Pentazole chemistry: the mechanism of the reaction of aryldiazonium chlorides with azide ion at −80 °C: concerted versus stepwise formation of arylpentazoles, detection of a pentazene intermediate, a combined 1H and 15N NMR experimental and ab initio theoretical study

Butler, R. N.; Fox, Anthony; Collier, Seamus; Burke, Luke A.

doi:10.1039/a804040k

Cited by 51 publications

(64 citation statements)

References 10 publications

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“…[25][26][27] The stability of many aryl pentazoles is well established; their decomposition barriers are typically around 20 kcal mol À1 . [25,[28][29][30] Other pentazole compounds are also known. Hammerl and Klapçtke have, for instance, shown the existence of tetrazolylpentazole by using low-temperature 15 N/ 1 H NMR spectroscopy.…”

Section: Pentazolesmentioning

confidence: 99%

Kinetic Stability and Propellant Performance of Green Energetic Materials

Rahm

Brinck

2010

Chemistry A European J

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Outside contact: Cells in multicellular organisms regulate their adhesion through specialized integrin receptors, which relay signals bidirectionally between the inside and outside of cells. The transmembrane domains (see picture, blue; the integrin–talin complex is red and green) of integrins are the center of the signaling process. Recently, structures of these domains have been reported that shed light on the signal transduction mechanism.

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Section: Pentazolesmentioning

confidence: 99%

Kinetic Stability and Propellant Performance of Green Energetic Materials

Rahm

Brinck

2010

Chemistry A European J

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“…If one assumes that the actual bond lengths and frequencies fall between the uncorrelated and the correlated values, the fit between calculated and observed data becomes satisfactory. These results, together with our previous study of the SO 2 F -anion, 42 demonstrate the difficulties associated with the accurate calculation of highly ionic, long bonds. In view of the significant discrepancies between the observed and calculated frequencies, the calculated force fields have not been included in this paper.…”

Section: Introductionmentioning

confidence: 78%

“…The frequencies calculated by us for ν 1 and ν 3 are in reasonable agreement with those previously calculated at the CASPT2 level 17 and at the CEPA level. 42 N 5 -. For this ion, we used the frequencies calculated at the CCSD(T)/aug-cc-pVDZ level for the zero-point energy calculation as there are no experimental values available.…”

Section: Enthalpies Of Formation Of Gas-phase N3 N3 - N5 + and N5mentioning

confidence: 99%

“…35,40 The value for the ν 2 bending frequency for this ion has been measured in the solid state, and a free space estimate for ν 1 has been obtained based on the spectrum measured for the solid. 41,42 For this ion, we used the experimental frequencies for the zero-point energy determination. Use of the theoretical frequencies introduces a difference of 0.19 kcal/mol because the calculated bend and antisymmetric stretch are ∼50 cm -1 lower than the experimental values.…”

Section: Enthalpies Of Formation Of Gas-phase N3 N3 - N5 + and N5mentioning

confidence: 99%

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History of the AFRL/USC DARPA Program on Polynitrogen Chemistry. Volume 2

Vij¹

2004

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Public reporting burden for this collection of information is estimated to average 1 hour per response, including the time for reviewing instructions, searching existing data sources, gathering and maintaining the data needed, and completing and reviewing this collection of information. Send comments regarding this burden estimate or any other aspect of this collection of information, including suggestions for reducing this burden to Department of Defense, Washington Headquarters Services, Directorate for Information Operations and Reports (0704-0188), 1215 Jefferson Davis Highway, Suite 1204, Arlington, VA 22202-4302. Respondents should be aware that notwithstanding any other provision of law, no person shall be subject to any penalty for failing to comply with a collection of information if it does not display a currently valid OMB control number. PLEASE DO NOT RETURN YOUR FORM TO THE ABOVE ADDRESS. REPORT DATE (DD-MM-YYYY) 08-03-2004 REPORT TYPEFinal Technical Report, Vol. 2 (From -To) DATES COVERED SPONSORING / MONITORING AGENCY NAME(S) AND ADDRESS(ES) 10. SPONSOR/MONITOR'S ACRONYM(S)Air Force Research Laboratory (AFMC) XC AFRL/PRSP SPONSOR/MONITOR'S REPORT10 E. Saturn Blvd. NUMBER(S)Edwards AFB CA 93524-7680 AFRL-PR-ED-TR-2004-0041, Vol. 2 DISTRIBUTION / AVAILABILITY STATEMENTApproved for public release; distribution unlimited. SUPPLEMENTARY NOTESThis report is Volume 2 of 2 volumes. Vol 1 is entitled, "The Solid Gas Singlet Delta Oxygen Generator." ABSTRACTIn the course of the High Energy Density Matter (HEDM) Program, which was initiated in 1986 by the Air Force, the potential of polynitrogen compounds for HEDM was recognized by numerous theoretical studies. However, no systematic efforts were undertaken to synthesize any of the potential candidates predicted by the theoreticians. This changed in 1998, when Dr. Oestmark from the Swedish Defense Research Agency proposed to DARPA an experimental study to prepare tetrahedral N 4 . In response to this proposal and upon urging from the Air Force Research Laboratory, DARPA issued a broad solicitation for experimental efforts and funded eight programs in the polynitrogen area. One of these programs was the effort at the Air Force Research Laboratory at Edwards Air Force Base. This effort was led by Karl Christe, who is also a Research Professor at the Loker Research Institute of the University of Southern California in Los Angeles, CA, and was expanded one year later to include a program at USC. Because of the overlap and close cooperation between these two programs, the results are summarized in a single report. SUBJECT TERMShigh energy density matter; HEDM; polynitrogen; chemistry; tetrahedral N4 NOTICEWhen U.S. Government drawings, specifications, or other data are used for any purpose other than a definitely related Government procurement operation, the fact that the Government may have formulated, furnished, or in any way supplied the said drawings, specifications, or other data, is not to be regarded by implication or otherwise, or in any way licensi...

