On the aromatic stabilization of corannulene and coronene

Literature Information

Publication Date 2011-09-15
DOI 10.1039/C1CP21994D
Impact Factor 3.676
Authors

Michał A. Dobrowolski, Michał K. Cyrański


View Original

Abstract

The application of set of homodesmotic reactions allowed us to estimate the aromatic stabilization energy (ASE) of corannulene and coronene. Appropriate reactions have been applied to balance syn/anti mismatches in di-, tetra- and hexamethylene substituted derivatives. Based on many different polycyclic reference structures that compensate the effect of strain in the corannulene moiety the value of ASE comes to 44.5 kcal mol−1. Planar corannulene is more stabilized by cyclic π-electron delocalization by ca. 10.7 kcal mol−1, as compared with a bowl-shaped system. A similar approach for coronene leads to an ASE equal to 58.4 kcal mol−1.

Related Literature

Palladium-catalyzed enantioselective [5 + 4] annulation of ortho-quinone methides and vinylethylene carbonates

Chao Xia, Dong-Chao Wang, Gui-Rong Qu

2020-05-08 Research Article

DOI: 10.1039/D0QO00128G

Contents list

Front/Back Matter

DOI: 10.1039/C9OB90024A

Back cover

Cover

DOI: 10.1039/D0QO90026E

Construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation utilizing a ferrocene derived bifunctional phosphine catalyst

Wenjun Luo, Bingxuan Shao, Jingyi Li, Xiao Xiao, Dingguo Song, Fei Ling, Weihui Zhong

2020-03-19 Research Article

DOI: 10.1039/D0QO00140F

Radical SAM-dependent adenosylation catalyzed by l-tyrosine lyases

Yujie Wu, Runze Wu, Dhanaraju Mandalapu, Xinjian Ji, Tuo Chen, Wei Ding, Qi Zhang

2018-12-06 Communication

DOI: 10.1039/C8OB02906G

Posttranscriptional spin labeling of RNA by tetrazine-based cycloaddition

Christof Domnick, Gregor Hagelueken, Frank Eggert, Olav Schiemann, Stephanie Kath-Schorr

2018-11-28 Communication

DOI: 10.1039/C8OB02597E

An Aspidosperma-type alkaloid dimer from Tabernaemontana bovina as a candidate for the inhibition of microglial activation

Si-Meng Zhao, Mei-Fen Bao, Xiang-Hai Cai

2020-04-27 Research Article

DOI: 10.1039/D0QO00296H

Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles

Luyao Li, Bo Zhu, Huihui Fan, Zhiyong Jiang, Junbiao Chang

2020-04-17 Research Article

DOI: 10.1039/D0QO00348D

Applications of N′-monofunctionalised TsDPEN derivatives in asymmetric catalysis

Jonathan Barrios-Rivera, Yingjian Xu, Martin Wills

2019-01-04 Review Article

DOI: 10.1039/C8OB02889C

You might also like

Compound Q&A

What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?

(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...

16326-97-9(1R,3S)-1,3-Cyclopen...
Compound Q&A

What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?

When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...

637-31-0N'-[4-(Dimethylamino...
Compound Q&A

Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?

There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...

1352318-16-15-(2,4-Difluoropheny...
Compound Q&A

What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?

1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...

382141-68-61-(3-Methoxyphenoxy)...
Compound Q&A

Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?

Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...

18660-81-6Tetrodotoxin Citrate
Compound Q&A

What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?

2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...

225641-84-92-Methyl-2-propanyl ...
Compound Q&A

How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?

Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...

16261-80-64-(2-Hydroxyhexafluo...
Compound Q&A

How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?

2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...

102507-19-72-Methyl-2-propanyl ...
Compound Q&A

What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?

Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...

20735-15-3Benzeneethanamine, α...
Compound Q&A

Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?

In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...

20691-84-33-{(E)-[4-(Dimethyla...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.