Due to the high symmetry and low polarity of the cyclopropane (C₃H₆), cyclobutane (C₄H₈), prismane (C₆H₆), and cubane (C₈H₈), it is widely known that these structures unlikely act as proton receptors to form intermolecular interactions with monoprotic acids, such as the hydrogen fluoride. Although the C₃H₆···HF, C₄H₈···HF, C₆H₆···HF, and C₈H₈···HF are weakly bound complexes, in this current work, all of them were definitively certified on the basis of a theoretical analysis. In according with the structural parameters and spectroscopy modes appraised through the density‐functional theory calculations, the more accentuated perturbations are manifested in the hydrogen fluoride. The new hydrogen bond forms framed as pseudo‐π···H and C···H were unveiled through the calculations of the quantum theory of atoms in molecules and natural bond orbital. In this context, the knowledge about the nature of these hydrogen bonds is necessary, wherein it used the symmetry‐adapted perturbation theory for computing the contributions of the electrostatic, polarization, exchange, dispersion, and charge transfer terms. Lastly, the practical behavior of these hydrocarbons under the condition to form intermolecular interactions was examined by taking into account the solvent effect with calculations of the polarizable continuum model.

中文翻译：

---

在环状和立方非极性烃上形成罕见的拟π···HF和C···HF氢键的最终挑战

由于环丙烷（C ₃ H ₆），环丁烷（C ₄ H ₈），棱烷（C ₆ H ₆）和古巴（C ₈ H ₈）的高对称性和低极性，众所周知，这些结构不太可能充当质子受体与单质子酸（如氟化氢）形成分子间相互作用。C ₃ H ₆ ···HF，C ₄ H ₈ ···HF，C ₆ H ₆ ···HF，C ₈ H ₈···HF是弱结合的络合物，在当前的工作中，所有这些都在理论分析的基础上得到了明确的证明。根据通过密度泛函理论计算得出的结构参数和光谱模式，氟化氢中出现了更为突出的扰动。通过计算分子中原子的原子理论和自然键轨道，揭示了新的氢键形式，分别为伪π··H和C··H。在这种情况下，有关这些氢键性质的知识是必要的，其中它使用了适应对称性的扰动理论来计算静电，极化，交换，色散和电荷转移项的贡献。最后，