Description of heteroaromaticity on the basis of π-electron density anisotropy

Literature Information

Publication Date 2014-04-25
DOI 10.1039/C4CP01125B
Impact Factor 3.676
Authors

Rohoullah Firouzi, Sahar Sharifi Ardani


View Original

Abstract

It is demonstrated that there is a direct connection between aromaticity and the anisotropy of the π-electron density on planes parallel to the molecular ring. The electron density anisotropy on the plane is measured through the ratio of the in-plane Hessian eigenvalues associated with the eigenvectors lying in the plane. Computations on a wide-ranging set of well-characterized monocyclic systems containing heteroatoms validate the correlation between this one-electron density-based descriptor and aromaticity; in aromatic compounds, the in-plane Hessian eigenvalues are degenerate (or near degenerate) and the anisotropy of the π-electron density is undirected, whereas the results for antiaromatic rings are reversed and the degeneracy of the eigenvalues completely disappears. This finding is in line with our very recent study on [n]annulenes and provides further evidence that the anisotropy of the π-electron density should be considered as a new manifestation of aromaticity.

Related Literature

Isolation and characterisation of the mixed-metal alkyl amide [(TMEDA)Na(μ-Bu)(μ-TMP)Mg(TMP)], an unexpected chelate-trapped intermediate in the formation of inverse crowns

Eva Hevia, Daniel J. Gallagher, Alan R. Kennedy, Robert E. Mulvey, Charles T. O'Hara, Christine Talmard

2004-09-23 Communication

DOI: 10.1039/B410293B

A C3-symmetric molecular scaffold for the construction of large receptors

Gebhard Haberhauer, Thomas Oeser, Frank Rominger

2004-08-06 Communication

DOI: 10.1039/B406335J

Mechanism of hydrogen transfer to imines from a hydroxycyclopentadienyl ruthenium hydride. Support for a stepwise mechanism

Joseph S. M. Samec, Alida H. Éll, Jan-E. Bäckvall

2004-10-06 Communication

DOI: 10.1039/B410698A

Donor–acceptor nanoensembles of soluble carbon nanotubes

G. N. A. Rahman, Jeff Ramey, Massimo Marcaccio, Demis Paolucci, Francesco Paolucci, Shuhui Qin, Warren T. Ford, Domenico Balbinot, Norbert Jux, Nikos Tagmatarchis, Maurizio Prato

2004-08-10 Communication

DOI: 10.1039/B406933A

Synthesis and characterization of electron-rich nickel tris-carbene complexes‡

Xile Hu, Ingrid Castro-Rodriguez, Karsten Meyer

2004-08-23 Communication

DOI: 10.1039/B409241D

Design of a robust Ru(salen) complex: aziridination with improved turnover number using N-arylsulfonyl azides as precursors

Kazufumi Omura, Tatsuya Uchida, Ryo Irie, Tsutomu Katsuki

2004-08-13 Communication

DOI: 10.1039/B407693A

First lanthanide dipolar complexes for second-order nonlinear optics

Katell Sénéchal, Loïc Toupet, Isabelle Ledoux, Joseph Zyss, Hubert Le Bozec, Olivier Maury

2004-09-08 Communication

DOI: 10.1039/B407073A

Nanoporosity of an interpenetrated NbO-type molecular framework studied by single crystal X-ray diffraction

Prasad V. Ganesan, Cameron J. Kepert

2004-09-01 Communication

DOI: 10.1039/B409543J

You might also like

Compound Q&A

What are the main uses of (3alpha,5alpha)-3-Hydroxypregnane-11,20-dione (CAS: 23930-19-0)?

(3alpha,5alpha)-3-Hydroxypregnane-11,20-dione is primarily used in the pharmaceu...

23930-19-0(3alpha,5alpha)-3-Hy...
Compound Q&A

What is the market or research trend for 4-Amino-6-chloro-2-pyridinecarboxylic acid (CAS: 546141-56-4)?

The market for 4-Amino-6-chloro-2-pyridinecarboxylic acid (CAS: 546141-56-4) is ...

546141-56-44-Amino-6-chloro-2-p...
Compound Q&A

Are there alternatives to (2-Benzoylethyl)trimethylammonium chloride (CAS: 24472-88-6) in synthesis?

Alternatives to (2-Benzoylethyl)trimethylammonium chloride (CAS: 24472-88-6) in ...

24472-88-6(2-Benzoylethyl)trim...
Compound Q&A

Is N-[4-Nitro-3-(trifluoromethyl)phenyl]acetamide (CAS: 393-12-4) safe?

N-[4-Nitro-3-(trifluoromethyl)phenyl]acetamide (CAS: 393-12-4) is generally safe...

393-12-4N-[4-Nitro-3-(triflu...
Compound Q&A

Are there alternatives to N,N'-Bis(3-aminopropyl)-1,3-propanediamine (CAS: 4605-14-5) in synthesis?

There are alternatives to N,N'-Bis(3-aminopropyl)-1,3-propanediamine (CAS: 4605-...

4605-14-5N,N'-Bis(3-aminoprop...
Compound Q&A

What precautions should be taken when handling Aluminium trihexadecanoate (CAS: 555-35-1)?

When handling Aluminium trihexadecanoate, it is important to use appropriate per...

555-35-1Aluminium trihexadec...
Compound Q&A

What is (1,1-Dioxido-3-oxo-1,2-benzothiazol-2(3H)-yl)acetic acid (CAS: 52188-11-1)?

(1,1-Dioxido-3-oxo-1,2-benzothiazol-2(3H)-yl)acetic acid is a chemical compound ...

52188-11-1(1,1-Dioxido-3-oxo-1...
Compound Q&A

Are there alternatives to 5,5-dimethyloxolan-2-one (CAS: 3123-97-5) in synthesis?

Several alternatives to 5,5-dimethyloxolan-2-one (CAS: 3123-97-5) can be used in...

3123-97-55,5-dimethyloxolan-2...

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.