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ISSN 1000-6818CN 11-1892/O6CODEN WHXUEU
Acta Phys Chim Sin >> 2006,Vol.22>> Issue(07)>> 797-803     doi: 10.3866/PKU.WHXB20060706         中文摘要
Density Functional Studies on Formamide′s Water-influenced Proton Transfer in Solution
LIANG Wan-Chun;LI Hao-Ran;HU Xing-Bang;HAN Shi-Jun
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
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The interconversion process between keto and enol forms of formamide (FM→FA) can be regarded as a model for tautomerization of larger nucleic acid base, which may be responsible for the spontaneous point mutation in DNA. The present paper describes a study of structural tautomer interconversion and the relative stabilizing influences of water for formamide-H2O and the enol form formamidic acid-H2O in aqueous solution. The solvent effects were considered by explicit water molecule within SCRF framework. In the vicinity of formamide (FM) and formamidic acid (FA), three different regions are considered, full geometry optimizations of these complexes were carried out at B3LYP/6-311++G** using self-consistent isodensity polarized continuum model (SCIPCM). The calculated results indicate that water in two of them can protect formamide from tautomerizing, while in the third one works oppositely, exactly the same as the situations in gas phase. However, comparing with the transition in gas phase, the protective and assistive effects induced by the explicit water are greatly altered. The calculated results shed more light on the water′s influence on the proton transfer and offer a new insight into the structural tautomer interconversion of FM.

Keywords: Formamide   Tautomerization   Water-influenced   Proton transfer   SCIPCM  
Received: 2006-01-10 Accepted: 2006-02-22 Publication Date (Web): 2006-06-27
Corresponding Authors: LI Hao-Ran Email: lihr@zju.edu.cn


Cite this article: LIANG Wan-Chun;LI Hao-Ran;HU Xing-Bang;HAN Shi-Jun. Density Functional Studies on Formamide′s Water-influenced Proton Transfer in Solution[J]. Acta Phys. -Chim. Sin., 2006,22 (07): 797-803.    doi: 10.3866/PKU.WHXB20060706
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21. XU Xiao-Fang, GAO Fang, LI Hong-Ru, ZHANG Sheng-Tao.Excited State Intramolecular Proton Transfer of a Chromophore Linked to Benzotriazole Derivatives[J]. Acta Phys. -Chim. Sin., 2010,26(01): 131-140
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24. ZHU Yue, PU Min, HE Jing, EVANS David G..Photoisomerization Mechanism of the Trans-cis Azobenzene Sulphonate Derivatives[J]. Acta Phys. -Chim. Sin., 2009,25(11): 2296-2304
25. XU Si-Chuan, MA Li-Ying, BIAN Fu-Yong, SHI Qiang, GE Mao-Fa, ZHANG Xing-Kang.H2O-Coupled Proton Transfer Mechanism and Hydrogen Tunneling Effects in the Reaction of H2NCH2CN with H2O in the Interstellar Medium[J]. Acta Phys. -Chim. Sin., 2009,25(11): 2312-2318
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28. WANG Luo-Xin; TUO Xin-Lin; XU Jie; LI Song-Nian; WANG Xiao-Gong.Effect of Trans-Cis Isomerization on the Sensitivity of Energetic Azo-Compounds[J]. Acta Phys. -Chim. Sin., 2008,24(10): 1756-1760
29. LIU Min; ZHU Lan-Ying; LI Bin; ZHAO Qiang; SUN De-Zhi; LIN Rui-Sen.Thermodynamics of Dilution of N,N-Dimethylformamide in Aqueous Sodium Chloride Solutions at Different Concentrations[J]. Acta Phys. -Chim. Sin., 2008,24(07): 1316-1320
30. SHEN Qiu-Chan; LIANG Wan-Chun; HU Xing-Bang; LI Hao-Ran.Molecular Dynamics Simulation for Formamide Aqueous Solution[J]. Acta Phys. -Chim. Sin., 2008,24(07): 1169-1174
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39. ZHOU Jun-Hong; ZENG Yan-Li; ZHANG Xue-Ying; MENG Ling-Peng; ZHENG Shi-Jun.Reaction Mechanisms and Topological Studies of Electron Density for IClO2 Isomerization[J]. Acta Phys. -Chim. Sin., 2007,23(08): 1229-1234
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42. ZHANG Shu-Qiang;WANG Ya-Qiong;ZHENG Xu-Ming.Density Functional Theory Investigation of the Photoisomerization Reaction of Nitroalkanes and Nirroaromatic Compounds[J]. Acta Phys. -Chim. Sin., 2006,22(12): 1489-1494
43. LI Wen-Zuo;GONG Bao-An;CHENG Jian-Bo.DFT Study on the Unsaturated Silylenoid H2C=SiNaF[J]. Acta Phys. -Chim. Sin., 2006,22(06): 653-656
