Literature DB >> 24638823

Aromaticity in transition structures.

Paul von Ragué Schleyer1, Judy I Wu, Fernando P Cossío, Israel Fernández.   

Abstract

Aromaticity is an essential concept in chemistry, employed to account for the unusual stability, reactivity, molecular structures, and other properties of many unsaturated organic compounds. This concept was later extended to inorganic molecules and to saturated systems with mobile electrons, as well as to transition structures, the focus of the present review. Although transition structures are inherently delocalized, not all exhibit aromaticity. We contrast here examples of pericyclic reaction transition structures (where aromaticity is significant) with those for illustrative pseudo-pericyclic reactions (where aromaticity is less or not important). Non-pericyclic reactions may also have aromatic transition structures. State-of-the-art computational methods to evaluate the aromaticity of transition structures are described briefly.

Year:  2014        PMID: 24638823     DOI: 10.1039/c4cs00012a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  11 in total

1.  Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazoles via novel 6π-electrocyclizations of 3-azahepta trienyl cations.

Authors:  Sovan Sundar Giri; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

2.  Photoinduced Changes in Aromaticity Facilitate Electrocyclization of Dithienylbenzene Switches.

Authors:  Baswanth Oruganti; Péter Pál Kalapos; Varada Bhargav; Gábor London; Bo Durbeej
Journal:  J Am Chem Soc       Date:  2020-07-28       Impact factor: 15.419

3.  Coarctate and Möbius: The Helical Orbitals of Allene and Other Cumulenes.

Authors:  Marc H Garner; Roald Hoffmann; Sten Rettrup; Gemma C Solomon
Journal:  ACS Cent Sci       Date:  2018-04-25       Impact factor: 14.553

4.  Revisiting the Rearrangement of Dewar Thiophenes.

Authors:  Sara Gómez; Edison Osorio; Eugenia Dzib; Rafael Islas; Albeiro Restrepo; Gabriel Merino
Journal:  Molecules       Date:  2020-01-10       Impact factor: 4.411

5.  Reactions of 1,2,4-Oxadiazole[4,5-a]piridinium Salts with Alcohols: the Synthesis of Alkoxybutadienyl 1,2,4-Oxadiazoles.

Authors:  Mattia Moiola; Marco Leusciatti; Paolo Quadrelli
Journal:  ChemistryOpen       Date:  2020-02-03       Impact factor: 2.911

6.  Bonding, Aromaticity and Isomerization of Furfuraldehyde through Off-Nucleus Isotropic Magnetic Shielding.

Authors:  Muntadar A H Al-Yassiri
Journal:  ChemistryOpen       Date:  2021-10       Impact factor: 2.630

7.  Isoxazolium N-ylides and 1-oxa-5-azahexa-1,3,5-trienes on the way from isoxazoles to 2H-1,3-oxazines.

Authors:  Alexander F Khlebnikov; Mikhail S Novikov; Yelizaveta G Gorbunova; Ekaterina E Galenko; Kirill I Mikhailov; Viktoriia V Pakalnis; Margarita S Avdontceva
Journal:  Beilstein J Org Chem       Date:  2014-08-14       Impact factor: 2.883

8.  An isolable catenane consisting of two Möbius conjugated nanohoops.

Authors:  Yang-Yang Fan; Dandan Chen; Ze-Ao Huang; Jun Zhu; Chen-Ho Tung; Li-Zhu Wu; Huan Cong
Journal:  Nat Commun       Date:  2018-08-02       Impact factor: 14.919

9.  Electrocyclic Ring-Opening of 1,2,4-Oxadiazole[4,5-a]piridinium Chloride: a New Route to 1,2,4-Oxadiazole Dienamino Compounds.

Authors:  Stefano Carella; Misal Giuseppe Memeo; Paolo Quadrelli
Journal:  ChemistryOpen       Date:  2019-09-12       Impact factor: 2.911

10.  Hyperconjugative aromaticity and protodeauration reactivity of polyaurated indoliums.

Authors:  Kui Xiao; Yu Zhao; Jun Zhu; Liang Zhao
Journal:  Nat Commun       Date:  2019-12-10       Impact factor: 14.919

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