Institute of Chemistry, University of Silesia in Katowice, Szkolna 9, 40-006, Katowice, Poland.
J Mol Model. 2020 Feb 8;26(3):53. doi: 10.1007/s00894-019-4266-2.
In this work, the geometry, acid-base properties, pK, electronic spectra, and fluorescence spectrum of anticonvulsant drug lamotrigine (LTG) are investigated with the DFT/TD-DFT method and PCM solvent model. Calculated transition with the B3LYP functional at 295 nm corresponds to experimental absorption transition at 306 nm in water. In acidic conditions, the computed maximum transition occurs at 249 nm, comparing with experimental one at 270 nm. The dependence of calculated transitions on density functional used and different solvents in PCM model was studied. The computed transition of fluorescence is at 435 nm, while experimental occurs at 370 nm. Maps of electrostatic potential (MEPs) for S and S reveal that the ground state of LTG is more polar than the first excited state. Structurally, in the excited state of LTG, the triazine ring is noticeably distorted. Graphical Abstract Molecular elecrostatic potentials for S and S states of the lamotrigine molecule.
本工作采用 DFT/TD-DFT 方法和 PCM 溶剂模型研究了抗惊厥药物拉莫三嗪（LTG）的几何形状、酸碱性质、pK、电子光谱和荧光光谱。用 B3LYP 函数在 295nm 处计算的跃迁与水中 306nm 的实验吸收跃迁相对应。在酸性条件下，计算出的最大跃迁出现在 249nm，而实验值出现在 270nm。研究了不同密度泛函和 PCM 模型中不同溶剂对计算跃迁的影响。计算出的荧光跃迁位于 435nm，而实验值出现在 370nm。静电势（MEPs）图对于 S 和 S 揭示了 LTG 的基态比第一激发态更具极性。结构上，在 LTG 的激发态中，三嗪环明显变形。
