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多环芳烃和杂环芳烃化合物的生成焓

Enthalpy of Formation of Polycyclic Aromatic Hydrocarbons and Heterocyclic Aromatic Compounds.

作者信息

Çilesiz Umut, Sincer Eren Yaşar, Dedeoglu Burcu, Aviyente Viktorya

机构信息

Department of Chemistry, Bogazici University, Bebek, Istanbul 34342 , Türkiye.

Department of Chemistry, Gebze Technical University, Gebze, Kocaeli 41400, Türkiye.

出版信息

ACS Omega. 2025 May 28;10(22):23433-23439. doi: 10.1021/acsomega.5c01887. eCollection 2025 Jun 10.

DOI:10.1021/acsomega.5c01887
PMID:40521528
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12163763/
Abstract

The standard enthalpy of formation is an important indicator of the heat involved in a chemical reaction. In this work, benchmark calculations with quasi-isodesmic type reactions have been performed on 8 different polycyclic aromatic hydrocarbons (PAHs) with 9 different methodologies. All geometry optimizations were carried out at the B2PLYP-D3, B3LYP-D3, CAM-B3LYP-D3, LC-WPBE-D3, M05-2X-D3, M06-2X-D3, WB97XD, DSDPBEP86, and PBE0DH levels in conjunction with the cc-pVTZ basis set. The DSDPBEP86-optimized isodesmic reactions yield remarkably good agreement with the experimental data for most of the compounds. For the heterocyclic aromatic compounds, quasi-isodesmic reactions are carried out successfully using the cost-effective B2PLYP-D3/cc-pVTZ and B3LYP-D3/cc-pVTZ methodologies. In the case of alkyl-substituted thiophene derivatives, quasi-isodesmic reactions and the connectivity-based hierarchy (CBH) methods have yielded enthalpies of formation close to those from experiments with B2PLYP-D3/cc-pVTZ.

摘要

标准生成焓是化学反应中所涉及热量的一个重要指标。在本研究中，采用9种不同方法对8种不同的多环芳烃（PAH）进行了准等键型反应的基准计算。所有几何结构优化均在B2PLYP-D3、B3LYP-D3、CAM-B3LYP-D3、LC-WPBE-D3、M05-2X-D3、M06-2X-D3、WB97XD、DSDPBEP86和PBE0DH水平下结合cc-pVTZ基组进行。DSDPBEP86优化的等键反应与大多数化合物的实验数据显示出非常好的一致性。对于杂环芳烃化合物，使用经济高效的B2PLYP-D3/cc-pVTZ和B3LYP-D3/cc-pVTZ方法成功进行了准等键反应。对于烷基取代的噻吩衍生物，准等键反应和基于连接性的层次（CBH）方法得到的生成焓与B2PLYP-D3/cc-pVTZ实验值相近。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6a2/12163763/9713f0d919bc/ao5c01887_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6a2/12163763/e65c3c8d9ecb/ao5c01887_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6a2/12163763/f00fa2f10fa1/ao5c01887_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6a2/12163763/31217dc1173b/ao5c01887_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6a2/12163763/9713f0d919bc/ao5c01887_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6a2/12163763/e65c3c8d9ecb/ao5c01887_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6a2/12163763/f00fa2f10fa1/ao5c01887_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6a2/12163763/31217dc1173b/ao5c01887_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6a2/12163763/9713f0d919bc/ao5c01887_0004.jpg

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RSC Adv. 2021 Sep 6;11(47):29690-29701. doi: 10.1039/d1ra05391d. eCollection 2021 Sep 1.
3
Polycyclic aromatic hydrocarbons: from small molecules through nano-sized species towards bulk graphene.
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4
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5
How reliable is DFT in predicting relative energies of polycyclic aromatic hydrocarbon isomers? comparison of functionals from different rungs of jacob's ladder.DFT 在预测多环芳烃异构体的相对能量时有多可靠？雅各布天梯不同梯级的泛函比较。
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