Benito Mónica, Frontera Antonio, Molins Elies
Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus UAB, 08193 Bellaterra, Spain.
Departament de Química, Universitat de les Illes Balears, Ctra. Valldemosa km 7.5, E-07122 Palma de Mallorca, Spain.
Cryst Growth Des. 2023 Mar 8;23(4):2932-2940. doi: 10.1021/acs.cgd.3c00067. eCollection 2023 Apr 5.
The application of halogen bonding in pharmaceutical chemistry remains a challenge. In this work, novel halogen-bonded cocrystals based on azole antifungal active pharmaceutical ingredients (APIs) and the ditopic molecule 1,4-diiodotetrafluorobenzene are reported. Their crystal structural features, spectroscopic properties, and thermal stability were studied. The components are bound through I···N from the triazole moieties present in all of the compounds. The molecular electrostatic potential (MEP) surfaces and quantum theory of atoms in molecules (QTAIM) calculations are used to rationalize the presence of hydrogen and halogen bonds in the resulting structures and their energetic analysis. The relative halogen bond ability of the different groups of voriconazole, fluconazole, and itraconazole was analyzed using MEP surfaces, demonstrating this approach to be an interesting tool to predict halogen-bonding preferences.
卤素键在药物化学中的应用仍然是一个挑战。在这项工作中，报道了基于唑类抗真菌活性药物成分（API）和双位点分子1,4-二碘四氟苯的新型卤素键合共晶体。研究了它们的晶体结构特征、光谱性质和热稳定性。所有化合物中的三唑部分通过I···N键合各组分。利用分子静电势（MEP）表面和分子中的原子量子理论（QTAIM）计算来合理化所得结构中氢键和卤素键的存在及其能量分析。使用MEP表面分析了伏立康唑、氟康唑和伊曲康唑不同基团的相对卤素键能力，证明这种方法是预测卤素键偏好的一个有趣工具。