44. HU Xing-bang; LI Hao-ran; LIANG Wan-chun; HAN Shi-jun.Explore the Effect Induced by Water in the Proton Transfer Process of 5-fluorouracil[J]. Acta Phys. -Chim. Sin., 2005,21(09): 952-956
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46. Xu Bo;Li Hao-Ran;Wang Cong-Min;Han Shi-Jun.Correlation of 1H NMR for Alcohol+DMF Systems Based on SAFT[J]. Acta Phys. -Chim. Sin., 2003,19(11): 1059-1063
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50. Zhang Li;Zhang Dong-Bai;Ma Ji-Ming;Cheng Hu-Min;Qi Li-Min.The Solubilization and Conductivity Properties of Nonaqueous Reverse Microemulsion[J]. Acta Phys. -Chim. Sin., 2003,19(02): 120-124
51. Wang Yu;He Feng-Rong;Liu Guan-Kun;Chen Liu-Ping;Tong Ye-Xiang.Electrical Conductivity of Four Neodymium Salts in Dimethylformamide[J]. Acta Phys. -Chim. Sin., 2002,18(09): 850-854
52. Yu Hai-Tao;Chi Yu-Juan;Fu Hong-Gang;Huang Xu-Ri;Sun Jia-Zhong.The Structures and Relative Stabilities of HBO2 Isomers[J]. Acta Phys. -Chim. Sin., 2002,18(01): 87-90
53. Wang Yu;Liu Guan-Kun;He Feng-Rong;Tong Ye-Xiang.Electrodeposition of Ho-Ni Alloy from Dimethyformamide Bath[J]. Acta Phys. -Chim. Sin., 2001,17(03): 206-209
54. Shi Tu-Jin, Liu Li, Yang Da-Lin, Zhu Qi-He.Ab initio Study on Hydrogen Bonding Clusters between 1,4-dioxane and Ammonia[J]. Acta Phys. -Chim. Sin., 2000,16(05): 416-421
55. Zhang Wen-Qin, Zhang Zhi-Ming, Zheng Yan, Wang Shu-Li, Zhao Shu-Na.Crystal Structure and Photochemical Properties of r-1,c-2,t-3,t-4-1,3-bis(4-biphenyl)-2,4-di(4-pyridyl)cyclobutane[J]. Acta Phys. -Chim. Sin., 2000,16(03): 207-213
56. Bai Tong-Chun, Han Shi-Jun, Tang Qing-Hu, Lu Yan, Lu Jin-Suo.Volumetric Properties of Glucose,Fructose and Sucrose in Formamide[J]. Acta Phys. -Chim. Sin., 1998,14(10): 898-905
57. Hu Hai-Quan.Mechanism of the Isomerization of Nitryl Hydride[J]. Acta Phys. -Chim. Sin., 1998,14(06): 544-547
58. Hu Hai-Quan, Liu Cheng-Bu.Mechanism of the Isomerization of Difluorosilacyclopropene[J]. Acta Phys. -Chim. Sin., 1998,14(04): 349-352
59. Xu Wen-Yuan,Hong San-Guo,Peng Yi-Yuan,Li Yong-Hong,Wang Sheng.Quantum Chemical Study on the Tautomeric Reaction of p -R-phenyltetrazoles[J]. Acta Phys. -Chim. Sin., 1997,13(12): 1115-1118
60. Ke Jie,Lu Jie,Zhong Ming-Hong,Zou Lei,Han Bu-Xing,Yan Hai-Ke.Effect of Ethanol on the Tautomerism of Ethyl Acetoacetate in Supercritical CO2[J]. Acta Phys. -Chim. Sin., 1997,13(04): 351-353
61. Li Ze-Min,Wu Shi-Kang.Study on Photophysical Behaviors of Styryl Pyrazine Derivatives[J]. Acta Phys. -Chim. Sin., 1996,12(05): 418-422
62. Wang Xue-Song,Zhang Bao-Wen,Cao Yi.A Mechanism Study of Sensitized Photoisomerization of Norbornadiene Derivatives[J]. Acta Phys. -Chim. Sin., 1996,12(05): 423-428
63. Liu Tian-Jun,Wu Shi-Kang.The Photoisomerization of Azobenzene for Regulating the Complex Behavior of Viologen with Eosin[J]. Acta Phys. -Chim. Sin., 1996,12(04): 329-336
64. Xu Zong-Rong,Tian Zhi-Yue.The Quantum Theory of Reactive Rate for Isomerization Photochemical Reaction[J]. Acta Phys. -Chim. Sin., 1995,11(08): 762-765
65. Gao Zi, Hua Wei-Ming, Chen Jian-Min, Tang Yi.Characterization of Solid Superacidity by Pentane Isomerization Reaction[J]. Acta Phys. -Chim. Sin., 1994,10(10): 897-902
66. Gao Zi, Chen Jian-Min, Tang Yi, Hua Wei-Ming.Characterization of Solid Superacidity by Butane Isomerization Reaction at Ambient Temperature[J]. Acta Phys. -Chim. Sin., 1994,10(08): 698-703
67. Yan Zheng-Lin, Wu Shi-Kang.The Photophysical Behavior of 2-Pyrazoline with Azastilbene[J]. Acta Phys. -Chim. Sin., 1994,10(07): 610-615
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69. Zhou Xiao-Hai, Zhang Shao-Hui, Huang Su-Qiu, Qu Song-Sheng.Thermodnamics of Oxygen Binding to Dicobalt Diporphyrin in N,N-Dimethylformamide[J]. Acta Phys. -Chim. Sin., 1994,10(05): 391-395
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71. Sun Hong-Zhe; Li Cun; Yao Yi-Ming; Fang Qi; You Xiao-Ceng.NMR Studies of the Isomer Conversion of Formanilide[J]. Acta Phys. -Chim. Sin., 1993,9(01): 117-120
72. Ma Si-Yu; Feng Wen-Lin.Theoretical Study on the Tautomeric Reaction of Acetaldehyde Into Vinyl Alcohol and Ketene Into Ethynol[J]. Acta Phys. -Chim. Sin., 1992,8(05): 654-658
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