Experimental and theoretical study of N¹-hexylcytosine and N¹-hexylcytosinium nitrate: the crucial role of hydrophobic and anion-¦Ð interactions

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• 作者：Miquel Barcel¨®-Oliver ; Antonio Bauz¨¢ ; Beatriz A. Baquero ; Angel Garc¨ªa-Raso ; Angel Terr¨®n ; Elies Molins ; Antonio Frontera
• 关键词：Cytosine ; Anion&ndash ; ¦Ð interaction ; DFT calculations ; Hydrophobic interaction ; Nitrate
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：25 September, 2013
• 年：2013
• 卷：54
• 期：39
• 页码：5355-5360
• 全文大小：1498 K

文摘

We report the synthesis and X-ray characterization of N¹-hexylcytosine (1) and N¹-hexylcytosinium nitrate (2). N¹-hexylcytosine (1) does not follow the same behaviour previously described for N¹-hexylthymine and N¹-hexyluracil in the solid state. This different behavior has been analyzed by means of density functional theory (DFT) calculations including the latest available correction for dispersion (D3). In addition hydrophobic and anion-¦Ð noncovalent interactions play a key role in stabilizing the 3D architectures of the compounds, which have been energetically studied using theoretical calculations and compared with similar structures retrieved from the Cambridge Structural Database (CSD). The anion-¦Ð-anion binding mode observed for nitrate in compound 2 is also observed in several crystal structures involving cytosine ring coordinated to transition metals.