The F•••HO intramolecular hydrogen bond forming five-membered rings hardly appear in monocyclic organofluorine compounds
The F•••HO intramolecular hydrogen bond forming five-membered rings hardly appear in monocyclic organofluorine compounds
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DOI：
10.1039/c2ra00039c
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发表时间：
2012-01-01
期刊：
影响因子：
3.9
通讯作者：
Rittner, Roberto
中科院分区：
文献类型：
--
作者：
Cormanich, Rodrigo A.;Freitas, Matheus P.;Rittner, Roberto
本文强调有机分子中的氟原子需要特殊的几何要求才能形成分子内氢键（H键）。在B3LYP/aug-cc-pVDZ理论水平上进行计算，并利用分子中原子的量子理论应用于一系列具有相似C = C(F)-C(OH)= C片段的单环化合物，预测在形成五元环时不存在F中心点HO分子内氢键。事实上，表明刚性环施加的几何限制是阻止氟参与这种F中心点HO分子内氢键的主要原因。
This paper emphasizes that fluorine atoms in organic molecules need special geometric requirements to experience intramolecular hydrogen bonds (H-bonds). Calculations at the B3LYP/aug-cc-pVDZ theoretical level and using the quantum theory of atoms in molecules applied over a series of monocyclic compounds, which have similar C = C(F)-C(OH)= C fragments, predict that the F center dot center dot center dot HO intramolecular H-bond does not exist when forming five-membered rings. Indeed, it is shown that the geometric restrictions imposed by the rigid rings are the main reasons in preventing fluorine participating in such a F center dot center dot center dot HO intramolecular H-bond.