Johnson, O.; Waston, D. G. Chem. Des. Autom. News, 1993, 8: 31.
[64] Rardaji, M.; Connelly, N. G.; Gimeno, M. C.; Jimenez, J.; Jones, P. G.; Laguna, A.; Lagnna, M. J. Chem. Soc. Dalton Trans., 1994, 1163.
[65] Sisido, K. J. Am. Chem. Soc., 1961, 83: 588.
[66] Russeva, E.; Budevsky, O. Talanta, 1973, 20: 1329.
[67] Coutts, R. S. P. Aust. J. Chem., 1974, 27: 2483.
[68] Nakmoto, K. J. Chem. Phys., 1963, 39: 423.
[69]黄宪, 陈振初编著. 有机合成化学[M], 北京:化学工业出版社, 1988, 632.
[70] Marion, W.; Harmon. USP2372895, Apr. 3, 1945.
[71] 王雪梅. 辽宁化工., 1999, 28(3): 135.
[72] 王瑛, 张建强, 姜涛等. 有机化学, 2003, 23: 690.
[73] Pan, S., Wang, Y. Chin. J. Chem., 2001, 19: 856.
[74] Jian, F. F.; Xue, T.; Jiao, K.; Zhang, S. S. Chin. J. Chem.,. 2003, 21: 50.
[75] Deng, Y. H.; Wen, T. B.; Liu, Q. T.; Zhu, H. P.; Chen, C. N. Inorg. Chim. Acta, 1999, 293: 95.
[76] Guo, S. L.; Yin, Y. Q. J. Sichuan Univ., 1999, 36: 562.
[77] Fisher, G. A.; Norman, N. C. Inorg. Chem., 1994, 41: 233.
[78] Yin, H. D.; Wang, C. H.; Xing, Q. J. Chin. J. Inorg. Chem., 2003, 19: 955.
[79] Buckingham, D. A.; Clark, C. R.; Nangia, A. Aust. J. Chem. 1990, 43: 301.
[80] Foy, R. M.; Kepert, D. L.; Raston, C. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1980, 440.
[81] Battaglia, L. P.; Corradi, A. B. J. Chem. Soc. Dalton Trans., 1981, 23.
[82] Farrugia, L. J.; Lawlor, F. J.; Norman, N. C. J. Chem. Soc. Dalton Trans., 1995, 1163.
[83] Boyle, T. J.; Alam, T. M.; Mechenbeir, E. R.; Scott, B.; Ziller, J. W. Inorg. Chem., 1997, 36: 3293.
[84] 曾明华, 梁宏, 胡瑞祥等. 应用化学, 2001, 18: 839.
[85] 项光其, 林秀雅, 胡茂林. 温州师范学院学报, 2003, 24: 21.
[86] Yin, H. D.; Zhang, R. F.; Ma, C. L. ACH-Models Chem., 1999, 136: 333.
[87] Raston, C. L.; Rowbottom, G. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1981, 1379.
[88] Reperuma, O.; Feltham, R. D. Inorg. Chem., 1975, 14: 12.
[89] 中本一维著, 黄懿和, 王庆仁译. 无机和配位化合物的红外光谱和拉曼光谱, 北京:化学工业出版社, 1986, 356.
[90] 李润涛,葛泽梅,高等学校化学学报,1999, 20: 1897.
[91] 尹汉东,张茹芬,马春林等,聊城师范学院学报,1999, 12: 38.
[92] 韩巧凤, 番寿龙, 杨绪杰, 汪信, 江苏化工, 2002, 30(3): 33.
[93] 尹汉东,王传华,马春林,有机化学,2004, 24: 34.
[94] Yao, K. M.; Li, D. C.; Shen, L. F.; Yuan, H. Z. Acta Chim. Sinica, 1993, 51: 897.
[95] Bonozi, F. J. Organomet. Chem. 1967, 9: 395.
[96] Metz, J.; Schneider, O.; Hanack, M. Spectrochim. Acta. 1982, 38A: 1265.
[97] Li, B. L.; Xu, Y.; Liu, Q.; Chen, T. J.; Wang, Q. H.; Xu, Z.; J. Mol. Struc. 2001, 597: 21..
[98] Beadle, P. J.; Goldstein, M.; Goodgame, L. M. D.; Grzeskowiak, R. Inorg. Chem. 1969, 8: 1490.
