Solid-State NMR-Assisted Dynamic Characterization of two Isostructural Solvates of 5α-Bromo-6β,19-Epoxy-Androstan-3β,17β-Diol Diacetate

利用固态核磁共振技术对5α-溴-6β,19-环氧-雄甾烷-3β,17β-二醇二乙酸酯的两种同构溶剂化物进行动态表征

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Abstract

The study reports on the rotational dynamics of acetone-d(6) (Form II) and DMSO-d(6) (Form III) within the crystalline structures of two solvates of 5α-bromo-6β,19-epoxy-androstan-3β,17β-diol diacetate (Compound 1) by means of solid-state Nuclear Magnetic Resonance through the quadrupolar (2)H spin-echo technique. The spectral data allowed the determination of the activation barriers (E(a)) for rotation of the solvent molecules, with 6.24 kcal mol(-1) for deuterated acetone in the Form II-d(6) and 8.19 kcal mol(-1) for the case of deuterated dimethylsulfoxide in Form III-d(6). The use of calculations and the Transition State theory through the linear Eyring equation suggested that although the acetone molecules experience a low activation energy (E(a) = 6.24 kcal mol(-1)), a highly ordered transition state during the molecular motion reduces its rotational rate. Conversely, the DMSO molecules, with a higher activation barrier (E(a) = 8.19 kcal mol(-1)) attributed to a denser packing coefficient, have faster motional rates. Based on complementary X-ray and NMR spectroscopy techniques, this work provides detailed insights into the mechanistic phenomena involved in the mobility of small molecules inside crystalline arrangements.

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