Interaction of (S)-thalidomide molecule with four nucleobases: adenine, guanine, cytosine and thymine, is investigated in details employing density functional theory methods. Different mutual positions of the molecules are considered, with the starting geometries enabling hydrogen bond interactions between the monomers. Optimization of geometrical parameters is carried out within the B3LYP/6-311G** approximation and followed by evaluation of vibrational frequencies. Binding and interaction energies are calculated employing exchange-correlation functionals including long-range corrections and properly diffuse basis sets. The strongest interaction exists within the (S)-thalidomide–guanine complex. Interestingly, in one of the investigated (S)-thalidomide–guanine complexes two bifurcated hydrogen bonds are observed. The two hydrogens involved in one of them are bonded to a carbon atom in the α position relative to carbonyl group. The present study can be useful in the design of new anticancer and antiviral drugs interacting selectively with DNA or RNA.

（S）-沙利度胺分子与四个核碱基：腺嘌呤，鸟嘌呤，胞嘧啶和胸腺嘧啶的相互作用，采用密度泛函理论方法进行了详细研究。考虑了分子的不同相互位置，起始几何形状使得单体之间能够发生氢键相互作用。在B3LYP / 6-311G **近似值内进行几何参数的优化，然后评估振动频率。使用包括长距离校正和适当扩散基集在内的交换相关函数计算结合能和相互作用能。（S）-沙利度胺-鸟嘌呤复合物中存在最强的相互作用。有趣的是，在所研究的一个（小号）-沙利度胺-鸟嘌呤配合物观察到两个分叉的氢键。其中一个涉及的两个氢键合在相对于羰基的α位的碳原子上。本研究可用于设计与DNA或RNA选择性相互作用的新抗癌和抗病毒药物。