Solvent-mediated tautomerization of purine: single to quadruple proton transfer

被引:51
作者
Ahn, DS
Lee, S [1 ]
Kim, B
机构
[1] Kyung Hee Univ, Coll Environm Sci & Appl Chem BK21, Yongin 449701, Kyungki Do, South Korea
[2] Korea Adv Inst Sci & Technol, Dept Chem BK21, Taejon 305701, South Korea
基金
新加坡国家研究基金会;
关键词
D O I
10.1016/j.cplett.2004.03.152
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
We present calculations for the structures and the tautomerization reaction of purine and purine -(H2O)(n) (n = 1-3) clusters. We find two pathways (via the carbene and the sp(3)-type intermediate) for the 9 <----> 7 tautomerization of bare purine. The barrier heights for the 9 --> 3 and 9 --> 7 tautomerization of bare purine are calculated to be large (60-70 kcal/mol). Hydrogen bonding with the water molecule(s), however, dramatically lowers the 9 --> 3 barrier by the concerted multiple proton transfer mechanism, favoring the formation of the conformer 3(H)- relative to the 7(H)-purine in the microsolvated environment, in contrast to the gas phase or the aqueous solution. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:384 / 388
页数:5
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