磺酰胺及其席夫碱过渡金属配合物的合成，表征和晶体结构
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摘要
本文以磺酰胺及其席夫碱为研究对象,选用乙二胺、丙二胺、邻苯二胺、二乙三胺以及联苯胺为原料,得到了五种磺酰胺及八种磺酰胺席夫碱配体。采用常规溶液法、微波以及电解反应的方法,合成了20种过渡金属的化合物,其中得到了18个化合物的单晶。用元素分析、X-射线单晶衍射、XRD、IR、UV-Vis、TG对化合物进行了表征,同时也进行了部分量子化学计算。
在第2和第3章中,以乙二胺为基础,合成了N-tosyl-乙二胺(Tsen),使其与水杨醛、5-溴水杨醛、2-羟基-1-萘醛以及吡啶甲醛反应,得到了4种磺酰胺Schiff碱配体,并以此为基础合成了它们的过渡金属配合物,得到了11个配合物的单晶,分别为[Cu(Tsen)_2](1)、[Cu(salTsen)(H_2O)](2)、[Cu(salTsen)_2](3)、[Ni(salTsen)_2](4)、[Zn(salTsen)_2]·H_2O(5)、[Cu(sal)(phen)]ClO_4(6)、[Cu(5-Brsal- Tsen)_2](7)、[Cu(5-BrsalTsen)(H_2O)](8)、[Cu(napnTsen)_2](9)、[Cu(naphTsen)(H_2O)]_2(10)和[Mn(pyTsen)_2Cl_2]·1.5H_2O(11)。
在第4章中,以1,2-丙二胺为基础,得到了一个Schiff碱配合物的单晶,[Cu(salTspn)(H_2O)](12)。以邻苯二胺为基础,得到了三个Schiff碱及其配合物,其中得到了一个配合物的单晶[Cu(salTsophan)(H_2O)](13)。
在第5章中,以二乙三胺为基础,得到了双磺酰化二乙三胺,与不同金属铜盐反应,得到了两个化合物的单晶,分别为[Cu_2(bisTsdeta)_2(H_2O)_2](17)和[Cu(mal)_2(bisTsdeta)_2·H_2O](18)。而反应条件改变时,还得到了磺酰基断裂的Schiff碱配合物[Cu(saldeta)(H_2O)]Cl(19)。以刚性的联苯胺为基础,得到了超分子化合物bisTsBZD·2DMF(20)。
对于磺酰胺席夫碱配体的配位模式来说,有负一价双齿HL·(3、4、5、7、9),负二价三齿L~(2-)(2、8、12、13)和负二价四齿μ_2桥联(10)三种。
对于配合物的结构来说,有磺酰基氧桥联的双核结构(10、17),酰胺或其席夫碱配位的单核结构(1、2、3、4、5、7、8、9、11、12、13),酰胺未配位的超分子结构(18、20)以及磺酰基断裂的单核配合物(6、16、19)。
从化合物的堆积模式来说,配合物2、8和12的配体具有相似的结构,其结构中都为螯合环与芳环间先以双重π…π作用形成双聚体,双聚体间以弱相互作用(2π…π和C—H…O,8π…π和O—H…O,12C—H…π和O—H…O)连接成二维(2、8)和三维结构(12):配合物3、7和9的配体中的醛不同,其分子间分别为π…π连成的一维链(3、7)和C—H…π形成的二维结构(9);配合物3、4、5的配体相同而金属离子不同,但分别以弱作用力(3π…π,4C—H…π,N—H…O和C—H…O,5C—H…π和N—H…O)堆积成一维(3)和三维结构(4、5);配合物10和13的配体相对于配合物2、8和12,刚性增强,则分别为弱作用力(10O—H…O、C—H…O和C—H…π,13π…π和Cu…O)形成的三维(10)和一维(13)结构。
磺酰胺的配合物1和17,均由弱作用力(1N—H…O和C—H…π:17C—H…π和C—H…O)连接成二维结构。
酰胺未配位的超分子化合物18和20,则分别为N—H…O连接成的二维结构与C—H…O连接成的三维结构。
磺酰基断裂残片的配合物6、16和19,分别为π…π形成的一维链(6、16)和N—H…Cl与O—H…O形成的二维结构(19)。
而且,化合物5和19中正是因为这些弱作用力的存在,形成了平面上的(4,4)拓扑结构。
In this paper,ethylenediamine,1,2-propanediamine,1,2-diaminobenzene, diethylenetriamine and benzidine were used as original materials based on sulfonamide and its Schiff base.5 sulfonamide and 8 sulfonamide Schiff base were obtained.20 compounds were prepared and 18 obtained as single crystals by general solution,microwave and electrochemical synthesis method.The obtained compounds were characterized by elemental analysis,X-ray single crystal diffraction,X-ray powder diffraction,IR,UV-Vis and TG-DSC.Moreover,some compounds were discussed by quantum chemistry results.
