1‐(Azidomethyl)‐5H‐Tetrazole: A Powerful New Ligand for Highly Energetic Coordination Compounds
Highly energetic 1‐(azidomethyl)‐5H‐tetrazole (AzMT, 3) has been synthesized and characterized. This completes the series of 1‐(azidoalkyl)‐5H‐tetrazoles represented by 1‐(azidoethyl)‐5H‐tetrazole (AET) and 1‐(azidopropyl)‐5H‐tetrazole (APT). AzMT was thoroughly analyzed by single‐crystal X‐ray diff...
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| description | Highly energetic 1‐(azidomethyl)‐5H‐tetrazole (AzMT, 3) has been synthesized and characterized. This completes the series of 1‐(azidoalkyl)‐5H‐tetrazoles represented by 1‐(azidoethyl)‐5H‐tetrazole (AET) and 1‐(azidopropyl)‐5H‐tetrazole (APT). AzMT was thoroughly analyzed by single‐crystal X‐ray diffraction experiments, elemental analysis, IR spectroscopy and multinuclear (1H, 13C, 14N, 15N) NMR measurements. Several energetic coordination compounds (ECCs) of 3d metals (Mn, Fe, Cu, Zn) and silver in combination with anions such as (per)chlorate, mono‐ and dihydroxy‐trinitrophenolate were prepared, giving insight into the coordination behavior of AzMT as a ligand. The synthesized ECCs were also analyzed by X‐ray diffraction experiments, elemental analysis, and IR spectroscopy. Differential thermal analysis for all compounds was conducted, and the sensitivity towards external stimuli (impact, friction, and ESD) was measured. Due to the high enthalpy of formation of AzMT (+654.5 kJ mol−1), some of the resulting coordination compounds are extremely sensitive, yet are able to undergo deflagration‐to‐detonation transition (DDT) and initiate pentaerythritol tetranitrate (PETN). Therefore, they are to be ranked as primary explosives.
Shortening the alkyl chain in 1‐(Azidoethyl)‐5H‐tetrazole (AET) to a methylene bridge results in the formation of highly sensitive 1‐(azidomethyl)‐5H‐tetrazole (AzMT), which exhibits a greatly increased enthalpy of formation, hence a drastically increased detonation performance is calculated. Like AET, AzMT can be applied as ligand in the energetic coordination compounds (ECC) of several transition metals, showing the characteristics of primary explosives capable of initiating pentaerythritol tetranitrate. The ligand as well as all ECCs are fully characterized. |
| doi_str_mv | 10.1002/chem.202200492 |
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Shortening the alkyl chain in 1‐(Azidoethyl)‐5H‐tetrazole (AET) to a methylene bridge results in the formation of highly sensitive 1‐(azidomethyl)‐5H‐tetrazole (AzMT), which exhibits a greatly increased enthalpy of formation, hence a drastically increased detonation performance is calculated. Like AET, AzMT can be applied as ligand in the energetic coordination compounds (ECC) of several transition metals, showing the characteristics of primary explosives capable of initiating pentaerythritol tetranitrate. The ligand as well as all ECCs are fully characterized.</description><identifier>ISSN: 0947-6539</identifier><identifier>ISSN: 1521-3765</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202200492</identifier><identifier>PMID: 35502815</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>alkylazides ; Anions ; Chemical analysis ; Chemistry ; Chlorate ; Coordination compounds ; Copper ; Deflagration ; Detonation ; Differential thermal analysis ; energetic coordination compounds ; Enthalpy ; External stimuli ; Heavy metals ; Infrared spectroscopy ; initiation ; Iron ; Ligands ; Manganese ; Nitrogen isotopes ; NMR ; Nuclear magnetic resonance ; PETN ; primary explosives ; Silver ; Spectroscopic analysis ; Spectrum analysis ; Synthesis ; tetrazole ; Tetrazoles ; Thermal analysis ; X-ray diffraction ; Zinc</subject><ispartof>Chemistry : a European journal, 2022-07, Vol.28 (38), p.e202200492-n/a</ispartof><rights>2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH</rights><rights>2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.</rights><rights>2022. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-2105-1275 ; 0000-0003-3276-1157 ; 0000-0003-0215-8576 ; 0000-0002-5494-9903 ; 0000-0001-8522-2582</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.202200492$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202200492$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35502815$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kofen, Moritz</creatorcontrib><creatorcontrib>Lommel, Marcus</creatorcontrib><creatorcontrib>Wurzenberger, Maximilian H. H.</creatorcontrib><creatorcontrib>Klapötke, Thomas M.</creatorcontrib><creatorcontrib>Stierstorfer, Jörg</creatorcontrib><title>1‐(Azidomethyl)‐5H‐Tetrazole: A Powerful New Ligand for Highly Energetic Coordination Compounds</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Highly energetic 1‐(azidomethyl)‐5H‐tetrazole (AzMT, 3) has been synthesized and characterized. This completes the series of 1‐(azidoalkyl)‐5H‐tetrazoles represented by 1‐(azidoethyl)‐5H‐tetrazole (AET) and 1‐(azidopropyl)‐5H‐tetrazole (APT). AzMT was thoroughly analyzed by single‐crystal X‐ray diffraction experiments, elemental analysis, IR spectroscopy and multinuclear (1H, 13C, 14N, 15N) NMR measurements. Several energetic coordination compounds (ECCs) of 3d metals (Mn, Fe, Cu, Zn) and silver in combination with anions such as (per)chlorate, mono‐ and dihydroxy‐trinitrophenolate were prepared, giving insight into the coordination behavior of AzMT as a ligand. The synthesized ECCs were also analyzed by X‐ray diffraction experiments, elemental analysis, and IR spectroscopy. Differential thermal analysis for all compounds was conducted, and the sensitivity towards external stimuli (impact, friction, and ESD) was measured. Due to the high enthalpy of formation of AzMT (+654.5 kJ mol−1), some of the resulting coordination compounds are extremely sensitive, yet are able to undergo deflagration‐to‐detonation transition (DDT) and initiate pentaerythritol tetranitrate (PETN). Therefore, they are to be ranked as primary explosives.
