Hydroxynitrobenzodifuroxan and its salts

Sitzmann, Michael E.; Bichay, Magdy; Fronabarger, John W.; Williams, M. D.; Sanborn, William B.; Gilardi, Richard

doi:10.1002/jhet.5570420613

Cited by 14 publications

(7 citation statements)

References 5 publications

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“…We further add that Scilabra et al [28] have only recently reviewed the importance of the chalcogen bond in crystalline solids, wherein it was briefly speculated that the oxygen atom can nevertheless elicit electrophilicity and hence could form close contacts with nucleophiles. In particular, it was suggested that the crystal of ( S , S )-(−)-2-methylsulfonyl-3-(2-chloro-5-nitrophenyl)oxaziridine [87] is driven by the Cl⋯O chalcogen bond and the crystal of Guanidinium 5-nitro(1,2,5)oxadiazolo(3,4-e)(2,1,3)benzoxadiazole-4-olate3,8-dioxide [88] is driven by the O⋯O chalcogen bond. While Scilabra et al [28] have stressed the presence of O-centered chalcogen bonding in both the crystal systems, such a view might be misleading, since the anion moiety in the latter crystal is stabilized by the guanidinium cation.…”

Section: Discussionmentioning

confidence: 99%

Does Oxygen Feature Chalcogen Bonding?

Varadwaj

2019

Molecules

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Using the second-order Møller–Plesset perturbation theory (MP2), together with Dunning’s all-electron correlation consistent basis set aug-cc-pVTZ, we show that the covalently bound oxygen atom present in a series of 21 prototypical monomer molecules examined does conceive a positive (or a negative) σ-hole. A σ-hole, in general, is an electron density-deficient region on a bound atom M along the outer extension of the R–M covalent bond, where R is the reminder part of the molecule, and M is the main group atom covalently bonded to R. We have also examined some exemplar 1:1 binary complexes that are formed between five randomly chosen monomers of the above series and the nitrogen- and oxygen-containing Lewis bases in N2, PN, NH3, and OH2. We show that the O-centered positive σ-hole in the selected monomers has the ability to form the chalcogen bonding interaction, and this is when the σ-hole on O is placed in the close proximity of the negative site in the partner molecule. Although the interaction energy and the various other 12 characteristics revealed from this study indicate the presence of any weakly bound interaction between the monomers in the six complexes, our result is strongly inconsistent with the general view that oxygen does not form a chalcogen-bonded interaction.

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Section: Discussionmentioning

confidence: 99%

Does Oxygen Feature Chalcogen Bonding?

Varadwaj

2019

Molecules

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“…Very specific bonding patterns can nevertheless elicit oxygen electrophilicity and close contacts with nucleophiles can be found in certain solid systems , (Figure ). In O(CN) 2 , S(CN) 2 , and Se(CN) 2 , two σ-holes are present on chalcogen atoms opposite to the cyano groups, and the respective electrostatic potentials are 31.0, 42.7, and 46.9 kcal·mol –1 .…”

