Please wait a minute...
Acta Physico-Chimica Sinica  2006, Vol. 22 Issue (07): 797-803    DOI: 10.3866/PKU.WHXB20060706
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
Download:   PDF(341KB) Export: BibTeX | EndNote (RIS)      

Abstract  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.

Key wordsFormamide      Tautomerization      Water-influenced      Proton transfer      SCIPCM     
Received: 10 January 2006      Published: 27 June 2006
Corresponding Authors: LI Hao-Ran     E-mail:
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. Acta Physico-Chimica Sinica, 2006, 22(07): 797-803.

URL:     OR

[1] XIANG Jun-Feng, YI Ping-Gui, REN Zhi-Yong, YU Xian-Yong, CHEN Jian, LIU Wu, LI Tao-Mei. Effect of Supra-Molecular Interaction on the Intramolecular Proton Transfer of 2-(2-Aminophenyl)benzothiazole[J]. Acta Physico-Chimica Sinica, 2016, 32(3): 624-630.
[2] ZHAO Jun-Feng, SUN Xiao-Li, LI Ji-Lai, HUANG Xu-Ri. Theoretical Study of Methanol C―H and O―H Bond Activation by PtRu Clusters[J]. Acta Physico-Chimica Sinica, 2015, 31(6): 1077-1085.
[3] SU Ya-Qiong, WU De-Yin, TIAN Zhong-Qun. Density Functional Theory Calculations of the Influence of Weak Hydrogen Bonding Interactions on the Raman Spectra of Thiourea in Aqueous Solution[J]. Acta Physico-Chimica Sinica, 2014, 30(11): 1993-1999.
[4] WANG Xiao-Xuan, HU Wei, GUI Da-Yong, CHI Xu-Hui, WANG Ming-Liang, TIAN De-Yu, LIU Jian-Hong, MA Xin-Gang, PANG Ai-Min. Proton Transfer in Reaction between 2,4-Diisocyanatotoluene and Amine Compounds[J]. Acta Physico-Chimica Sinica, 2014, 30(1): 34-42.
[5] CHENG Wei-Na, HU Xin-Gen, SHAO Shuang. Macrocyclic Hydrophobic Effect:Enthalpic Pairwise Interactions of Crown Ethers in Mixtures of DMF and Water[J]. Acta Physico-Chimica Sinica, 2013, 29(10): 2114-2122.
[6] LIN Yue-Xia, WANG Hong-Yan, GAO Si-Min, WU Ying-Xi, LI Ru-Hu. Double-Proton-Transfer Reaction in Guanine-Cytosine Base Pair Embedded in B-Form DNA[J]. Acta Physico-Chimica Sinica, 2013, 29(06): 1233-1239.
[7] ZHOU Zi-Yan, LIU Min, SU Zhong-Min, XIE Yu-Zhong, DING Shen-De, WANG Hua-Jing. Proton-Transfer Isomerization Reactions of 2-(2-Hydroxybenzylidenamino)pyrimidine-4,6-diol[J]. Acta Physico-Chimica Sinica, 2011, 27(09): 2035-2042.
[8] NIE Hong-Qian, HOU Wan-Guo. Methods and Applications for Delamination of Layered Double Hydroxides[J]. Acta Physico-Chimica Sinica, 2011, 27(08): 1783-1796.
[9] SONG Lei, YU Feng, WU Li-Xia, ZHOU Xiao-Guo, LIU Shi-Lin. Anionic Production Pathways Involved in the Reaction between OH- and CH2ClF[J]. Acta Physico-Chimica Sinica, 2011, 27(04): 801-807.
[10] SHI Jun-You, DONG Li-Hua, LIU Yong-Jun. Effect of Hydroxylation on Structures and Proton Transfer of A-T Base Pairs[J]. Acta Physico-Chimica Sinica, 2010, 26(12): 3329-3336.
[11] XUE Liang, ZHAO Feng-Qi, XING Xiao-Ling, GAO Hong-Xu, YI Jian-Hua, HU Rong-Zu. Dissolution Properties of 1,3,3-Trinitroazetidine in Ethyl Acetate and N,N-Dimethylformamide[J]. Acta Physico-Chimica Sinica, 2009, 25(12): 2413-2416.
[12] 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 Physico-Chimica Sinica, 2009, 25(11): 2312-2318.
[13] DUAN Jun-Yuan, ZHANG Qiao-Xin, WANG Yi-Long, GUAN Jian-Guo. Facile Synthesis and Formation Mechanism of Silver Nanoplates with Edge Lengths of Several Micrometers[J]. Acta Physico-Chimica Sinica, 2009, 25(07): 1405-1408.
[14] ZHU Ting-Liang; LI Gui-An; YE Lu-Yuan; DENG Zhong-Xun; WANG Peng-Fei. Effect of DMF and Heat Treatment on the Copper-Doped Silica Nanocomposite Aerogel Prepared by Ambient Drying[J]. Acta Physico-Chimica Sinica, 2009, 25(01): 126-130.
[15] SHEN Qiu-Chan; LIANG Wan-Chun; HU Xing-Bang; LI Hao-Ran. Molecular Dynamics Simulation for Formamide Aqueous Solution[J]. Acta Physico-Chimica Sinica, 2008, 24(07): 1169-1174.