A comparative study of X-ray structural analysis, DFT computations, and Hirshfeld surface analysis for decahydroacridine-1,8-diones

IF 2.2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of the Iranian Chemical Society Pub Date : 2024-06-04 DOI:10.1007/s13738-024-03045-3
Fatemeh S. Hosseininasab, Hamid R. Memarian, Hadi Amiri Rudbari, Olivier Blacque
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Abstract

Crystal structure analysis and DFT computational calculation of two symmetrical and unsymmetrical decahydroacridine-1,8-diones (DHACs) were carried out to elucidate the effect of the aryl-substituted heterocyclic core in these compounds on the comparative bond lengths, bond, and dihedral angles. According to these findings, the central heterocyclic ring in these compounds is exhibited in the pseudo-boat conformation, in which the aryl substitution occupies the pseudo-axial position. Moreover, the fused outer rings were in the twisted half-chair conformation. The weak and strong inter- and intramolecular interactions between the suitable donor–acceptor positions (N‒H···O, C‒H···O, H‒N···H and C‒H···π of the C=C double bond) in symmetrical and enantiomeric pairs of unsymmetrical DHACs affect the orientation of the molecules in the crystal packing. The relative contributions of various intermolecular interactions in these compounds are evaluated using Hirshfeld surface analysis. The DFT calculations were performed to outline the optimized structure, molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs), natural bond orbital (NBO) and to elucidate the effect of the space orientation of the attached aryl ring toward the heterocyclic ring on the total energy content of DHAC 2. Additionally, MEP analysis in DHAC 2 revealed that the negative electrostatic potential is more concentrated around the O1-atom of the C1=O1 double bond than the O2-atom of the C13=O2 double bond. The results of the NBO analysis demonstrated that in the crystal packing of compounds 1 and 2 the strongest intermolecular interaction occurs from the LP(2)O2 to σ*(N1–H) and LP(1)O1 to σ*(N1‒H), respectively.

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十氢吖啶-1,8-二酮的 X 射线结构分析、DFT 计算和 Hirshfeld 表面分析比较研究
对两种对称和不对称的十氢吖啶-1,8-二酮(DHACs)进行了晶体结构分析和 DFT 计算,以阐明这些化合物中芳基取代的杂环核心对比较键长、键角和二面角的影响。根据这些发现,这些化合物中的中心杂环呈假舟构象,其中芳基取代占据假轴位置。此外,融合的外环呈扭曲的半对椅构象。对称和非对称 DHAC 对映体中合适的供体-受体位置(C=C 双键的 N-H--O、C-H--O、H-N-H 和 C-H--π)之间的分子间和分子内弱相互作用会影响分子在晶体堆积中的取向。利用 Hirshfeld 表面分析评估了这些化合物中各种分子间相互作用的相对贡献。通过 DFT 计算勾勒出了 DHAC 2 的优化结构、分子静电位 (MEP)、前沿分子轨道 (FMO)、天然键轨道 (NBO),并阐明了附着芳基环朝向杂环的空间取向对 DHAC 2 总能量含量的影响。此外,DHAC 2 的 MEP 分析表明,负静电势更集中在 C1=O1 双键的 O1 原子周围,而不是 C13=O2 双键的 O2 原子周围。NBO 分析结果表明,在化合物 1 和 2 的晶体结构中,最强的分子间相互作用分别发生在 LP(2)O2 到 σ*(N1-H) 和 LP(1)O1 到 σ*(N1-H)之间。
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来源期刊
CiteScore
4.40
自引率
8.30%
发文量
230
审稿时长
5.6 months
期刊介绍: JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.
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