In chapter 2 and 3,N-tosyl-ethylenediamine(Tsen)were prepared and reacted with salicylaldehyde,5-Br-salicylaldehyde,2-hydroxy-1-naphthaldehyde and 2-pyridinealdehyde.4 sulfonamide Schiff base ligands were obtained and reacted with transitional metals.11 complexes as crystals were prepared,that is,[Cu(Tsen)_2](1), [Cu(salTsen)(H_2O)](2)、[Cu(salTsen)_2](3)、[Ni(salTsen)_2](4)、[Zn(salTsen)_2]·H_2O (5)、[Cu(sal)(phen)]ClO_4(6)、[Cu(5-BrsalTsen)_2](7)、[Cu(5-BrsalTsen)(H_2O)](8)、[Cu(napnTsen)_2](9)、[Cu(naphTsen)(H_2O)]_2(10)和[Mn(pyTsen)_2Cl_2]·1.5H_2O(11)。
In chapter 4,N-tosyl-propanediamine(Tspn)were prepared based on 1,2-propanediamine.And the corresponding Schiff base complex is obtained with the composition of[Cu(salTspn)(H_2O)](12).Also three Schiff base complexes based on N-tosyl-diaminebenzene(Tsophan)were prepared and one was obtained as single crystal with the composition of[Cu(salTsophan)(H_2O)](13).
In chapter 5,N,N"-tosyl-diethylenetriamine(BisTsdeta)were prepared based diethylenetriamine.Different compounds were obtained when BisTsdeta reacted with different metal salts,which are binuclear complex[Cu_2(bisTsdeta)_2(H_2O)_2](17)and supermolecule[Cu(mal)_2(bisTsdeta)_2·H_2O](18).Also complex[Cu(saldeta)(H_2O)]Cl (19)was obtained when the reaction condition changed.N,N'-Bistosylbenzidine (BistTsBZD)was obtained based on rigid benzidine,and the supermolecule BisTsBZD·2DMF(20)was obtained as single crystal.
There are three kinds of coordination mode of sulfonamide Schiff base,which are anionic bidentate HL~-(3,4,5,7,9),dianionic tridentate(2,8,12,13)and dianionicμ_2-bridged tetradentate(10).
For the structure of the compounds,there are binuclear structure bridged by the oxygen atom of tosyl group(10,17),mononuclear structure coordinated by sulfonamide or its Schiff base(1,2,3,4,5,7,8,9,11,12,13),supermolecule without the coordination of sulfonamide(18,20)and the monoclear complexes with the residue group in which the sulfonamide breaking in the iigand.
The supermolecule interactions are various in the crystal of the compounds.For complexes 2,8 and 12 having similar ligands,dimers are formed by the doubleπ…πinteractions between chelated ring and benzene ring of two molecules.And the dimmers are connected by weak interactions(2π…π,C—H…O;8π…π,O—H…O;12 C—H…π,O—H…O)to form 2D(2,8)and 3D(12)structure.For complexes 3,7 and 9 having similar ligands with different aldehydes,the molecules are connected to form 1D chain(3 and 7)byπ…πinteractions and to form 2D structure(9)by C—H…πinteractions.For complexes 3,4 and 5 of different metals with same ligands,the molecules are connected to form 1D structure byπ…π(3)and to 3D structure by C—H…πand N—H…O(4),C—H…πand N—H…O(5).For complexes 10 and 13 with the more rigid ligands comparision with 2,8 and 12,the packing mode are 3D(10 O—H…O,C—H…O,C—H…π)and 1D(π…πand Cu…O)by weak interactions.
For complexes(1,17 and 18)coordinated by sulfonamide,the molecules are connected to 2D structure by weak interactions,that is,N—H…O and C—H…πin 1, C—H…πand C—H…O in 17.
For complounds 18 and 20 in which the sulfonamide are not coordinate to metal, the molecules are connected to 2D by N—H…O hydrogen bonds and 3D by C—H…O hydrogen bonds,respectively.
