Why are some polycyclic aromatic hydrocarbons extremely reactive?

Literature Information

Publication Date
DOI 10.1039/A902032B
Impact Factor 3.676
Authors


View Original

Abstract

Higher members of the polyacene series are extremely reactive although they are aromatic in nature. This aspect of aromatic chemistry can be explained using conventional indices of kinetic stability, such as a localization energy and a HOMO–LUMO energy separation. Large polyacene molecules have smaller localization energies and smaller HOMO–LUMO energy separations than their respective polyene references defined using matching polynomials. These molecules are presumed to be thermodynamically more stable but kinetically less stable than non-aromatic polyolefins. The same situation is sometimes observed in other groups of polycyclic aromatic hydrocarbons (PAHs). Such highly reactive PAH molecules were found to be substructures of metallic one-dimensional benzenoid polymers.

Related Literature

Beta zeolite supported on silicon carbide for Friedel–Crafts fixed-bed reactions

Gauthier Winé, Joseph Matta, Jean-Philippe Tessonnier, Cuong Pham-Huu, Marc-Jacques Ledoux

2003-01-16 Communication

DOI: 10.1039/B209858J

Anionic triazacyclononanes: new supporting ligands in main group and transition metal organometallic chemistry

Joseph A. R. Schmidt, Garth R. Giesbrecht, Chunming Cui, John Arnold

2002-11-28 Feature Article

DOI: 10.1039/B208525A

TEM stereo-imaging of mesoporous zeolite single crystals

Iver Schmidt, Anna Carlsson, Søren Dahl, Michael Brorson, Claus J. H. Jacobsen

2003-03-14 Communication

DOI: 10.1039/B212646J

Site-selective RNA scission at two sites for precise genotyping of SNPs by mass spectrometry‡

Akinori Kuzuya, Ryo Mizoguchi, Fumi Morisawa, Makoto Komiyama

2003-02-25 Communication

DOI: 10.1039/B300368J

Formation and destruction of the guanine quartet in solution observed by cold-spray ionization mass spectrometry

Shigeru Sakamoto, Isao Saito

2003-02-17 Communication

DOI: 10.1039/B212432G

Construction of extended networks with a trimeric pyrazole synthon

Ishtvan Boldog, Eduard B. Rusanov, Joachim Sieler, Steffen Blaurock, Konstantin V. Domasevitch

2003-02-25 Communication

DOI: 10.1039/B212540D

Identification of novel sulfur-containing derivatives of chlorophyll a in a Recent sediment

Angela H. Squier, Dominic A. Hodgson, Brendan J. Keely

2003-02-10 Communication

DOI: 10.1039/B212243J

Polyoxometalate-catalysed epoxidation of 1-octene with hydrogen peroxide in microemulsions coupled with ultrafiltration

Arnold Lambert, Pawel Plucinski, Ivan V. Kozhevnikov

2003-02-17 Communication

DOI: 10.1039/B300494P

The first example of direct oxidation of sulfides to sulfones by an osmate molecular oxygen system

Boyapati M. Choudary, Chinta Reddy V. Reddy, Billakanti V. Prakash, Mannepalli L. Kantam, B. Sreedhar

2003-02-20 Communication

DOI: 10.1039/B212749K

You might also like

Compound Q&A

What precautions should be taken when handling 4-(2-Furylmethyl)thiomorpholine 1,1-dioxide (CAS: 79206-94-3)?

When handling 4-(2-Furylmethyl)thiomorpholine 1,1-dioxide (CAS: 79206-94-3), it ...

79206-94-34-(2-Furylmethyl)thi...
Compound Q&A

What precautions should be taken when handling 4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide (CAS: 71320-77-9)?

When handling 4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide (CAS: 71320-77-9), it...

71320-77-94-Chloro-N-[2-(4-mor...
Compound Q&A

How should waste containing 2-[2-(2-Methoxyethoxy)ethoxy]ethyl 4-methylbenzenesulfonate (CAS: 62921-74-8) be handled?

Waste containing this compound (CAS: 62921-74-8) should be handled according to ...

62921-74-82-[2-(2-Methoxyethox...
Compound Q&A

How should waste containing (S)-Methyl 2-amino-3-cyclohexylpropanoate be handled?

Waste containing (S)-Methyl 2-amino-3-cyclohexylpropanoate should be collected i...

40056-18-6(S)-Methyl 2-amino-3...
166882-70-85-({4-[(2S,4R)-4-Hyd...
Compound Q&A

Are there alternatives to (2E)-3-(3,4-Dichlorophenyl)acrylic acid (CAS: 7312-27-8) in synthesis?

There are several alternatives to (2E)-3-(3,4-Dichlorophenyl)acrylic acid in syn...

7312-27-8(2E)-3-(3,4-Dichloro...
Compound Q&A

How should Ethyl 6-(2-nitrophenyl)imidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 925437-84-9) be stored?

Ethyl 6-(2-nitrophenyl)imidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 925437-84...

925437-84-9Ethyl 6-(2-nitrophen...
Compound Q&A

How should waste containing 2-(1,3-Thiazol-2-yl)ethanamine (CAS: 18453-07-1) be handled?

Waste containing 2-(1,3-Thiazol-2-yl)ethanamine (CAS: 18453-07-1) should be coll...

18453-07-12-(1,3-Thiazol-2-yl)...
Compound Q&A

How is Methyl 5-iodo-2-methylbenzoate (CAS: 103440-54-6) typically synthesized?

Methyl 5-iodo-2-methylbenzoate can be synthesized through the iodination of meth...

103440-54-6Methyl 5-iodo-2-meth...
Compound Q&A

How is 5-Chloro[1,2,4]triazolo[1,5-a]pyridine (CAS: 1427399-34-5) typically synthesized?

5-Chloro[1,2,4]triazolo[1,5-a]pyridine is commonly synthesized via the condensat...

1427399-34-55-Chloro[1,2,4]triaz...

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.