Density functional theory study of piperidine and diazocine compounds

Fan, Xinjian; Ju, Xue‐Hai; Xiao, Heming

doi:10.1016/j.jhazmat.2007.12.024

Cited by 48 publications

(12 citation statements)

References 27 publications

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“…The increased accumulation of electronic charge between triple-bonded carbons is an indication of enhanced chemical bonding, which means that the triple bond is very stable. Interestingly this is in contrast to previous studies on similar molecules [14][15][16][17][18][19][20] . Also it is clear that for all studied molecules a strong σ-type bonding appears between the carbon and the hydrogen atoms inside cyclohexane/piperidine ring (pink areas between ring carbons and hydrogens), while the overall ring has strong depletion of charge (purple areas around ring).…”

Section: Structure (Bond Lengths and Angles)contrasting

confidence: 99%

“…16,17 DFT calculations of piperidine compounds have also been performed to determine the heat of formation. 18 An earlier investigation has convincingly demonstrated the high accuracy and agreement between DFT methods and experimental results for 4-methylpiperidine. 19 This gives confidence that these methods are suitable for further studies of this group of compounds.…”

Section: Introductionmentioning

confidence: 84%

“…[14][15][16][17][18][19][20] Common to all these studies is that the triple bond has been found to have high reactivity. Also there is strong interest in studying the chemical reactivity of these novel materials being used as catalysts.…”

Section: Introductionmentioning

confidence: 99%

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Experimental and density functional theory studies of the novel piperidine-containing acetylene glycols

Mirsakiyeva¹,

Botkina²,

Elgammal³

et al. 2016

Arkivoc

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Synthesis routes of novel piperidine-containing acetylenes are presented. The new molecules are expected to exhibit plant growth stimulation properties. In particular, the yield in a situation of drought is expected to increase. Our synthesis makes use of the Favorskii reaction between cyclohexanone/piperidone and triple-bond containing alcohols. The structures of the obtained molecules were determined using nuclear magnetic resonance (NMR). The electronic structure and geometries of the molecules were studied theoretically using first-principles calculations based on density functional theory. The calculated geometries agree very well with the experimentally determined ones, and also allow us to determine bond lengths, angles and charge distributions inside the molecules.

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Section: Structure (Bond Lengths and Angles)contrasting

confidence: 99%

Section: Introductionmentioning

confidence: 84%

See 1 more Smart Citation

Experimental and density functional theory studies of the novel piperidine-containing acetylene glycols

Mirsakiyeva¹,

Botkina²,

Elgammal³

et al. 2016

Arkivoc

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“…Different studies illustrate that C-NO 2 is the possible trigger bond in the nitro-aromatic compounds [60,61] and it can be ruptured easily during Table 2. The BDEs for the tetrazole derivatives found to be higher than 230 kJ/mol.…”

Section: Bond Dissociation Energymentioning

confidence: 99%

Computational studies on tetrazole derivatives as potential high energy materials

2011

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The tetrazole is an important functionality of the most of energetic materials due to 80% nitrogen content, stability, and high enthalpy of formation. The present structure-property relationship study focuses on the optimized geometries of tetrazole derivatives obtained from density functional theory (DFT) calculations at B3LYP/6-31G* levels. The heat of formation (HOF) of tetrazole derivatives have been calculated by designing the appropriate isodesmic reactions. The increase in nitro groups on azole rings shows the remarkable increase in HOF. Density has been predicted by using CVFF force field. Increase in the nitro group increases the density. Detonation properties of the designed compounds were evaluated by using the Kamlet-Jacobs equation based on predicted densities and HOFs. Designed tetrazole derivatives show detonation velocity (D) over 8 km/s and detonation pressure (P) of about 32 GPa. Thermal stability was evaluated via bond dissociation energies (BDE) of the weakest C-NO 2 bond at B3LYP/6-31G* level. Charge on the nitro group has been used to assess the sensitivity correlation. Overall, the study implies that designed compounds of this series are found to be stable and expected to be the novel candidates of high energy materials (HEMs).

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“…Various studies have illustrated that N-NO 2 and C-NO 2 are the most probable trigger bonds in nitroaromatic compounds [17,44], and they can easily be ruptured during pyrolysis. All of the predicted BDEs are listed in Table 4.…”

Section: Thermal Stabilitymentioning

confidence: 99%

Molecular design of aminopolynitroazole-based high-energy materials

et al. 2011

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The density functional theory (DFT) was employed to calculate the energetic properties of several aminopolynitroazoles. The calculations were performed to study the effect of amino and nitro substituents on the heats of formation, densities, detonation performances, thermal stabilities, and sensitivity characteristics of azoles. DFT-B3LYP, DFT-B3PW91, and MP2 methods utilizing the basis sets 6-31 G* and 6-311 G (2df, 3p) were adopted to predict HOFs via designed isodesmic reactions. All of the designed aminopolynitroazoles had heats of formation of >220 kJ mol(-1). The crystal densities of the aminopolynitroazoles were predicted with the cvff force field. All of the energetic azoles had densities of >1.83 g/cm(3). The detonation velocities and pressures were evaluated using the Kamlet-Jacobs equations, utilizing the predicted densities and heats of formation. It was found that aminopolynitroazoles have a detonation velocity of about 9.1 km/s and detonation pressure of 36 GPa. The bond dissociation energies for the C-NO(2) and N-NO(2) bonds were analyzed to investigate the stabilities of the designed molecules. The charge on the nitro group was used to assess impact sensitivity in the present study. The results obtained imply that the designed molecules are stable and are expected to be candidates for high-energy materials (HEMs).

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Density functional theory study of piperidine and diazocine compounds

Cited by 48 publications

References 27 publications

Experimental and density functional theory studies of the novel piperidine-containing acetylene glycols

Experimental and density functional theory studies of the novel piperidine-containing acetylene glycols

Computational studies on tetrazole derivatives as potential high energy materials

Molecular design of aminopolynitroazole-based high-energy materials

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