[99] Raston, C. L.; White, A. H.; Winter, G. Aust. J. Chem. 1978, 31: 2207.
[100] Curtis, N. F.; Curtis, Y. M. Inorg. Chem., 1983, 4: 804.
[101] Boyle, T. J.; Schwartz, R. W.; Doedens, R. J.; Ziller, J. W. Inorg. Chem., 1995, 34: 1110.
[102] Raston, C. L.; Rowbottom, G. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1981, 1352.
[103] Crispini, A..; Errington, R. J.; Fisher, G. A.; Funke, F. J.; Norman, N. C.; Orpen, A. G.; Stratford, S. E.; Struve, O. J. Chem. Soc. Dalton Trans., 1994, 1327.
[104] Battaglia, L. P.; Corradi, A. B.; Pelosi, G.; Tarascini, P. J. Chem. Soc. Dalton Trans., 1989, 671.
[105] 尹汉东, 王传华, 许福泉. 无机化学学报, 2004, 20: 345.
[106] 尹汉东, 王传华, 许福泉. 无机化学学报, 2003, 19: 955.
[107] 尹汉东, 王传华, 许福泉. 结构化学,2004, 23: 1201.
[108] 尹汉东, 王传华, 王大奇. 有机化学, 2004, 24: 658. [109 ] Atwood, D. A.; Cowley, A. H.; Hernandez, R. D. et al. Inorg. Chem., 1993, 32: 2972.
[110] Breeze, S. R.; Chen, L. Q.; Wang, S. N. J. Chem. Soc., Dalton Trans., 1994, 2545.
[111] Massiani, M. C.; Papiernik, R.; Hubert-pfalzgraf L G. Polyhedron, 1991, 10: 437.
[112] Yin, H. D.; Wang, C. H.; Xing, Q. J. Chem. Res. Chinese U. 2004, 20: 565.
[113] Battaglia, L. P.; Corradi, A. B.; Pelizzi, G.; Vidoni, Tani M. E. J. Chem. Soc. Dalton Trans., 1977, 1141.
[114] George T. A.; Jones K.; Lapert M. F. J. Chem. Soc., 1965, 2157.
[115] Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112: 5525.
[116] Janiak, C. J. Chem. Soc., Dalton Trans. 2000, 3885.
[117] Onoue, K.; Osawa, Y.; etc. Bull. Chem. Soc. Jpn. 1997, 70: 1961.
[118] Ortholand, J. Y.; Slawin, A. M. Z.; Spencer, N.; etc. Angew. Chem., Int. Ed. Engl. 1989, 28: 1394.
[2] Sun, H.; Sadler, P. J. Top Biol Inorg Chem, 1999, 2: 159.
[3] Slikkerveer, A.; de Wolff, F. A. Med Toxical Adverse Drug Exp., 1989, 4: 303.
[4] Menge, H.; Gregor, M.; Brosius, B. Eur J Gastroenterol Hepatol., 1994, 4(S2): 41.
[5] Clitherow, J. W. United Kingdom Patent GB2220937A, 1990.
[6] 彭寿清. 金属世界, 1997, 23.
[7] Atwood, D. A.; Cowley, A. H.; Hernandez, R. D.; Jones, R. A. Inorg. Chem., 1993, 32: 2972.
[8] Klafitke, T.; Gowik, P. Z. Naturforsch, 1987, B42: 940.
[9] Kepi, M. P.; Klapbtke, T. Inorg. Chim. Acta, 1988, 152: 49.
[10] Graham, D. Y. Helicobacter Pylori Basic Mechanisms to Clinical Cure, Kcluwer Academic Pulishers, Boston, MA. 1994, 531.
[11] Jiang, M. X. Chief-Edr. Pharmacology, 3rd Edn. Beijing: People health press. 1992, 262.
[12]汪立果. 稀有金属, 1991, 15(1): 44.
[13] Lee, S. S. T.; Scott, J. G. International Pest Control, 1985, 27(6): 144.
[14] Sheng, T. L.; Wu, X. T.; Lin, P.; Zhang, W. J.; Wang, Q. M.; Chen L. Polyhedron, 1999, 18: 1049.
[15] Iztok, T.; Ljubo, Golic.; Peter, B.; Marija, G. J. J. Inorg. Biochem., 1998, 71: 53.
[16] Peach, M. E. J. Inorg. Nucl. Chem., 1979, 41: 1392.