Shortening the alkyl chain in 1‐(Azidoethyl)‐5H‐tetrazole (AET) to a methylene bridge results in the formation of highly sensitive 1‐(azidomethyl)‐5H‐tetrazole (AzMT), which exhibits a greatly increased enthalpy of formation, hence a drastically increased detonation performance is calculated. Like AET, AzMT can be applied as ligand in the energetic coordination compounds (ECC) of several transition metals, showing the characteristics of primary explosives capable of initiating pentaerythritol tetranitrate. The ligand as well as all ECCs are fully characterized.</description><subject>alkylazides</subject><subject>Anions</subject><subject>Chemical analysis</subject><subject>Chemistry</subject><subject>Chlorate</subject><subject>Coordination compounds</subject><subject>Copper</subject><subject>Deflagration</subject><subject>Detonation</subject><subject>Differential thermal analysis</subject><subject>energetic coordination compounds</subject><subject>Enthalpy</subject><subject>External stimuli</subject><subject>Heavy metals</subject><subject>Infrared spectroscopy</subject><subject>initiation</subject><subject>Iron</subject><subject>Ligands</subject><subject>Manganese</subject><subject>Nitrogen isotopes</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>PETN</subject><subject>primary explosives</subject><subject>Silver</subject><subject>Spectroscopic analysis</subject><subject>Spectrum analysis</subject><subject>Synthesis</subject><subject>tetrazole</subject><subject>Tetrazoles</subject><subject>Thermal analysis</subject><subject>X-ray diffraction</subject><subject>Zinc</subject><issn>0947-6539</issn><issn>1521-3765</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNpdkc9uEzEQxi0EoqFw5YhW4lIOW_xnba85IEVRaJBS4FDOlmPPJq686-DdJUpPfYQ-I09SR20j4DKjb-anTzP6EHpL8DnBmH60G2jPKaYU40rRZ2hCOCUlk4I_RxOsKlkKztQJetX31xhjJRh7iU4Y55jWhE8QkD-3d2fTG-9iC8NmHz5kzRe5XMGQzE0M8KmYFj_iDlIzhuIb7IqlX5vOFU1MxcKvN2FfzDtIaxi8LWYxJuc7M_jYZdFu49i5_jV60ZjQw5vHfop-fplfzRbl8vvF19l0WW5ZXdFS0dqCdASvGFC7AmGVlFXjRM2FYcLVjjDBqoYDa7ih1Aq5MqqxtbGUOAvsFH1-8N2OqxbypMs_BL1NvjVpr6Px-t9N5zd6HX9rVWFcK5wNzh4NUvw1Qj_o1vcWQjAdxLHXVHBFqaT1AX3_H3odx9Tl93QGiJBKMZmpd39fdDzlKYEMqAdg5wPsj3uC9SFffchXH_PVs8X88qjYPSDonOg</recordid><startdate>20220706</startdate><enddate>20220706</enddate><creator>Kofen, Moritz</creator><creator>Lommel, Marcus</creator><creator>Wurzenberger, Maximilian H. H.</creator><creator>Klapötke, Thomas M.</creator><creator>Stierstorfer, Jörg</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-2105-1275</orcidid><orcidid>https://orcid.org/0000-0003-3276-1157</orcidid><orcidid>https://orcid.org/0000-0003-0215-8576</orcidid><orcidid>https://orcid.org/0000-0002-5494-9903</orcidid><orcidid>https://orcid.org/0000-0001-8522-2582</orcidid></search><sort><creationdate>20220706</creationdate><title>1‐(Azidomethyl)‐5H‐Tetrazole: A Powerful New Ligand for Highly Energetic Coordination Compounds</title><author>Kofen, Moritz ; Lommel, Marcus ; Wurzenberger, Maximilian H. H. ; Klapötke, Thomas M. ; Stierstorfer, Jörg</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p3842-928ce7d10b3e2cbe6c9774fd6856a36d8d13634f5e3f5a22c67ba9fc8ac21dce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>alkylazides</topic><topic>Anions</topic><topic>Chemical analysis</topic><topic>Chemistry</topic><topic>Chlorate</topic><topic>Coordination compounds</topic><topic>Copper</topic><topic>Deflagration</topic><topic>Detonation</topic><topic>Differential thermal analysis</topic><topic>energetic coordination compounds</topic><topic>Enthalpy</topic><topic>External stimuli</topic><topic>Heavy metals</topic><topic>Infrared spectroscopy</topic><topic>initiation</topic><topic>Iron</topic><topic>Ligands</topic><topic>Manganese</topic><topic>Nitrogen isotopes</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>PETN</topic><topic>primary explosives</topic><topic>Silver</topic><topic>Spectroscopic analysis</topic><topic>Spectrum analysis</topic><topic>Synthesis</topic><topic>tetrazole</topic><topic>Tetrazoles</topic><topic>Thermal analysis</topic><topic>X-ray diffraction</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kofen, Moritz</creatorcontrib><creatorcontrib>Lommel, Marcus</creatorcontrib><creatorcontrib>Wurzenberger, Maximilian H. H.