Literature DB >> 11700102

The acenes: is there a relationship between aromatic stabilization and reactivity?

P von Ragué Schleyer1, M Manoharan, H Jiao, F Stahl.   

Abstract

[reaction--see text] Despite the increasing reactivity from benzene to heptacene, the acene resonance energies per pi electron are nearly constant. The reactivities (computed activation energies) of the individual acene rings correlate with the reaction energies and depend on the product stabilities. Nucleus-independent chemical shifts (NICS; note the sizes of the red dots, above) indicate that the more reactive inner rings actually are more aromatic than the less reactive outer rings and even more aromatic than benzene itself.

Entities:  

Year:  2001        PMID: 11700102     DOI: 10.1021/ol016553b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  14 in total

1.  Ab initio molecular orbital and density functional studies on the ring-opening reaction of oxetene.

Authors:  S Jayaprakash; Jebakumar Jeevanandam; K Subramani
Journal:  J Mol Model       Date:  2014-11-05       Impact factor: 1.810

2.  DFT study of 1-butyl-3-methylimidazolium salicylate: a third-generation ionic liquid.

Authors:  Stevan Armaković; Sanja J Armaković; Milan Vraneš; Aleksandar Tot; Slobodan Gadžurić
Journal:  J Mol Model       Date:  2015-08-30       Impact factor: 1.810

3.  First-Principles Prediction of Enthalpies of Formation for Polycyclic Aromatic Hydrocarbons and Derivatives.

Authors:  Thomas C Allison; Donald R Burgess
Journal:  J Phys Chem A       Date:  2015-11-09       Impact factor: 2.781

4.  Oxidative Coupling with Zr(IV) Supported by a Noninnocent Anthracene-Based Ligand: Application to the Catalytic Cotrimerization of Alkynes and Nitriles to Pyrimidines.

Authors:  Choon Heng Low; Jeffrey N Rosenberg; Marco A Lopez; Theodor Agapie
Journal:  J Am Chem Soc       Date:  2018-09-14       Impact factor: 15.419

5.  The Generation and Reactions of Quinone Methides.

Authors:  Maria M Toteva; John P Richard
Journal:  Adv Phys Org Chem       Date:  2011-01-01       Impact factor: 2.833

6.  Non-bonding interactions and non-covalent delocalization effects play a critical role in the relative stability of group 12 complexes arising from interaction of diethanoldithiocarbamate with the cations of transition metals Zn(II), Cd(II), and Hg(II): a theoretical study.

Authors:  Homayoon Bahrami; Saeed Farhadi; Firouzeh Siadatnasab
Journal:  J Mol Model       Date:  2016-06-14       Impact factor: 1.810

7.  On-Surface Hydrogen-Induced Covalent Coupling of Polycyclic Aromatic Hydrocarbons via a Superhydrogenated Intermediate.

Authors:  Carlos Sánchez-Sánchez; José Ignacio Martínez; Nerea Ruiz Del Arbol; Pascal Ruffieux; Roman Fasel; María Francisca López; Pedro L de Andres; José Ángel Martín-Gago
Journal:  J Am Chem Soc       Date:  2019-01-29       Impact factor: 15.419

Review 8.  Forty years of Clar's aromatic π-sextet rule.

Authors:  Miquel Solà
Journal:  Front Chem       Date:  2013-10-17       Impact factor: 5.221

9.  cAAC-Stabilized 9,10-diboraanthracenes-Acenes with Open-Shell Singlet Biradical Ground States.

Authors:  Christian Saalfrank; Felipe Fantuzzi; Thomas Kupfer; Benedikt Ritschel; Kai Hammond; Ivo Krummenacher; Rüdiger Bertermann; Raphael Wirthensohn; Maik Finze; Paul Schmid; Volker Engel; Bernd Engels; Holger Braunschweig
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-25       Impact factor: 15.336

10.  Core-level spectra and molecular deformation in adsorption: V-shaped pentacene on Al(001).

Authors:  Anu Baby; He Lin; Gian Paolo Brivio; Luca Floreano; Guido Fratesi
Journal:  Beilstein J Nanotechnol       Date:  2015-11-27       Impact factor: 3.649

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