[17] Muller, M.; Clark, R. J. H.; Nyholm, R. S. Transition Met. Chem., 1978, 3: 369.
[18] Gilman, H.; Yale, H. L. J. Am. Chem. Soc., 1951, 73: 2880.
[19] Wieber, M.; Baudis, U. Z. Anorg. Allg. Chem., 1976, 423: 47.
[20] Jansen, A. F.; Vaidya, O. C.; Willis, C. J. J. Inorg. Nucl. Chem., 1981, 43: 1469.
[21] Hergett, S. C.; Peach, M. E. J. Fluorine Chem., 1988, 38: 367.
[22] Sundvall, B. Inorg. Chem., 1983, 22: 1906.
[23] Lawlor, F. J.; Norman, N. C. Polyhedron, 1995, 14: 311.
[24] Battaglia, L. P.; Corradi, A. B. J. Chem. Soc. Dalton Trans., 1983, 2425.
[25] Battaglia, L. P.; Corradi, A. B.; Pelizzi, G.; Vidoni, Tani M. E. J. Chem. Soc. Dalton Trans., 1977, 1141.
[26] Cremer, D.; Pople, J. A. J. Am. Chem. Soc., 1975, 97: 1354.
[27] Healy, P. C.; White, A. H. J. Am. Chem. Soc., 1972, 1163.
[28] Newman, P. W. G.; Raston, C. L.; White, A. H. J. Am. Chem. Soc., 1973, 1332.
[29] Golub, A. M.; Kohler, H.; Skopenko, V. V. Chemistry of Pseudohalides, Elsevier, Amsterdam. 1986.
[30] Crispini, A..; Errington, R. J.; Fisher, G. A.; Funke, F. J.; Norman, N. C.; Orpen, A. G.; Stratford, S. E.; Struve, O. J. Chem. Soc. Dalton Trans., 1994, 1327.
[31] Carmalt, C. J.; Cowley, A. H.; Decken, A.; Lawson, Y. G.; Norman, N. C. Organometallics, 1996, 15: 887.
[32] Carmalt, C. J.; Cowley, A. H.; Decken, A.; Norman, N. C. J. Organomet. Chem., 1995, 496: 59.
[33] Massiani, M. C.; Papiernik, R.; Hubert-Pfalzgraf, L. G.; Daran, J. C. J. Chem. Soc. Dalton Trans., 1990, 301.
[34] Rogers, R. D.; Bond, A. H.; Aguinaga, S.; Reyers, A. J. Am. Chem. Soc., 1992, 114: 2967.
[35] Jolas, J. L.; Hoppe, S.; Whitmire, K. H. Inorg. Chem., 1997, 36: 3335.
[36] Raston, C. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1976, 791.
[37] Uson, R.; Laguna, A.; Laguna, M.; Jones, P. G.; Sheldrick, G. M. J. Chem. Soc. Dalton Trans., 1981, 366.
[38] Raston, C. L.; Rowbottom, G. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1981, 1389.
[39] Ng, S. W.; Kumar, V. G. J. Organomet. Chem., 1991, 403: 111.
[40] Massiani, M. C.; Papiernik, R.; Liliane, G. Polyhedron, 1991, 10: 437.
[41] Jones, C. M.; Michanel, M. D.; Hachman, R. E. Inorg. Chem., 1993, 32: 5126.
[42] Breeze, S. R.; Liqin, C.; Sunning, W. J. Chem. Soc. Dalton Trans., 1994, 2545.
[43] Boyle, T. J.; Pedrotty, D. M.; Scott B. Polyhedron, 1998, 17: 1959.
[44] Battaglin, L. P.; Corradi, A. B. J. Chem. Soc. Dalton Trans., 1986, 15: 137.
[45] Battaglin, L. P.; Corradi, A. B.; Nardelli, M.; Tani, M. E. J. Chem. Soc. Dalton Trans., 1978, 583.
[46] Stephan, W.; Dieter, L.; Konrad, S. Inorg. Chem.,1993, 32: 3948.
[47] Bertazzi, N.; Alonzo, G.; Battaglia, L. P.; Corradi, A. B.; Pelosi, G. J. Chem. Soc. Dalton Trans., 1990, 2403.
[48] Crown, A. J.; Smith, P. J.; Atassi, G. Chem. Biol. Interact., 1980, 32: 171.