</creatorcontrib><creatorcontrib>Klapötke, Thomas M.</creatorcontrib><creatorcontrib>Stierstorfer, Jörg</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>PubMed</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kofen, Moritz</au><au>Lommel, Marcus</au><au>Wurzenberger, Maximilian H. H.</au><au>Klapötke, Thomas M.</au><au>Stierstorfer, Jörg</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1‐(Azidomethyl)‐5H‐Tetrazole: A Powerful New Ligand for Highly Energetic Coordination Compounds</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2022-07-06</date><risdate>2022</risdate><volume>28</volume><issue>38</issue><spage>e202200492</spage><epage>n/a</epage><pages>e202200492-n/a</pages><issn>0947-6539</issn><issn>1521-3765</issn><eissn>1521-3765</eissn><abstract>Highly energetic 1‐(azidomethyl)‐5H‐tetrazole (AzMT, 3) has been synthesized and characterized. This completes the series of 1‐(azidoalkyl)‐5H‐tetrazoles represented by 1‐(azidoethyl)‐5H‐tetrazole (AET) and 1‐(azidopropyl)‐5H‐tetrazole (APT). AzMT was thoroughly analyzed by single‐crystal X‐ray diffraction experiments, elemental analysis, IR spectroscopy and multinuclear (1H, 13C, 14N, 15N) NMR measurements. Several energetic coordination compounds (ECCs) of 3d metals (Mn, Fe, Cu, Zn) and silver in combination with anions such as (per)chlorate, mono‐ and dihydroxy‐trinitrophenolate were prepared, giving insight into the coordination behavior of AzMT as a ligand. The synthesized ECCs were also analyzed by X‐ray diffraction experiments, elemental analysis, and IR spectroscopy. Differential thermal analysis for all compounds was conducted, and the sensitivity towards external stimuli (impact, friction, and ESD) was measured. Due to the high enthalpy of formation of AzMT (+654.5 kJ mol−1), some of the resulting coordination compounds are extremely sensitive, yet are able to undergo deflagration‐to‐detonation transition (DDT) and initiate pentaerythritol tetranitrate (PETN). Therefore, they are to be ranked as primary explosives.
Shortening the alkyl chain in 1‐(Azidoethyl)‐5H‐tetrazole (AET) to a methylene bridge results in the formation of highly sensitive 1‐(azidomethyl)‐5H‐tetrazole (AzMT), which exhibits a greatly increased enthalpy of formation, hence a drastically increased detonation performance is calculated. Like AET, AzMT can be applied as ligand in the energetic coordination compounds (ECC) of several transition metals, showing the characteristics of primary explosives capable of initiating pentaerythritol tetranitrate. The ligand as well as all ECCs are fully characterized.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>35502815</pmid><doi>10.1002/chem.202200492</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-2105-1275</orcidid><orcidid>https://orcid.org/0000-0003-3276-1157</orcidid><orcidid>https://orcid.org/0000-0003-0215-8576</orcidid><orcidid>https://orcid.org/0000-0002-5494-9903</orcidid><orcidid>https://orcid.org/0000-0001-8522-2582</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | alkylazides Anions Chemical analysis Chemistry Chlorate Coordination compounds Copper Deflagration Detonation Differential thermal analysis energetic coordination compounds Enthalpy External stimuli Heavy metals Infrared spectroscopy initiation Iron Ligands Manganese Nitrogen isotopes NMR Nuclear magnetic resonance PETN primary explosives Silver Spectroscopic analysis Spectrum analysis Synthesis tetrazole Tetrazoles Thermal analysis X-ray diffraction Zinc |
| title | 1‐(Azidomethyl)‐5H‐Tetrazole: A Powerful New Ligand for Highly Energetic Coordination Compounds |
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