Also complexes 6,16 and 19 are obtained as the tosyl breaking away the original ligands.The complexes are connected to 1D chain byπ…πinteractions for 6 and 16, and to 2D by N—H…Cl and O—H…O for 19.
Moreover,two dimensional(4,4)topology network were formed by weak interactions for compounds 5 and 19.
在第2和第3章中,以乙二胺为基础,合成了N-tosyl-乙二胺(Tsen),使其与水杨醛、5-溴水杨醛、2-羟基-1-萘醛以及吡啶甲醛反应,得到了4种磺酰胺Schiff碱配体,并以此为基础合成了它们的过渡金属配合物,得到了11个配合物的单晶,分别为[Cu(Tsen)_2](1)、[Cu(salTsen)(H_2O)](2)、[Cu(salTsen)_2](3)、[Ni(salTsen)_2](4)、[Zn(salTsen)_2]·H_2O(5)、[Cu(sal)(phen)]ClO_4(6)、[Cu(5-Brsal- Tsen)_2](7)、[Cu(5-BrsalTsen)(H_2O)](8)、[Cu(napnTsen)_2](9)、[Cu(naphTsen)(H_2O)]_2(10)和[Mn(pyTsen)_2Cl_2]·1.5H_2O(11)。
在第4章中,以1,2-丙二胺为基础,得到了一个Schiff碱配合物的单晶,[Cu(salTspn)(H_2O)](12)。以邻苯二胺为基础,得到了三个Schiff碱及其配合物,其中得到了一个配合物的单晶[Cu(salTsophan)(H_2O)](13)。
在第5章中,以二乙三胺为基础,得到了双磺酰化二乙三胺,与不同金属铜盐反应,得到了两个化合物的单晶,分别为[Cu_2(bisTsdeta)_2(H_2O)_2](17)和[Cu(mal)_2(bisTsdeta)_2·H_2O](18)。而反应条件改变时,还得到了磺酰基断裂的Schiff碱配合物[Cu(saldeta)(H_2O)]Cl(19)。以刚性的联苯胺为基础,得到了超分子化合物bisTsBZD·2DMF(20)。
对于磺酰胺席夫碱配体的配位模式来说,有负一价双齿HL·(3、4、5、7、9),负二价三齿L~(2-)(2、8、12、13)和负二价四齿μ_2桥联(10)三种。
对于配合物的结构来说,有磺酰基氧桥联的双核结构(10、17),酰胺或其席夫碱配位的单核结构(1、2、3、4、5、7、8、9、11、12、13),酰胺未配位的超分子结构(18、20)以及磺酰基断裂的单核配合物(6、16、19)。
从化合物的堆积模式来说,配合物2、8和12的配体具有相似的结构,其结构中都为螯合环与芳环间先以双重π…π作用形成双聚体,双聚体间以弱相互作用(2π…π和C—H…O,8π…π和O—H…O,12C—H…π和O—H…O)连接成二维(2、8)和三维结构(12):配合物3、7和9的配体中的醛不同,其分子间分别为π…π连成的一维链(3、7)和C—H…π形成的二维结构(9);配合物3、4、5的配体相同而金属离子不同,但分别以弱作用力(3π…π,4C—H…π,N—H…O和C—H…O,5C—H…π和N—H…O)堆积成一维(3)和三维结构(4、5);配合物10和13的配体相对于配合物2、8和12,刚性增强,则分别为弱作用力(10O—H…O、C—H…O和C—H…π,13π…π和Cu…O)形成的三维(10)和一维(13)结构。
磺酰胺的配合物1和17,均由弱作用力(1N—H…O和C—H…π:17C—H…π和C—H…O)连接成二维结构。
酰胺未配位的超分子化合物18和20,则分别为N—H…O连接成的二维结构与C—H…O连接成的三维结构。
磺酰基断裂残片的配合物6、16和19,分别为π…π形成的一维链(6、16)和N—H…Cl与O—H…O形成的二维结构(19)。
而且,化合物5和19中正是因为这些弱作用力的存在,形成了平面上的(4,4)拓扑结构。
In this paper,ethylenediamine,1,2-propanediamine,1,2-diaminobenzene, diethylenetriamine and benzidine were used as original materials based on sulfonamide and its Schiff base.5 sulfonamide and 8 sulfonamide Schiff base were obtained.20 compounds were prepared and 18 obtained as single crystals by general solution,microwave and electrochemical synthesis method.The obtained compounds were characterized by elemental analysis,X-ray single crystal diffraction,X-ray powder diffraction,IR,UV-Vis and TG-DSC.Moreover,some compounds were discussed by quantum chemistry results.
