The ten chemically transparent dinitronaphthalene isomers and their radical anions

Date

2010-01-01

Author

Bozkaya, Ugur
Schaefer, Henry F.

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

129
views

0
downloads

Dinitroaromatics have a long scientific history, with very recent (e.g. S.F. Nelsen, M.N. Weaver and J.P. Telo, J. Phys. Chem. A 113, 7730 (2009)) important contributions. The electron affinities for the nitrobenzene, dinitrobenzene and dinitronaphthalene isomers are predicted. The ten obvious structures of neutral dinitronaphthalene (DNN) have been predicted from theory. These ten isomers span an energetic range of 14 kcal mol-1, with the global minimum 2,7 structure lying only 0.3 kcal mol-1 below 2,6. The analogous ten isomers of the DNN radical anion have also been optimized and display a broader range of 25 kcal mol-1. Among the anions 2,6-DNN lies below the next most favourable isomer (2,7) by 6.5 kcal mol-1. The three known adiabatic electron affinities are predicted to be 1.12 (nitrobenzene), 1.91 (ortho-dinitrobenzene), 1.94 (meta-dinitrobenzene), and 2.32 eV (para-dinitrobenzene), values that range from 0.12 to 0.32 eV above the most recent experiments. We conclude that the experimental vertical detachment energy (VDE) of 3.10 eV for para-dinitrobenzene is too high by a surprising 0.85 eV. For the dinitronaphthalenes the following adiabatic electron affinities are estimated; 1.70 (1,2-dinitronaphtalene), 1.81 (1,3), 2.12 (1,4), 1.85 (1,5), 1.78 (1,6), 1.86 (1,7), 1.47 (1,8), 1.53 (2,3), 1.99 (2,6), and 1.69 eV (2,7).

Subject Keywords

Physical and Theoretical Chemistry, Biophysics, Molecular Biology, Condensed Matter Physics

URI

https://hdl.handle.net/11511/65698

DOI

https://doi.org/10.1080/00268976.2010.507225

Collections

Department of Chemistry, Conference / Seminar

Suggestions

OpenMETU
Core

The ortho- to meta- isomerization of dicarba-closo-dodecaborane Türker, Burhan Lemi (Elsevier BV, 2003-08-01) By means of AMI(RHF) type semiempirical quantum chemical calculations, the conversion of ortho- dicarba-closododecaborane to its meta- isomer is throughly investigated by considering two intermediate structures previously proposed.
The stabilities of N-Cl bonds in biocidal materials Akdağ, Akın; McKee, Michael L.; Worley, S. D. (American Chemical Society (ACS), 2006-05-01) N-halamine chemistry has been a research topic of considerable importance in these laboratories for over two decades. N-halamine compounds are useful in preparing biocidal materials. There are three N-Cl moieties available in cyclic N-halamine compounds: imide, amide, and amine. The stabilities toward the release of free halogen have been experimentally shown to decrease in the order amine > amide > imide. In this work, this generalization has been tested theoretically at the level of B3LYP/6-31+G(d) and us...
The valence electronic structure and conformational flexibility of epichlorohydrin Stranges, S.; Alagia, M.; Decleva, P.; Stener, M.; Fronzoni, G.; Toffolı, Danıele; Speranza, M.; Catone, D.; Turchini, S.; Prosperi, T.; Zema, N.; Contini, G.; Keheyan, Y. (Royal Society of Chemistry (RSC), 2011-01-01) The electronic structure of epichlorohydrin is investigated in the whole valence region by a combined experimental and theoretical study. The issue of controversial assignments of the molecular electronic structure is here addressed. Photoelectron spectra (PES) and Threshold Photoelectron spectra (TPES) of room temperature molecules in the gas phase are recorded. Geometries and energies of the stable conformers due to internal rotation of the C-C-C-Cl dihedral angle, gauche-II (g-II), gauche-I (g-I), and ci...
Physicochemical mechanisms of different biopolymers' (lysozyme, gum arabic, whey protein, chitosan) adsorption on green tea extract loaded liposomes Dag, Damla; Güner, Selen; Öztop, Halil Mecit (Elsevier BV, 2019-10-01) Having various domains of applicability, liposomes have been the issue of many studies since 1960s. Kinetically stable nature of liposomes required incorporation of other substituents to gain storage stability and interaction of liposomes with polymers, electrolytes, proteins or lipids still requires further investigation to explain the underlying mechanism. In this study, polyphenol-rich green tea extract was encapsulated into liposomes by means of microfluidization in two different aqueous media (pH = 3.8...
The role of antiferromagnetic exchange interactions in dinuclear Cr(III) dithiocarbamates and a stepwise behavior of magnetic moment AYTEKİN, ÖZLEM; Bayri, A. (Pleiades Publishing Ltd, 2012-12-01) In this study the role of the antiferromagnetic interactions in recently synthesized dinuclear Cr(III) complex has been investigated. Since there was not enough structural information for the characterization of the synthesis, we claim that there should be antiferromagnetic interactions between the dinuclear Fe(III) ions, if the proposed structure is the real structure. A new experiment is proposed to test the predictions of this theoretical investigation.

Citation Formats

U. Bozkaya and H. F. Schaefer, “The ten chemically transparent dinitronaphthalene isomers and their radical anions,” 2010, vol. 108, p. 2491, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/65698.