About the Aromaticity of symm-Triaminotrinitrobenzene

The Journal of Physical Chemistry. a
Iryna V OmelchenkoZdzisław Latajka

Abstract

Aromaticity and structural features of the isolated symm-triaminotrinitrobenzene (TATB) were examined using the nonempirical ab initio quantum chemical method and molecular dynamics at the Car-Parrinello level. Different criteria of the aromaticity were combined with the study of conformational flexibility of molecule and analysis of the electron density distribution. It was found that the cooperative effect of the resonance-assisted hydrogen bonds results in the ultimate decreasing aromaticity of the benzene ring in TATB. Values of the HOMA index indicate that it could be classified as low-aromatic in equilibrium state at zero temperature but completely nonaromatic at room temperature. An extremely high flexibility of the molecule is also not typical for aromatic rings. The electron delocalization in H-bonded O═N-C═C-N-H quasi-aromatic rings was found to be greater than that in the benzene ring of TATB.

References

Jan 15, 1991·Physical Review. B, Condensed Matter·N Troullier, J L Martins
Nov 25, 1985·Physical Review Letters·R Car, M Parrinello
Oct 28, 1996·Physical Review Letters·J P PerdewM Ernzerhof
Nov 17, 2001·Chemical Reviews·T M Krygowski, M K Cyrański
May 13, 2004·Chemical Reviews·Alexandru T BalabanAlan R Katritzky
Oct 13, 2005·Chemical Reviews·Lucjan SobczykTadeusz Marek Krygowski
Oct 13, 2005·Chemical Reviews·Zhongfang ChenPaul von Ragué Schleyer
Feb 7, 2007·The Journal of Physical Chemistry. a·Gang Zhang, Charles B Musgrave
Jul 11, 2008·The Journal of Physical Chemistry. a·Svetlana V ShishkinaJerzy Leszczynski
Jun 10, 2010·Physical Chemistry Chemical Physics : PCCP·Al'ona FurmanchukJerzy Leszczynski
Jun 18, 2010·Journal of Hazardous Materials·Veera M BodduR Damavarapu
Jun 26, 2010·The Journal of Organic Chemistry·Tadeusz M KrygowskiMarcin Palusiak
Nov 11, 2011·The Journal of Chemical Physics·Alistair J DavidsonChoong-Shik Yoo
Dec 2, 2011·The Journal of Physical Chemistry. a·Aneta Jezierska-MazzarelloTadeusz Marek Krygowski
May 25, 2012·The Journal of Physical Chemistry. a·Irena Majerz, Teresa Dziembowska
Nov 28, 2012·Journal of Molecular Modeling·Oleg V ShishkinJerzy Leszczynski
Jan 17, 2013·Physical Chemistry Chemical Physics : PCCP·Robert W GóraSławomir J Grabowski
Jan 3, 2014·Angewandte Chemie·Colin R Groom, Frank H Allen
Sep 13, 2014·Journal of the American Chemical Society·Judy I WuPaul von Ragué Schleyer
Dec 23, 2014·The Journal of Physical Chemistry. a·María P Romero-FernándezJuan C Palacios
Jul 21, 2016·Physical Chemistry Chemical Physics : PCCP·José Manuel Guevara-VelaTomás Rocha-Rinza

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