Insight of the Structures and Properties on 2-Thioxanthine Complexes with One Hg~(2+) and Two Cl~- Ions:a Theoretical Investigation
|
摘要
The molecular structures of fifteen possible 2-thioxanthine(2TX) complexes with one Hg~(2+) and two Cl-ions were fully optimized using density functional theory B3PW91/6-311++G** method. The effective pseudo potential LANL2DZ basis set was used for metal Hg~(2+)ion. The vibrational analysis was also carried out at the same level. The bond lengths, bond angles, zero point energies, Gibbs free energies, thermodynamic energies and relative energies of all the complexes were obtained. The NBO analysis for natural charge and the second order perturbation energy values was carried out for three stable complexes and the IR spectroscopy of the two complexes was assigned to the experimental data. The results show that the 2-thioxanthine complexes with one Hg~(2+) and two Cl-ions were formed and the complexes resulting from the thione tautomer are more stable than that of the thiol ones. The order of three complexes with relative lower energy is 2TX(1,3,7)-Hg~(2+)-2, 2 TX(1,3,7)-Hg~(2+)-1 and 2 TX(1,3,9)-Hg~(2+). The calculated IR spectroscopy of the two complexes agreed with the experimental data.
The molecular structures of fifteen possible 2-thioxanthine(2TX) complexes with one Hg~(2+) and two Cl-ions were fully optimized using density functional theory B3PW91/6-311++G** method. The effective pseudo potential LANL2DZ basis set was used for metal Hg~(2+)ion. The vibrational analysis was also carried out at the same level. The bond lengths, bond angles, zero point energies, Gibbs free energies, thermodynamic energies and relative energies of all the complexes were obtained. The NBO analysis for natural charge and the second order perturbation energy values was carried out for three stable complexes and the IR spectroscopy of the two complexes was assigned to the experimental data. The results show that the 2-thioxanthine complexes with one Hg~(2+) and two Cl-ions were formed and the complexes resulting from the thione tautomer are more stable than that of the thiol ones. The order of three complexes with relative lower energy is 2TX(1,3,7)-Hg~(2+)-2, 2 TX(1,3,7)-Hg~(2+)-1 and 2 TX(1,3,9)-Hg~(2+). The calculated IR spectroscopy of the two complexes agreed with the experimental data.
The molecular structures of fifteen possible 2-thioxanthine(2TX) complexes with one Hg~(2+) and two Cl-ions were fully optimized using density functional theory B3PW91/6-311++G** method. The effective pseudo potential LANL2DZ basis set was used for metal Hg~(2+)ion. The vibrational analysis was also carried out at the same level. The bond lengths, bond angles, zero point energies, Gibbs free energies, thermodynamic energies and relative energies of all the complexes were obtained. The NBO analysis for natural charge and the second order perturbation energy values was carried out for three stable complexes and the IR spectroscopy of the two complexes was assigned to the experimental data. The results show that the 2-thioxanthine complexes with one Hg~(2+) and two Cl-ions were formed and the complexes resulting from the thione tautomer are more stable than that of the thiol ones. The order of three complexes with relative lower energy is 2TX(1,3,7)-Hg~(2+)-2, 2 TX(1,3,7)-Hg~(2+)-1 and 2 TX(1,3,9)-Hg~(2+). The calculated IR spectroscopy of the two complexes agreed with the experimental data.
引文
[1]Wang,Z.;Rana,T.M.RNA conformation in the Tat-TAR complex determined by site-specific photo-cross-linking.Biochemistry 1996,32,6491-6499.
(2)Speina,E.;Cie?la,J.M.;Grziewicz,J.M.;Laval,J.;Kazimierczuk,Z.;Tudek,B.Inhibition of DNA repair glycosylases by base analogs and tryptophan pyrolysate,Trp-P1.Acta Biochim.Polon.2005,52,167-178.
(3)Darensbourg,D.J.;Frost,B.J.;Derecskei,K.A.;Reibenspies,J.H.Coordination chemistry,structure,and reactivity of thiouracil derivatives of tungsten(0)hexacarbonyl:a theoretical and experimental investigation into the chelation/dechelation of thiouracil via CO loss and addition.Inorg.Chem.1999,38,4715-4723.
