Circuit resonance energy: a key quantity that links energetic and magnetic criteria of aromaticity

Journal of the American Chemical Society
Jun-ichi Aihara

Abstract

Energetic and magnetic criteria of aromaticity are different in nature and sometimes make different predictions as to the aromaticity of a polycyclic pi-system. Thus, some charged polycyclic pi-systems are aromatic but paratropic. We derived the individual circuit contributions to aromaticity from the magnetic response of a polycyclic pi-system and named them circuit resonance energies (CREs). Each CRE has the same sign and essentially the same magnitude as the corresponding cyclic conjugation energy (CCE) defined by Bosanac and Gutman. Such CREs were found to play a crucial role in associating the energetic criteria for determining the degree of aromaticity with the magnetic ones. We can now interpret both energetic and magnetic criteria of aromaticity consistently in terms of CREs. Ring-current diamagnetism proved to be the tendency of a cyclic pi-system to retain aromatic stabilization energy (ASE) at the level of individual circuits.

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Citations

May 9, 2009·Journal of Molecular Modeling·Jun-ichi Aihara, Masakazu Makino
May 30, 2013·Journal of Molecular Modeling·Kalbinur NajmidinTursungul Tawar
May 21, 2011·The Journal of Physical Chemistry. a·Rika SekineJun-ichi Aihara
Jul 14, 2011·The Journal of Physical Chemistry. a·Jun-ichi AiharaToshimasa Ishida
Aug 16, 2012·The Journal of Physical Chemistry. a·Guglielmo Monaco, Riccardo Zanasi
Jul 10, 2012·The Journal of Physical Chemistry. a·Masakazu Makino, Jun-ichi Aihara
Oct 31, 2012·The Journal of Physical Chemistry. a·Jun-ichi AiharaMasakazu Makino
May 17, 2013·The Journal of Physical Chemistry. a·Jun-ichi AiharaJerry R Dias
Sep 14, 2013·The Journal of Physical Chemistry. a·Jun-ichi AiharaKenkichi Sakamoto
May 1, 2008·Physical Chemistry Chemical Physics : PCCP·Snehadrinarayan KhatuaPratim K Chattaraj
Dec 22, 2009·Physical Chemistry Chemical Physics : PCCP·Arkadiusz CiesielskiJun-ichi Aihara
Apr 8, 2010·Physical Chemistry Chemical Physics : PCCP·Remi ChauvinJean-Paul Malrieu
Oct 1, 2011·Physical Chemistry Chemical Physics : PCCP·Milan RandićDejan Plavšić
Oct 14, 2014·The Journal of Physical Chemistry. a·Jerry Ray Dias
Aug 7, 2009·The Journal of Chemical Physics·Guglielmo Monaco, Riccardo Zanasi
Aug 25, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ankita Puri, Raakhi Gupta
Apr 25, 2017·Journal of Computational Chemistry·Dariusz W SzczepanikHalina Szatylowicz
Jul 21, 2017·Physical Chemistry Chemical Physics : PCCP·Maria DimitrovaDage Sundholm
Feb 16, 2016·Physical Chemistry Chemical Physics : PCCP·Jun-Ichi Aihara
Jan 24, 2014·Angewandte Chemie·Sébastien BlanchardMax Malacria
Sep 5, 2006·Chemistry : a European Journal·Patrick BultinckRobert Ponec
Oct 27, 2006·Journal of Computational Chemistry·Patrick BultinckRamon Carbó-Dorca
Oct 26, 2006·Journal of Computational Chemistry·Marcos MandadoRicardo A Mosquera
Feb 1, 2007·Chemistry : a European Journal·Michał K CyrańskiLeonardus W Jenneskens
Mar 8, 2007·Journal of Computational Chemistry·Marcos MandadoRicardo A Mosquera
Feb 14, 2008·Journal of Computational Chemistry·Ferran FeixasMiquel Solà
Jan 31, 2008·Chemistry : a European Journal·Stijn FiasPatrick Bultinck
Nov 20, 2008·Chemistry : a European Journal·Ilaria CiofiniPhilippe P Lainé
Jul 11, 2009·Organic & Biomolecular Chemistry·Jun-ichi Aihara, Hideki Horibe
May 2, 2009·Journal of Computational Chemistry·J Oscar C Jiménez-HallaMiquel Solà
Jul 29, 2009·Journal of Computational Chemistry·Mercedes Alonso, Bernardo Herradón
Feb 18, 2011·Chemistry : a European Journal·Nicolás OteroMarcos Mandado
Dec 22, 2009·Organic & Biomolecular Chemistry·Jun-Ichi Aihara, Masakazu Makino
Feb 2, 2010·Physical Chemistry Chemical Physics : PCCP·Mercedes Alonso, Bernardo Herradón
Jun 14, 2012·Organic & Biomolecular Chemistry·Yuto NakagamiJun-ichi Aihara
Jul 10, 2019·Journal of Computational Chemistry·José E Barquera-Lozada
Jan 19, 2008·Chemistry, an Asian Journal·Jun-Ichi Aihara, Masakazu Makino
Jul 22, 2015·Journal of Computational Chemistry·Nicolás OteroPanaghiotis Karamanis
May 28, 2019·Physical Chemistry Chemical Physics : PCCP·Guglielmo Monaco, Riccardo Zanasi
Feb 27, 2007·Chemistry : a European Journal·Mercedes Alonso, Bernardo Herradón
Jul 19, 2012·Chemistry : a European Journal·Mercedes AlonsoFrank de Proft
Apr 11, 2017·Frontiers in Chemistry·Miquel Solà
May 4, 2018·Journal of Molecular Modeling·Ablimit AbdukadirLutpulla Hushur
Sep 3, 2020·Royal Society Open Science·Maimaitijiang Tuersun, Ablikim Kerim

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