Section: General Features Of Chbsmentioning

confidence: 99%

The Chalcogen Bond in Crystalline Solids: A World Parallel to Halogen Bond

2019

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Conspectus The distribution of the electron density around covalently bonded atoms is anisotropic, and this determines the presence, on atoms surface, of areas of higher and lower electron density where the electrostatic potential is frequently negative and positive, respectively. The ability of positive areas on atoms to form attractive interactions with electron rich sites became recently the subject of a flurry of papers. The halogen bond (HaB), the attractive interaction formed by halogens with nucleophiles, emerged as a quite common and dependable tool for controlling phenomena as diverse as the binding of small molecules to proteinaceous targets or the organization of molecular functional materials. The mindset developed in relation to the halogen bond prompted the interest in the tendency of elements of groups 13–16 of the periodic table to form analogous attractive interactions with nucleophiles. This Account addresses the chalcogen bond (ChB), the attractive interaction formed by group 16 elements with nucleophiles, by adopting a crystallographic point of view. Structures of organic derivatives are considered where chalcogen atoms form close contacts with nucleophiles in the geometry typical for chalcogen bonds. It is shown how sulfur, selenium, and tellurium can all form chalcogen bonds, the tendency to give rise to close contacts with nucleophiles increasing with the polarizability of the element. Also oxygen, when conveniently substituted, can form ChBs in crystalline solids. Chalcogen bonds can be strong enough to allow for the interaction to function as an effective and robust tool in crystal engineering. It is presented how chalcogen containing heteroaromatics, sulfides, disulfides, and selenium and tellurium analogues as well as some other molecular moieties can afford dependable chalcogen bond based supramolecular synthons. Particular attention is given to chalcogen containing azoles and their derivatives due to the relevance of these moieties in biosystems and molecular materials. It is shown how the interaction pattern around electrophilic chalcogen atoms frequently recalls the pattern around analogous halogen, pnictogen, and tetrel derivatives. For instance, directionalities of chalcogen bonds around sulfur and selenium in some thiazolium and selenazolium derivatives are similar to directionalities of halogen bonds around bromine and iodine in bromonium and iodonium compounds. This gives experimental evidence that similarities in the anisotropic distribution of the electron density in covalently bonded atoms translates in similarities in their recognition and self-assembly behavior. For instance, the analogies in interaction patterns of carbonitrile substituted elements of groups 17, 16, 15, and 14 will be presented. While the extensive experimental and theoretical data available in the literature prove that HaB and ChB form twin supramolecular synthons in the solid, more experimental information has to become available before such a statement can be safely extended to interactions wherein ele...

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“…Benzofuroxan derivatives have attracted considerable attention due to their high density, good oxygen balance, good detonation performance, and excellent thermal stability. − 7-Amino-6-nitrobenzodifuroxan (ANBDF) is an outstanding representative of the benzofuroxan derivatives. − ANBDF has comparable detonation performance with 1,3,5-trinitro-1,3,5-triazinane (RDX), one famous explosive, but does higher density (1.93 g/cm 3 ) and better thermal stability (decomposes around 200 °C) than RDX. The special approximately planar molecule structure with one amino group, one nitro group, and two furoxan rings on the benzene ring and the formation of the intermolecular hydrogen bond between the amino moiety and nitro group make ANBDF possess favorable mechanical sensitivity.…”

Section: Introductionmentioning

confidence: 99%

Structural Transformations and Absorption Properties of Crystalline 7-Amino-6-nitrobenzodifuroxan under High Pressures

Zhu

Xiao

2013

J. Phys. Chem. C

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The structural, electronic, and absorption properties of crystalline 7-amino-6-nitrobenzodifuroxan (ANBDF) under hydrostatic compression of 0–110 GPa have been studied by using DFT calculations. Our results show that there three structural transformations occurred at the pressure of 35, 70, and 100 GPa. The first structural transformation makes the positions of the molecules in the crystal rearranged and obviously improves the planarity. The second one forms a new C7–O10 covalent bond and transforms a boat conformation. The last one takes place with the rupture of the C7–O10 bond, forming another new C8–O10 covalent bond and transforming of a boat conformation to a chair. An analysis of the band gap and density of states of ANBDF indicates that its electronic character transforms into a metallic system at 70 GPa, and it becomes more sensitive under compression. The absorption spectra show that ANBDF has relatively high optical activity with the increasing pressure, and the structural transformations that occurred at 70 and 100 GPa can broaden its absorption region in the energy range of below 2 eV and above 20 eV, respectively. This work may provide useful information in understanding how ANBDF behaves under high pressures.

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Hydroxynitrobenzodifuroxan and its salts

Cited by 14 publications

References 5 publications

Does Oxygen Feature Chalcogen Bonding?

Does Oxygen Feature Chalcogen Bonding?

The Chalcogen Bond in Crystalline Solids: A World Parallel to Halogen Bond

Structural Transformations and Absorption Properties of Crystalline 7-Amino-6-nitrobenzodifuroxan under High Pressures

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