In chapter 2 and 3,N-tosyl-ethylenediamine(Tsen)were prepared and reacted with salicylaldehyde,5-Br-salicylaldehyde,2-hydroxy-1-naphthaldehyde and 2-pyridinealdehyde.4 sulfonamide Schiff base ligands were obtained and reacted with transitional metals.11 complexes as crystals were prepared,that is,[Cu(Tsen)_2](1), [Cu(salTsen)(H_2O)](2)、[Cu(salTsen)_2](3)、[Ni(salTsen)_2](4)、[Zn(salTsen)_2]·H_2O (5)、[Cu(sal)(phen)]ClO_4(6)、[Cu(5-BrsalTsen)_2](7)、[Cu(5-BrsalTsen)(H_2O)](8)、[Cu(napnTsen)_2](9)、[Cu(naphTsen)(H_2O)]_2(10)和[Mn(pyTsen)_2Cl_2]·1.5H_2O(11)。
In chapter 4,N-tosyl-propanediamine(Tspn)were prepared based on 1,2-propanediamine.And the corresponding Schiff base complex is obtained with the composition of[Cu(salTspn)(H_2O)](12).Also three Schiff base complexes based on N-tosyl-diaminebenzene(Tsophan)were prepared and one was obtained as single crystal with the composition of[Cu(salTsophan)(H_2O)](13).
In chapter 5,N,N"-tosyl-diethylenetriamine(BisTsdeta)were prepared based diethylenetriamine.Different compounds were obtained when BisTsdeta reacted with different metal salts,which are binuclear complex[Cu_2(bisTsdeta)_2(H_2O)_2](17)and supermolecule[Cu(mal)_2(bisTsdeta)_2·H_2O](18).Also complex[Cu(saldeta)(H_2O)]Cl (19)was obtained when the reaction condition changed.N,N'-Bistosylbenzidine (BistTsBZD)was obtained based on rigid benzidine,and the supermolecule BisTsBZD·2DMF(20)was obtained as single crystal.
There are three kinds of coordination mode of sulfonamide Schiff base,which are anionic bidentate HL~-(3,4,5,7,9),dianionic tridentate(2,8,12,13)and dianionicμ_2-bridged tetradentate(10).
For the structure of the compounds,there are binuclear structure bridged by the oxygen atom of tosyl group(10,17),mononuclear structure coordinated by sulfonamide or its Schiff base(1,2,3,4,5,7,8,9,11,12,13),supermolecule without the coordination of sulfonamide(18,20)and the monoclear complexes with the residue group in which the sulfonamide breaking in the iigand.
The supermolecule interactions are various in the crystal of the compounds.For complexes 2,8 and 12 having similar ligands,dimers are formed by the doubleπ…πinteractions between chelated ring and benzene ring of two molecules.And the dimmers are connected by weak interactions(2π…π,C—H…O;8π…π,O—H…O;12 C—H…π,O—H…O)to form 2D(2,8)and 3D(12)structure.For complexes 3,7 and 9 having similar ligands with different aldehydes,the molecules are connected to form 1D chain(3 and 7)byπ…πinteractions and to form 2D structure(9)by C—H…πinteractions.For complexes 3,4 and 5 of different metals with same ligands,the molecules are connected to form 1D structure byπ…π(3)and to 3D structure by C—H…πand N—H…O(4),C—H…πand N—H…O(5).For complexes 10 and 13 with the more rigid ligands comparision with 2,8 and 12,the packing mode are 3D(10 O—H…O,C—H…O,C—H…π)and 1D(π…πand Cu…O)by weak interactions.
For complexes(1,17 and 18)coordinated by sulfonamide,the molecules are connected to 2D structure by weak interactions,that is,N—H…O and C—H…πin 1, C—H…πand C—H…O in 17.
For complounds 18 and 20 in which the sulfonamide are not coordinate to metal, the molecules are connected to 2D by N—H…O hydrogen bonds and 3D by C—H…O hydrogen bonds,respectively.
Also complexes 6,16 and 19 are obtained as the tosyl breaking away the original ligands.The complexes are connected to 1D chain byπ…πinteractions for 6 and 16, and to 2D by N—H…Cl and O—H…O for 19.
Moreover,two dimensional(4,4)topology network were formed by weak interactions for compounds 5 and 19.
引文
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