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“…On reaction of an azide ion with an aryl diazonium compound, three open-chain ArN 5 compounds are formed. 26 One isomer (Z, E) decomposes instantly to phenylazide and dinitrogen, another (E, E) can rearrange to a third isomer (E, Z), which can also be formed directly and undergoes cyclization to form a pentazole. Decomposition follows a different mechanism: phenylpentazole is involved in a 1,3-dipolar cycloreversion with elimination of dinitrogen to form phenylazide.…”

mentioning

confidence: 99%

Nitrogen: Inorganic ChemistryBased in part on the article Nitrogen: Inorganic Chemistry by Harry H. Sisler which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

Hammerl¹,

Klap��tke²

2005

Encyclopedia of Inorganic Chemistry

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The chemistry of nitrogen and its compounds with hydrogen, oxygen, and halogens is discussed in this article. The high stability of the nitrogen–nitrogen triple bond in dinitrogen in comparison with nitrogen–nitrogen single or double bonds makes polynitrogen compounds promising, highly energetic materials. Recently, several new polynitrogen species have been detected experimentally and salts of the polynitrogen cation N 5 + have been isolated in bulk. Salts of the azide anion N 3 − are already used as highly energetic materials. Binary compounds of nitrogen and hydrogen include ammonia, hydrazine, and several metastable species with nitrogen–nitrogen bonds. Ammonia, which is the starting material for all industrially produced nitrogen compounds, is probably the most important industrial chemical. Most of the ammonia produced is used as fertilizer, whereas hydrazine is used as an energetic material. The monomeric nitrogen oxides are among the most simple odd‐electron molecules and play an important role in the chemistry of the atmosphere. In combustion engines, huge amounts of nitric oxide are formed, which influence the ozone cycle both in the troposphere and in the stratosphere. Nitric oxide is a chemical messenger in biological systems and it helps to regulate a diverse array of physiological processes, such as neurotransmission, blood pressure and blood clot prevention. Oxoacids of nitrogen include hydroxylamine, nitrous acid, and nitric acid. Nitric acid is a major industrial chemical, which is primarily used for nitrate fertilizer production. Hydroxylamine is a starting material for the production of polyamide synthetics. Chlorine, bromine, and iodine halogen nitrogen compounds include halogensubstituted derivatives of ammonia, hydrazine, and diimine. They are unstable species that decompose to molecules in excited states. Nitrogen fluorides are thermodynamically more stable than the other nitrogen halides. Ternary compounds of nitrogen, oxygen, and halogens include nitrosyl‐ and nitrylhalides as well as the halogen nitrates. The stability of these compounds decreases from fluorine to iodine.

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Pentazole chemistry: the mechanism of the reaction of aryldiazonium chlorides with azide ion at −80 °C: concerted versus stepwise formation of arylpentazoles, detection of a pentazene intermediate, a combined 1H and 15N NMR experimental and ab initio theoretical study

Cited by 51 publications

References 10 publications

Kinetic Stability and Propellant Performance of Green Energetic Materials

Kinetic Stability and Propellant Performance of Green Energetic Materials

History of the AFRL/USC DARPA Program on Polynitrogen Chemistry. Volume 2

Nitrogen: Inorganic ChemistryBased in part on the article Nitrogen: Inorganic Chemistry by Harry H. Sisler which appeared in theEncyclopedia of Inorganic Chemistry, First Edition.

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