(4)Dafali,A.;Hammouti,B.;Mokhlisse,R.;Kertit,S.Substituted uracils as corrosion inhibitors for copper in 3%Na Cl solution.Corrosion Sci.2003,45,1619-1630.
(5)Nielsen,O.H.;Vainer,B.;Rask,M.J.The treatment of inflammatory bowel disease with 6-mercaptopurine or azathioprine.Aliment.Pharmacol.Ther.2001,15,1699-1708.
(6)Neunert,C.E.;Buchanan,G.R.6-Mercaptopurine:teaching an old drug newtricks.Pediatr.Blood.Cancer.2009,52,5-6.
(7)Kulikowska,E.;Kierdaszuk,B.;Shugar,D.Xanthine,xanthosine and its nucleotides:solution structures of neutral and Ionic forms,and relevance to substrate properties in various enzyme systems and metabolic pathways.Acta Biochim.Polon.2004,51,493-531.
(8)Stoychev,G.;Kierdaszuk,B.;Shugar,D.Xanthosine and xanthine substrate properties with purine nucleoside phosphorylases and relevance to other enzyme systems.Eur.J.Biochem.2002,269,4048-4057.
(9)Tamta,H.;Kalra,S.;Thilagavathi,R.;Chakraborti,A.K.;Mukhopadhyay,A.K.Nature and position of functional group on thiopurine substrates influence activity of xanthine oxidase-enzymatic reaction pathways of 6-mercaptopurine and 2-mercaptopurine are different.Biochemistry 2007,72,170-177.
(10)Papakostas,K.;Georgopoulou,E.;Frillingos,S.Cysteine-scanning analysis of putative helix XII in the Ygf Oxanthine permease.J.Biol.Chem.2008,283,13666-13678.
(11)Mautner,H.G.;Bergson,G.Some remarks on position-conditioned differences of the ultraviolet spectra and chemical reactivities of disubstituted pyrimidines and purines.Acta Chem.Scand.1963,17,1694-1704.
(12)Twanmoh,L.M.;Wood,H.B.;Driscoll,J.S.NMR spectral characteristics of N-H protons in purine derivatives.J.Heterocycl.Chem.1973,10,187-190.
(13)Civcir,P.U.Tautomerism of 2-thioxanthine in the gas and aqueous phases using AM1 and PM3 methods.J.Mol.Struct.(Theochem).2001,546,163-173.
(14)Li,B.Z.Density functional theory calculation on 2-thioxanthine tautomers.Acta Phys.Chim.Sin.2004,20,1455-1458.
(15)Yuan,X.X.;Wang,Y.F.;Wang,X.;Chen,W.B.;Fossey,J.S.;Wong,N.B.An ab initio and AIM investigation into the hydration of 2-thioxanthine.Chem.Central.J.2010,4,1-19.
(16)Sanchez,M.P.;Salas-Peregrin,J.M.;Romero-Molina,M.A.Thermal studies on purine complexes XI.Thermal behaviour of 2-TI-II oxanthine,its chloroydrate and some thioxanthine complexes of Ag(I),Cd(II),Hg(II)and Hg(I).Thermochimica.Acta 1986,102,149-162.
(17)Sánchez-Sánchez,M.P.;Salas-Peregrin,J.M.;Romero-Molina,M.A.;Mata-Arjona,A.Stability and thermo hdynamic parameters of thiopyrimidines,2-thioxanthine and their complexes with Zn(II)and Cd(II).Thermochimica Acta 1985,88,355-361.
(18)Rosenberg,B.;Van Camp,L.;Trosko,J.E.;Hansour,V.H.Platinum compounds:a new class of potent antitumor agents.Nature 1969,222,385-386.
(19)Rosenberg,B.Possible mechanisms for the antitumor activity of platinum coordination complexes.Cancer Chemother Rep.1975,59,589-598.
