基于量子化学的研究和对一些结构相关的喹唑啉衍生物的亲油性评估

IF 0.7 Q4 CHEMISTRY, MULTIDISCIPLINARY
Sümeyya Seri̇n
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引用次数: 0

摘要

这项工作的主要构想是从理论方面探讨取代基对一些喹唑啉衍生物(Q1-Q4)的热力学、电子和亲油特性的影响。通过计算方法评估了芳香环同碳上的甲基、乙基、氯和溴取代基引起的变化。为此,利用 B3LYP 函数和 6-311++G(d, p) 分裂价三重泽塔基集,在真空和两种不同环境(二甲基亚砜和水)下同时对甲喹酮(Q1)、依他喹酮(Q2)、甲喹酮(Q3)和甲溴喹酮(Q4)化合物进行了基于 DFT 的计算。 计算得出的热力学量表明,卤素取代更为可取。分子静电位(MEP)绘图技术直观地评估了取代基修饰对静电表面特征的影响。为了揭示 Q1-Q4 的化学反应行为,计算了基于 DFT 的反应性标识符。此外,还根据自然键轨道(NBO)理论评估了受取代影响的分子内相互作用。NBO 结果显示,π-π* 相互作用在每种化合物中都占主导地位。对上述化合物的亲脂性进行了数值和视觉评估。两种方法的数据相互支持。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Quantum Chemical-Based Investigations and Lipophilicity Evaluations on Some Structurally Related Quinazoline Derivatives
This work was chiefly conceived to explore the substituent effects on thermodynamic, electronic and lipophilic characteristics of some quinazoline derivatives (Q1-Q4) from theoretical aspects. The variations caused by methyl, ethyl, chlorine and bromine substituents on the same carbon of the aromatic ring were evaluated with a computational approach. In accordance with this purpose, simultaneously, DFT-based calculations were performed for vacuum and two different surroundings (DMSO and water) on methaqualone (Q1), etaqualone (Q2), mecloqualone (Q3), and mebroqualone (Q4) compounds by using the B3LYP functional and 6-311++G(d, p) split-valence triple zeta basis set.  The computed thermodynamic quantities revealed that the halogen substitution was more preferable. The effect of substituent modification on electrostatic surface features was evaluated visually by molecular electrostatic potential (MEP) mapping technique. To shed light on the chemical reactivity behaviors of the Q1-Q4, DFT-based reactivity identifiers were computed. Also, the intramolecular interactions affected by substitution were evaluated on the basis of the Natural Bond Orbital (NBO) theory. The NBO results revealed that π-π* interactions predominate for each compound. The lipophilic character analyzes of the mentioned compounds were evaluated both numerically and visually. The data of both methods support each other.
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来源期刊
Orbital: The Electronic Journal of Chemistry
Orbital: The Electronic Journal of Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
1.10
自引率
0.00%
发文量
25
审稿时长
10 weeks
期刊介绍: Orbital: The Electronic Journal of Chemistry is a quarterly scientific journal published by the Institute of Chemistry of the Universidade Federal de Mato Grosso do Sul, Brazil. Original contributions (in English) are welcome, which focus on all areas of Chemistry and their interfaces with Pharmacy, Biology, and Physics. Neither authors nor readers have to pay fees. The journal has an editorial team of scientists drawn from regions throughout Brazil and world, ensuring high standards for the texts published. The following categories are available for contributions: 1. Full papers 2. Reviews 3. Papers on Education 4. History of Chemistry 5. Short communications 6. Technical notes 7. Letters to the Editor The Orbital journal also publishes a number of special issues in addition to the regular ones. The central objectives of Orbital are threefold: (i) to provide the general scientific community (at regional, Brazilian, and worldwide levels) with a formal channel for the communication and dissemination of the Chemistry-related literature output by publishing original papers based on solid research and by reporting contributions which further knowledge in the field; (ii) to provide the community with open, free access to the full content of the journal, and (iii) to constitute a valuable channel for the dissemination of Chemistry-related investigations.
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