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Acta Physico-Chimica Sinica  2006, Vol. 22 Issue (07): 797-803    DOI: 10.3866/PKU.WHXB20060706
Article     
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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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: 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. Acta Physico-Chimica Sinica, 2006, 22(07): 797-803.

URL:

http://www.whxb.pku.edu.cn/Jwk_wk/wlhx/10.3866/PKU.WHXB20060706     OR     http://www.whxb.pku.edu.cn/Jwk_wk/wlhx/Y2006/V22/I07/797

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