(20)Frisch,M.J.;Trucks,G.W.;Schlegel,H.B.;Scuseria,G.E.;Robb,M.A.;Cheeseman,J.R.;Scalmani,G.;Barone,V.;Mennucci,B.;Petersson,G.A.;Nakatsuji,H.;Caricato,M.;Li,X.;Hratchian,H.P.;Izmaylov,A.F.;Bloino,J.;Zheng,G.;Sonnenberg,J.L.;Hada,M.;Ehara,M.;Toyota,K.;Fukuda,R.;Hasegawa,J.;Ishida,M.;Nakajima,T.;Honda,Y.;Kitao,O.;Nakai,H.;Vreven,T.;Montgomery,J.A.Jr.;Peralta,J.E.;Ogliaro,F.;Bearpark,M.;Heyd,J.J.;Brothers,E.;Kudin,K.N.;Staroverov,V.N.;Kobayashi,R.;Normand,J.;Raghavachari,K.;Rendell,A.;Burant,J.C.;Iyengar,S.S.;Tomasi,J.;Cossi,M.;Rega,N.;Millam,J.M.;Klene,M.;Knox,J.E.;Cross,J.B.;Bakken,V.;Adamo,C.;Jaramillo,J.;Gomperts,R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.;Ochterski,J.W.;Martin,R.L.;Orokuma,K.;Zakrzewski,V.G.;Voth,G.A.;Salvador,P.;Dannenberg,J.J.;Dapprich,S.;Daniels,A.D.;Farkas,O.;Foresman,J.B.;Ortiz,J.V.;Cioslowsk,J.;Fox,D.J.Gaussian 09,Revision A.02,Gaussian In.,Wallingford CT 2009.
(21)Becke,A.D.A new mixing of hartree-fock and local densityfunctional theories.J.Chem.Phys.1993,98,1372-1377.
(22)Su,K.H.;Wei,J.;Hu,X.L.;Yue,H.;Lv,L.;Wang,Y.B.;Wen,Z.Y.Systematic comparison of geometry optimization on inorganic molecules.Acta Phys.Chim.Sin.2000,16,643-650.
(23)Xu,Z.G.;Gu,G.B.;Liu,H.Y.;Jiang,H.F.;Chang,C.K.Ab-initio and DFT calculations of Pd Cl2L2(L=DHSO,DPSO)complexes.Chin.J.Struct.Chem.2006,25,1524-1530.
(24)Abolfazl,S.;Ehsan,Z.Thermal decomposition kinetics of ethane Halides and derivatives(C2H6-n Xn(n=1~3);X=F,Cl,Br):DFT study and NBO analysis.Chin.J.Struct.Chem.2011,30,858-866.
(25)Glendening,E.D.;Reed,A.E.;Carpenter,J.E.;Weinhold,F.NBO Version 3.1 Gaussian 09,Revision A.02,Gaussian In.,Wallingford CT 2009.
(26)Mezey,P.G.;Ladik,J.J.A non-empirical molecular orbital study on the relative stabilities of adenine and guanine tautomers.Theor.Chim.Acta1979,2,129-145.
(27)Mezey,P.G.;Ladik,J.J.;Barry,M.Non-empirical SCF MO studies on the protonation of biopolymer constituents.ⅡProtonation of adenine,guanine and their tautomeric forms.Theor.Chim.Acta 1980,54,251-258.
(28)Steckel,J.A.Ab initio modeling of neutral and cationic Hg-benzene complexes.Chem.Phys.Lett.2005,409,322-330.
(29)Zhang,Y.;Pan,Q.J.;Guo,Y.R.;Fu,H.G.;Zhang H.X.Theoretical investigation of ground-and excited-state properties of fluorenone-alkynyl Hg(II)complexes:the tuning of electronic spectroscopy.J.Mol.Struct.(Theochem.)2009,907,41-45.
(30)Hamid,R.K.;Anita,A.;Vahid,A.Synthesis,characterization and crystal structure determination of zinc(II)and mercury(II)complexes with2,2?-dimethyl-4,4?-bithiazole.Polyhedron 2008,27,1848-1854.
(2)Speina,E.;Cie?la,J.M.;Grziewicz,J.M.;Laval,J.;Kazimierczuk,Z.;Tudek,B.Inhibition of DNA repair glycosylases by base analogs and tryptophan pyrolysate,Trp-P1.Acta Biochim.Polon.2005,52,167-178.
