Theoretical Study of the Solvent Effect on the properties of Indole-Cation-Anion Complexes

被引:0
作者
Carrazana-Garcia, Jorge A. [1 ]
Cabaleiro-Lago, Enrique M. [1 ]
Rodriguez-Otero, Jesus [2 ]
机构
[1] Univ Santiago de Compostela, Fac Ciencias, Dept Quim Fis, Campus Lugo,Ave Alfonso X El Sabio S-N, Lugo 27002, Spain
[2] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela 15782, Spain
来源
18TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY | 2014年
关键词
solvent effect; cation-pi-anion interaction; PCM;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The properties of ternary indole-cation-anion (IMX) complexes are theoretically studied as simplified models of real systems in which some of the fragments used are parts of bigger and complicated structures, like proteins. The electro-neutrality of real systems and the presence of ions of both charges interacting simultaneously with aromatic residues in the proteins modeled justify the move from cation-pi or anion-pi (non-bonding interactions analyzed by our group in previous studies) to cation-pi-anion complexes. With the intention of approaching more the model to reality, the solvent was also included in the study: aqueous solvent was represented by a combination of PCM + explicit addition of one water molecule to some IMX complexes. As model systems for this study the complexes with indole and the following cations and anions were selected: M = Na+, NH4+; X = HCOO-, NO3- or C-l-. The effect of the solvent was studied not only on the energy but as well on some structural parameters like the proton transfer from the ammonium cation to the basic anion and the cation-anion separation. The results indicate that the PCM method alone properly reproduces the main energetic and geometrical changes, even at quantitative level, but the explicit hydration allows refining the solvent effect and detecting cases that do not follow the general trend.
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