[49] Cvengrosova, Z.; Hronec, M.; Rattay, V. Commun., 1986, 9(1-2): 55.
[50] 张海军, 薛王兰. 云南冶金, 1998, 27(1): 28.
[51]陈卫国, 任欣, 朱锡涛. 环境化学, 1997, 16(3): 220.
[52] Xie, J.; Funakoshi, T.; Shimada, H.; Kojima, S. Res. Commun. Mol. Pathol. Pharmacol., 1994, 86(2): 245.
[53] Gringeri, A.; Keng, P.C.; Borch, R. F. Cancer Res., 1988, 48: 5708.
[54] Cale, G. R.; Atkins, L. M.; Walker, E. M.; Smith, A. B.; Jones M. M. Clin. Lab. Sci., 1984, 14: 137.
[55] Metcalf, R. L.; Fukuto, T. R.; Fredeickson, M. J. Agro. Food Chem., 1965, 13: 473.
[56] Thron, G. D.; Ludwig, R. A. The dithiocarbamates and related compounds, Elsevier. Amsterdam. 1962.
[57] Rickkola, M. L.; Pakkanen, T.; Niinisto, L. Acta Chemica Scand, 1983, A37: 807.
[58] Jeng, Y. R. Lubrication Engineering, 2002, 58(2): 9.
[59] Otsu, T.; Kuriyama, A. Polymer Bulletin, 1984, 11(2): 135.
[60] Obara, N. USP4461583, Jul,7,1984.
[61]陈卫国, 任欣, 朱锡涛. 环境化学, 1997,16(3): 220.
[62] Raston, C. L.; Rowbottom, G. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1981, 1366.
[63] Allen, F. H.; Kennard, O.; Galloy, J. J.; Johnson, O.; Waston, D. G. Chem. Des. Autom. News, 1993, 8: 31.
[64] Rardaji, M.; Connelly, N. G.; Gimeno, M. C.; Jimenez, J.; Jones, P. G.; Laguna, A.; Lagnna, M. J. Chem. Soc. Dalton Trans., 1994, 1163.
[65] Sisido, K. J. Am. Chem. Soc., 1961, 83: 588.
[66] Russeva, E.; Budevsky, O. Talanta, 1973, 20: 1329.
[67] Coutts, R. S. P. Aust. J. Chem., 1974, 27: 2483.
[68] Nakmoto, K. J. Chem. Phys., 1963, 39: 423.
[69]黄宪, 陈振初编著. 有机合成化学[M], 北京:化学工业出版社, 1988, 632.
[70] Marion, W.; Harmon. USP2372895, Apr. 3, 1945.
[71] 王雪梅. 辽宁化工., 1999, 28(3): 135.
[72] 王瑛, 张建强, 姜涛等. 有机化学, 2003, 23: 690.
[73] Pan, S., Wang, Y. Chin. J. Chem., 2001, 19: 856.
[74] Jian, F. F.; Xue, T.; Jiao, K.; Zhang, S. S. Chin. J. Chem.,. 2003, 21: 50.
[75] Deng, Y. H.; Wen, T. B.; Liu, Q. T.; Zhu, H. P.; Chen, C. N. Inorg. Chim. Acta, 1999, 293: 95.
[76] Guo, S. L.; Yin, Y. Q. J. Sichuan Univ., 1999, 36: 562.
[77] Fisher, G. A.; Norman, N. C. Inorg. Chem., 1994, 41: 233.
[78] Yin, H. D.; Wang, C. H.; Xing, Q. J. Chin. J. Inorg. Chem., 2003, 19: 955.
[79] Buckingham, D. A.; Clark, C. R.; Nangia, A. Aust. J. Chem. 1990, 43: 301.
[80] Foy, R. M.; Kepert, D. L.; Raston, C. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1980, 440.
[81] Battaglia, L. P.; Corradi, A. B. J. Chem. Soc. Dalton Trans., 1981, 23.
[82] Farrugia, L. J.; Lawlor, F. J.; Norman, N. C. J. Chem. Soc. Dalton Trans., 1995, 1163.
[83] Boyle, T. J.; Alam, T. M.; Mechenbeir, E. R.; Scott, B.; Ziller, J. W. Inorg. Chem., 1997, 36: 3293.
[84] 曾明华, 梁宏, 胡瑞祥等. 应用化学, 2001, 18: 839.