(3)Darensbourg,D.J.;Frost,B.J.;Derecskei,K.A.;Reibenspies,J.H.Coordination chemistry,structure,and reactivity of thiouracil derivatives of tungsten(0)hexacarbonyl:a theoretical and experimental investigation into the chelation/dechelation of thiouracil via CO loss and addition.Inorg.Chem.1999,38,4715-4723.
(4)Dafali,A.;Hammouti,B.;Mokhlisse,R.;Kertit,S.Substituted uracils as corrosion inhibitors for copper in 3%Na Cl solution.Corrosion Sci.2003,45,1619-1630.
(5)Nielsen,O.H.;Vainer,B.;Rask,M.J.The treatment of inflammatory bowel disease with 6-mercaptopurine or azathioprine.Aliment.Pharmacol.Ther.2001,15,1699-1708.
(6)Neunert,C.E.;Buchanan,G.R.6-Mercaptopurine:teaching an old drug newtricks.Pediatr.Blood.Cancer.2009,52,5-6.
(7)Kulikowska,E.;Kierdaszuk,B.;Shugar,D.Xanthine,xanthosine and its nucleotides:solution structures of neutral and Ionic forms,and relevance to substrate properties in various enzyme systems and metabolic pathways.Acta Biochim.Polon.2004,51,493-531.
(8)Stoychev,G.;Kierdaszuk,B.;Shugar,D.Xanthosine and xanthine substrate properties with purine nucleoside phosphorylases and relevance to other enzyme systems.Eur.J.Biochem.2002,269,4048-4057.
(9)Tamta,H.;Kalra,S.;Thilagavathi,R.;Chakraborti,A.K.;Mukhopadhyay,A.K.Nature and position of functional group on thiopurine substrates influence activity of xanthine oxidase-enzymatic reaction pathways of 6-mercaptopurine and 2-mercaptopurine are different.Biochemistry 2007,72,170-177.
(10)Papakostas,K.;Georgopoulou,E.;Frillingos,S.Cysteine-scanning analysis of putative helix XII in the Ygf Oxanthine permease.J.Biol.Chem.2008,283,13666-13678.
(11)Mautner,H.G.;Bergson,G.Some remarks on position-conditioned differences of the ultraviolet spectra and chemical reactivities of disubstituted pyrimidines and purines.Acta Chem.Scand.1963,17,1694-1704.
(12)Twanmoh,L.M.;Wood,H.B.;Driscoll,J.S.NMR spectral characteristics of N-H protons in purine derivatives.J.Heterocycl.Chem.1973,10,187-190.
(13)Civcir,P.U.Tautomerism of 2-thioxanthine in the gas and aqueous phases using AM1 and PM3 methods.J.Mol.Struct.(Theochem).2001,546,163-173.
(14)Li,B.Z.Density functional theory calculation on 2-thioxanthine tautomers.Acta Phys.Chim.Sin.2004,20,1455-1458.
(15)Yuan,X.X.;Wang,Y.F.;Wang,X.;Chen,W.B.;Fossey,J.S.;Wong,N.B.An ab initio and AIM investigation into the hydration of 2-thioxanthine.Chem.Central.J.2010,4,1-19.
(16)Sanchez,M.P.;Salas-Peregrin,J.M.;Romero-Molina,M.A.Thermal studies on purine complexes XI.Thermal behaviour of 2-TI-II oxanthine,its chloroydrate and some thioxanthine complexes of Ag(I),Cd(II),Hg(II)and Hg(I).Thermochimica.Acta 1986,102,149-162.
(17)Sánchez-Sánchez,M.P.;Salas-Peregrin,J.M.;Romero-Molina,M.A.;Mata-Arjona,A.Stability and thermo hdynamic parameters of thiopyrimidines,2-thioxanthine and their complexes with Zn(II)and Cd(II).Thermochimica Acta 1985,88,355-361.
(18)Rosenberg,B.;Van Camp,L.;Trosko,J.E.;Hansour,V.H.Platinum compounds:a new class of potent antitumor agents.Nature 1969,222,385-386.
(19)Rosenberg,B.Possible mechanisms for the antitumor activity of platinum coordination complexes.Cancer Chemother Rep.1975,59,589-598.
