The predictive power of aromaticity: quantitative correlation between aromaticity and ionization potentials and HOMO-LUMO gaps in oligomers of benzene, pyrrole, furan, and thiophene

Physical Chemistry Chemical Physics : PCCP
Renana Gershoni-PoranneAmnon Stanger

Abstract

Aromaticity is a central and ubiquitous concept in organic chemistry, and is used extensively to explain various phenomena. Yet, aromaticity cannot be observed or measured as a property in its own right and, to date, only qualitative and semi-quantitative relationships have been described between aromaticity and an observable property. We now demonstrate for the first time a robust quantitative relationship between the HOMO-LUMO gap and adiabatic ionization potential of a polycyclic aromatic hydrocarbon oligomer - both measurable physical quantities - and its aromaticity, as quantified by the Nucleus Independent Chemical Shift (NICS) index. The agreement found for a range of structurally and electronically diverse oligomeric systems of varying lengths is so well-behaved as to enable accurate prediction of the properties of longer members of the respective oligomer family. The established correlation allows for preliminary screening of compounds geared towards functional use.

References

Nov 17, 2001·Chemical Reviews·R H Mitchell
Nov 17, 2001·Chemical Reviews·J A Gomes, R B Mallion
Nov 17, 2001·Chemical Reviews·T M Krygowski, M K Cyrański
Nov 17, 2001·Chemical Reviews·F De Proft, P Geerlings
Dec 26, 2001·Chemical Reviews·D T McQuadeT M Swager
Feb 16, 2002·The Journal of Organic Chemistry·Michal K CyrañskiPaul von Ragué Schleyer
Sep 15, 2004·Magnetic Resonance in Chemistry : MRC·P W FowlerL W Jenneskens
Jan 11, 2005·The Journal of Chemical Physics·Eduard MatitoMiquel Solà
Oct 13, 2005·Chemical Reviews·Miklos KerteszShujiang Yang
Oct 13, 2005·Chemical Reviews·Zhongfang ChenPaul von Ragué Schleyer
Feb 24, 2006·Organic Letters·Hossein Fallah-Bagher-ShaidaeiPaul v R Schleyer
Nov 3, 2006·Organic Letters·Sanjio S Zade, Michael Bendikov
Feb 7, 2007·The Journal of Physical Chemistry. a·Gang Zhang, Charles B Musgrave
Jun 23, 2007·The Journal of Physical Chemistry. a·Jerzy CioslowskiMiquel Solà
Apr 1, 2009·Chemical Communications : Chem Comm·Amnon Stanger
Feb 4, 2010·Journal of the American Chemical Society·Ori GidronMichael Bendikov
Mar 4, 2010·The Journal of Organic Chemistry·Amnon Stanger
Oct 15, 2010·Accounts of Chemical Research·Sanjio S ZadeMichael Bendikov
Dec 18, 2010·Chemical Communications : Chem Comm·Ori GidronDmitrii F Perepichka
Sep 13, 2011·Physical Chemistry Chemical Physics : PCCP·Heike FlieglDage Sundholm
Sep 29, 2011·Physical Chemistry Chemical Physics : PCCP·Alexandru T Balaban
Oct 16, 2012·Angewandte Chemie·Bharat KumarBenjamin T King
Jan 9, 2014·Journal of the American Chemical Society·Wenbo ChenRonald Breslow
Jan 29, 2014·Angewandte Chemie·Ori Gidron, Michael Bendikov
Mar 20, 2014·ACS Applied Materials & Interfaces·Lei ZhangAlejandro L Briseno
Mar 29, 2014·Chemistry : a European Journal·Renana Gershoni-Poranne, Amnon Stanger
Aug 22, 2014·Physical Chemistry Chemical Physics : PCCP·Dariusz W SzczepanikJanusz Mrozek
Apr 11, 2015·Chemical Society Reviews·Ferran FeixasMiquel Solà
Jun 3, 2015·Chemical Society Reviews·Renana Gershoni-Poranne, Amnon Stanger
Feb 16, 2016·Physical Chemistry Chemical Physics : PCCP·Eduard Matito
Sep 17, 2016·The Journal of Organic Chemistry·Dani SetiawanDieter Cremer
Apr 11, 2017·Frontiers in Chemistry·Miquel Solà
Jul 3, 1996·Journal of the American Chemical Society·Paul von Ragué SchleyerNicolaas J R van Eikema Hommes
Jan 1, 2015·Chemical Science·Dennis SheberlaMichael Bendikov
Jan 2, 2018·Journal of the American Chemical Society·Thijs StuyverMercedes Alonso
Jan 1, 2015·Chemtexts·T M Krygowski, H Szatylowicz

❮ Previous
Next ❯

Citations

Feb 12, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Patrick Finkelstein, Renana Gershoni-Poranne
May 14, 2019·Angewandte Chemie·Sérgio R DomingosMelanie Schnell
Oct 28, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Amnon StangerRiccardo Zanasi
Aug 14, 2020·Angewandte Chemie·Qingdong ZhengJinyun Wang
Jun 10, 2019·The Journal of Chemical Physics·Soumyadeb DeyHenry F Schaefer
Jan 16, 2021·The Journal of Chemical Physics·Eno PaenurkRenana Gershoni-Poranne
Jun 8, 2021·Chemical Science·Marco BragatoO Anatole von Lilienfeld
Mar 3, 2020·The Journal of Physical Chemistry. a·Raghavendra VenkatramanVenkatesan Subramanian
Dec 12, 2020·The Journal of Physical Chemistry. a·Sajith M VijayanDavita L Watkins
Oct 29, 2021·Organic & Biomolecular Chemistry·Zhili WenJudy I-Chia Wu

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR

Software Mentioned

FP
MS Excel
NICS
Scan
Aroma
Gaussian

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.