Irshaidat Tareq
Department of Chemistry, College of Sciences, Al-Hussein Bin Talal University, P. O. Box 20, Ma'an, Jordan.
Molecules. 2017 Apr 30;22(5):720. doi: 10.3390/molecules22050720.
Tautomerism links with many applications and remains an attracting feature in exploring novel systems. In this regard, properties of indene-based HNCCCN segments have not received any considerable attention. In this computational organic chemistry study, first, to calculate the proton transfer energy barrier at a reasonable cost, the study identified an accurate forth order Møller-Plesset perturbation theory-density functional theory (MP4-DFT) protocol equivalent to the outstanding pioneering benchmark calculations. The calculations illustrate that the two tautomers of the 4-amino-3-iminoindene nucleus are separated by a considerable energy barrier while featuring different molecular orbital characteristics; frontier orbital distribution, λmax, and energies, which are known basic requirements in molecular switching and logic circuit applications. The N-H/BH₂ substitution was found to have significant influence on the electronic structure of the skeleton. Similarities in the two tautomers and the boron derivative to properties of known molecular materials have been found.
互变异构与许多应用相关联，并且在探索新型体系方面仍然是一个具有吸引力的特性。在这方面，基于茚的HNCCCN片段的性质尚未受到太多关注。在这项计算有机化学研究中，首先，为了以合理的成本计算质子转移能垒，该研究确定了一种准确的四阶莫勒-普莱塞特微扰理论-密度泛函理论（MP4-DFT）方案，该方案等同于出色的开创性基准计算。计算结果表明，4-氨基-3-亚氨基茚核的两种互变异构体被一个相当大的能垒隔开，同时具有不同的分子轨道特征；前沿轨道分布、最大吸收波长和能量，这些是分子开关和逻辑电路应用中已知的基本要求。发现N-H/BH₂取代对骨架的电子结构有显著影响。已发现这两种互变异构体以及硼衍生物与已知分子材料的性质存在相似之处。