(20)Frisch,M.J.;Trucks,G.W.;Schlegel,H.B.;Scuseria,G.E.;Robb,M.A.;Cheeseman,J.R.;Scalmani,G.;Barone,V.;Mennucci,B.;Petersson,G.A.;Nakatsuji,H.;Caricato,M.;Li,X.;Hratchian,H.P.;Izmaylov,A.F.;Bloino,J.;Zheng,G.;Sonnenberg,J.L.;Hada,M.;Ehara,M.;Toyota,K.;Fukuda,R.;Hasegawa,J.;Ishida,M.;Nakajima,T.;Honda,Y.;Kitao,O.;Nakai,H.;Vreven,T.;Montgomery,J.A.Jr.;Peralta,J.E.;Ogliaro,F.;Bearpark,M.;Heyd,J.J.;Brothers,E.;Kudin,K.N.;Staroverov,V.N.;Kobayashi,R.;Normand,J.;Raghavachari,K.;Rendell,A.;Burant,J.C.;Iyengar,S.S.;Tomasi,J.;Cossi,M.;Rega,N.;Millam,J.M.;Klene,M.;Knox,J.E.;Cross,J.B.;Bakken,V.;Adamo,C.;Jaramillo,J.;Gomperts,R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.;Ochterski,J.W.;Martin,R.L.;Orokuma,K.;Zakrzewski,V.G.;Voth,G.A.;Salvador,P.;Dannenberg,J.J.;Dapprich,S.;Daniels,A.D.;Farkas,O.;Foresman,J.B.;Ortiz,J.V.;Cioslowsk,J.;Fox,D.J.Gaussian 09,Revision A.02,Gaussian In.,Wallingford CT 2009.
(21)Becke,A.D.A new mixing of hartree-fock and local densityfunctional theories.J.Chem.Phys.1993,98,1372-1377.
(22)Su,K.H.;Wei,J.;Hu,X.L.;Yue,H.;Lv,L.;Wang,Y.B.;Wen,Z.Y.Systematic comparison of geometry optimization on inorganic molecules.Acta Phys.Chim.Sin.2000,16,643-650.
(23)Xu,Z.G.;Gu,G.B.;Liu,H.Y.;Jiang,H.F.;Chang,C.K.Ab-initio and DFT calculations of Pd Cl2L2(L=DHSO,DPSO)complexes.Chin.J.Struct.Chem.2006,25,1524-1530.
(24)Abolfazl,S.;Ehsan,Z.Thermal decomposition kinetics of ethane Halides and derivatives(C2H6-n Xn(n=1~3);X=F,Cl,Br):DFT study and NBO analysis.Chin.J.Struct.Chem.2011,30,858-866.
(25)Glendening,E.D.;Reed,A.E.;Carpenter,J.E.;Weinhold,F.NBO Version 3.1 Gaussian 09,Revision A.02,Gaussian In.,Wallingford CT 2009.
(26)Mezey,P.G.;Ladik,J.J.A non-empirical molecular orbital study on the relative stabilities of adenine and guanine tautomers.Theor.Chim.Acta1979,2,129-145.
(27)Mezey,P.G.;Ladik,J.J.;Barry,M.Non-empirical SCF MO studies on the protonation of biopolymer constituents.ⅡProtonation of adenine,guanine and their tautomeric forms.Theor.Chim.Acta 1980,54,251-258.
(28)Steckel,J.A.Ab initio modeling of neutral and cationic Hg-benzene complexes.Chem.Phys.Lett.2005,409,322-330.
(29)Zhang,Y.;Pan,Q.J.;Guo,Y.R.;Fu,H.G.;Zhang H.X.Theoretical investigation of ground-and excited-state properties of fluorenone-alkynyl Hg(II)complexes:the tuning of electronic spectroscopy.J.Mol.Struct.(Theochem.)2009,907,41-45.
(30)Hamid,R.K.;Anita,A.;Vahid,A.Synthesis,characterization and crystal structure determination of zinc(II)and mercury(II)complexes with2,2?-dimethyl-4,4?-bithiazole.Polyhedron 2008,27,1848-1854.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |