Verde Andrés, López Juan Carlos, Blanco Susana
Departamento de Química Física y Química Inorgánica, Facultad de Ciencias, IU CINQUIMA, Universidad de Valladolid, 47011 Valladolid, Spain.
Int J Mol Sci. 2025 Jun 17;26(12):5806. doi: 10.3390/ijms26125806.
Sotolon is a chiral furanone derivative featuring three distinct oxygen atoms at carbonyl, hydroxyl, and cyclic ether groups that can serve as hydrogen-bond acceptor sites, making it an ideal model system for probing water's preferential interactions with competing functional groups. In this study, the rotational spectrum of sotolon and its microsolvated complexes, representing the early stages of hydration, was investigated using chirped-pulse Fourier transform microwave (CP-FTMW) spectroscopy. The conformational landscape of sotolon is dominated by a single conformer stabilized by an intramolecular O-H···O=C hydrogen bond. During hydration, water molecules disrupt this interaction by forming closed hydrogen-bonded cycles, resulting in mono- and dihydrated complexes. High-level theoretical calculations underscore the central role of electrostatic interactions in stabilizing these hydrated structures. Furthermore, / splittings observed in the rotational spectrum, arising from the internal rotation of one of sotolon's methyl groups, provide insight into how hydration modulates the methyl internal rotation barrier.
sotolon是一种手性呋喃酮衍生物，在羰基、羟基和环醚基团处具有三个不同的氧原子，这些氧原子可作为氢键受体位点，使其成为探究水与竞争性官能团优先相互作用的理想模型体系。在本研究中，使用啁啾脉冲傅里叶变换微波（CP-FTMW）光谱研究了sotolon及其微溶剂化配合物的转动光谱，这些配合物代表了水合作用的早期阶段。sotolon的构象态势由通过分子内O-H···O=C氢键稳定的单一构象体主导。在水合过程中，水分子通过形成封闭的氢键环破坏这种相互作用，从而产生单水合和二水合配合物。高水平的理论计算强调了静电相互作用在稳定这些水合结构中的核心作用。此外，sotolon的一个甲基的内旋转在转动光谱中观察到的 / 分裂，为水合作用如何调节甲基内旋转势垒提供了见解。
