Hydrogen-Bonded Tetramers of Carbamazepine
Hydrogen-Bonded Tetramers of Carbamazepine
复制标题
DOI：
10.1021/acs.jpcc.9b11466
复制
发表时间：
2020-02
影响因子：
3.7
通讯作者：
Angela M. Silski-Devlin;Jacob P. Petersen;Jonathan Liu;Gwendylan Turner;J. Poutsma;S. Kandel
中科院分区：
文献类型：
--
作者：
Angela M. Silski-Devlin;Jacob P. Petersen;Jonathan Liu;Gwendylan Turner;J. Poutsma;S. Kandel
在这项研究中，药物卡马西平和相关分子二苯并氮杂卓制备在Au（111）表面和可视化使用扫描隧道显微镜。卡马西平的单层导致高度有序的四聚体簇，而其中酰胺基团被去除的分子类似物二苯并氮杂卓的单层由无序簇组成。卡马西平的电喷雾电离质谱（ESI-MS）显示出一个相对较强的四聚体峰，其强度约为三聚体峰的6倍，表明4分子簇的异常稳定性。二苯并氮杂卓的质谱显示出相对较少的聚集，并且没有显示出对四聚体的偏好。我们的分子模拟表明，卡马西平四聚体是一个NH-O氢键簇，与相邻分子的苯环之间的增强π-π相互作用是负责的长程有序的四聚体。
In this study, the pharmaceutical carbamazepine and the related molecule dibenzazepine are prepared on the Au(111) surface and visualized using scanning tunneling microscopy. Monolayers of carbamazepine result in tetrameric clusters that are highly ordered, while a monolayer of the molecular analog in which the amide group is removed, dibenzazepine, consists of disordered clustering. Electrospray ionization mass spectra (ESI-MS) of carbamazepine shows a relatively intense tetramer peak that is roughly 6 times more intense than the trimer peak, indicating the anomalous stability of a 4-molecule cluster. A mass spectrum of dibenzazepine shows relatively little clustering and does not show preference for tetramers. Our molecular modeling suggests that the carbamazepine tetramer is a NH-O hydrogen-bonded cluster, with reinforcing π-π interactions between benzene rings of neighboring molecules that are responsible for the long-range order of the tetramers.