A DFT Study on Benzotrifuroxan and its Isomers

Türker, Lemi

doi:10.1080/10406631003608479

Cited by 6 publications

(3 citation statements)

References 25 publications

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“…Computational studies are helpful to investigate the interesting and challenging chemistry exhibited by benzofuroxan and its derivatives (29)(30)(31)(32)(33)(34). One of the striking behavior of BFO is the molecular rearrangement of it which involves 1,2-dinitroso benzene intermediate (30,31).…”

Section: Introductionmentioning

confidence: 99%

Isomeric Structures of Furoxan-Fused [2,2]paracyclophane—A DFT Study

Türker

Gümüş

2012

Polycyclic Aromatic Compounds

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The present study theoretically deals with furoxan-fused [2,2]paracyclophane systems and some structures possibly involved in their isomerization processes. These intermediate structures are certain di-and tetra-nitroso derivatives and systems having dioxadiazatidine ring(s). Computationally, B3LYP/6-31G(d,p) level of density functional theory has been employed. Certain properties of the systems, such as geometries, energies, and aromaticity of the benzenoid rings, are harvested and discussed.

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Section: Introductionmentioning

confidence: 99%

Isomeric Structures of Furoxan-Fused [2,2]paracyclophane—A DFT Study

Türker

Gümüş

2012

Polycyclic Aromatic Compounds

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“…BTF was first synthesized by Turek in 1931 [3], and its synthetic route has been improved in recent years to satisfy its wide application in energetic fields [4]. BTF has attracted much attention in many areas due to its unique advantages including high energy, zero oxygen balance, and low shock sensitivity [5]. The density of BTF (1.90 g cm À 3 ) is higher than that of RDX (1.79 g cm À 3 ), and BTF shows higher detonation velocity (8277 m s À 1 ) compared to TATB (7606 m s À 1 ) [6].…”

Section: Introductionmentioning

confidence: 99%

Photo‐Induced Discoloration and the Corresponding Mechanism of Benzotrifuroxan under UV Irradiation

Chen

Zhuang

et al. 2022

Propellants Explo Pyrotec

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Benzotrifuroxan (BTF) as a powerful and hydrogen‐free explosive discolors under UV irradiation, but the process remains unclear. Herein, we comprehensively investigated the photochemical process and mechanism of BTF under UV irradiation. A pink color is observed in BTF after irradiation with 365‐nm light, while BTF becomes brown by 254‐nm light. Besides BTF, compound 1 is detected by ultrahigh‐performance liquid chromatography after UV irradiation. Compound 1 is prone to be yielded under 254‐nm irradiation compared to 365‐nm irradiation. Meanwhile, it is easier for the formation of compound 1 in BTF solution rather than solid BTF. Additionally, a small amount of compound 2 is found in BTF solution after 254‐nm irradiation over 120 min. A new photodegradation pathway of BTF is proposed through high‐resolution mass spectrometry. Compound 1 is produced as the main product through the isomerization of the N‐oxide of BTF, and BTF also loses NO to yield compound 2. Through the analysis of scanning electron microscopy, BTF exhibits different crystal structures between 365‐nm irradiation and 254‐nm irradiation. Nano holes are widely observed in solid BTF after 365‐nm irradiation, but these holes disappear under 254‐nm irradiation. Thus, the differences originating from the content of compound 1 and the crystal structure of BTF may lead to the discoloration of BTF under UV irradiation.

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“…Makhova and Fershtat, outlined recent advances in the synthesis and functionalization of 1,2,5-oxadiazole-2-oxides [2]. Some computational studies on structures having furoxan systems have been reported recently [3][4][5][6]. Some energetic compounds possessing 1,2,5-oxadiazole 2-oxide system have been reported [7].…”

Section: Introductionmentioning

confidence: 99%

3(4)-Amino-4(3)-nitro-1,2,5-oxadiazole-2-oxides and their Ring-opened Isomers-A DFT Treatment

Türker

2020

EJCS

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Amino and nitro substituted 1,2,5-oxadiazole-2-oxide isomers and their ring-opened nitroso forms have been subjected to density functional treatment at the level of B3LYP/6-311++G(d,p). The transition states for the ring opening processes are obtained and the corresponding activation energies have been calculated. Also, 1,3- and 1,5-proton tautomerism yielding imine, oxime and aci forms are investigated. For all the structures, the stabilities, the HOMO, LUMO energies and the interfrontier molecular orbital energy gaps are obtained and the effects of substituents (NH2 and NO2) are discussed.

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A DFT Study on Benzotrifuroxan and its Isomers

Cited by 6 publications

References 25 publications

Isomeric Structures of Furoxan-Fused [2,2]paracyclophane—A DFT Study

Isomeric Structures of Furoxan-Fused [2,2]paracyclophane—A DFT Study

Photo‐Induced Discoloration and the Corresponding Mechanism of Benzotrifuroxan under UV Irradiation

3(4)-Amino-4(3)-nitro-1,2,5-oxadiazole-2-oxides and their Ring-opened Isomers-A DFT Treatment

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