[85] 项光其, 林秀雅, 胡茂林. 温州师范学院学报, 2003, 24: 21.
[86] Yin, H. D.; Zhang, R. F.; Ma, C. L. ACH-Models Chem., 1999, 136: 333.
[87] Raston, C. L.; Rowbottom, G. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1981, 1379.
[88] Reperuma, O.; Feltham, R. D. Inorg. Chem., 1975, 14: 12.
[89] 中本一维著, 黄懿和, 王庆仁译. 无机和配位化合物的红外光谱和拉曼光谱, 北京:化学工业出版社, 1986, 356.
[90] 李润涛,葛泽梅,高等学校化学学报,1999, 20: 1897.
[91] 尹汉东,张茹芬,马春林等,聊城师范学院学报,1999, 12: 38.
[92] 韩巧凤, 番寿龙, 杨绪杰, 汪信, 江苏化工, 2002, 30(3): 33.
[93] 尹汉东,王传华,马春林,有机化学,2004, 24: 34.
[94] Yao, K. M.; Li, D. C.; Shen, L. F.; Yuan, H. Z. Acta Chim. Sinica, 1993, 51: 897.
[95] Bonozi, F. J. Organomet. Chem. 1967, 9: 395.
[96] Metz, J.; Schneider, O.; Hanack, M. Spectrochim. Acta. 1982, 38A: 1265.
[97] Li, B. L.; Xu, Y.; Liu, Q.; Chen, T. J.; Wang, Q. H.; Xu, Z.; J. Mol. Struc. 2001, 597: 21..
[98] Beadle, P. J.; Goldstein, M.; Goodgame, L. M. D.; Grzeskowiak, R. Inorg. Chem. 1969, 8: 1490.
[99] Raston, C. L.; White, A. H.; Winter, G. Aust. J. Chem. 1978, 31: 2207.
[100] Curtis, N. F.; Curtis, Y. M. Inorg. Chem., 1983, 4: 804.
[101] Boyle, T. J.; Schwartz, R. W.; Doedens, R. J.; Ziller, J. W. Inorg. Chem., 1995, 34: 1110.
[102] Raston, C. L.; Rowbottom, G. L.; White, A. H. J. Chem. Soc. Dalton Trans., 1981, 1352.
[103] Crispini, A..; Errington, R. J.; Fisher, G. A.; Funke, F. J.; Norman, N. C.; Orpen, A. G.; Stratford, S. E.; Struve, O. J. Chem. Soc. Dalton Trans., 1994, 1327.
[104] Battaglia, L. P.; Corradi, A. B.; Pelosi, G.; Tarascini, P. J. Chem. Soc. Dalton Trans., 1989, 671.
[105] 尹汉东, 王传华, 许福泉. 无机化学学报, 2004, 20: 345.
[106] 尹汉东, 王传华, 许福泉. 无机化学学报, 2003, 19: 955.
[107] 尹汉东, 王传华, 许福泉. 结构化学,2004, 23: 1201.
[108] 尹汉东, 王传华, 王大奇. 有机化学, 2004, 24: 658. [109 ] Atwood, D. A.; Cowley, A. H.; Hernandez, R. D. et al. Inorg. Chem., 1993, 32: 2972.
[110] Breeze, S. R.; Chen, L. Q.; Wang, S. N. J. Chem. Soc., Dalton Trans., 1994, 2545.
[111] Massiani, M. C.; Papiernik, R.; Hubert-pfalzgraf L G. Polyhedron, 1991, 10: 437.
[112] Yin, H. D.; Wang, C. H.; Xing, Q. J. Chem. Res. Chinese U. 2004, 20: 565.
[113] Battaglia, L. P.; Corradi, A. B.; Pelizzi, G.; Vidoni, Tani M. E. J. Chem. Soc. Dalton Trans., 1977, 1141.
[114] George T. A.; Jones K.; Lapert M. F. J. Chem. Soc., 1965, 2157.
[115] Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112: 5525.
[116] Janiak, C. J. Chem. Soc., Dalton Trans. 2000, 3885.
[117] Onoue, K.; Osawa, Y.; etc. Bull. Chem. Soc. Jpn. 1997, 70: 1961.
[118] Ortholand, J. Y.; Slawin, A. M. Z.; Spencer, N.; etc. Angew. Chem., Int. Ed. Engl. 1989, 28: 1394.