Synthesis and Characterization of Secondary Nitrosamines from Secondary Amines Using Sodium Nitrite and p-Toluenesulfonic Acid
We synthesized nitrosamines (R2NNO) with R=iPr (1), nPr (2), nBu (3), and hydroxyethyl (4) from the amine using sodium nitrite/p‐toluenesulfonic acid in CH2Cl2. The rate of formation of 1–4 increases in the direction iPr
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2015-03, Vol.10 (3), p.674-678 |
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| container_title | Chemistry, an Asian journal |
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| creator | Miró Sabaté, Carles Delalu, Henri |
| description | We synthesized nitrosamines (R2NNO) with R=iPr (1), nPr (2), nBu (3), and hydroxyethyl (4) from the amine using sodium nitrite/p‐toluenesulfonic acid in CH2Cl2. The rate of formation of 1–4 increases in the direction iPr |
| doi_str_mv | 10.1002/asia.201403182 |
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Rocket science: This manuscript describes the synthesis and characterization of several nitrosamines (see scheme), which are useful starting materials for the synthesis of 2‐tetrazenes of prospective interest in liquid rocket propulsion.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201403182</identifier><identifier>PMID: 25582458</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>amines ; Chemistry ; energetic materials ; hydrazines ; NMR ; Nuclear magnetic resonance ; sodium ; synthetic methods</subject><ispartof>Chemistry, an Asian journal, 2015-03, Vol.10 (3), p.674-678</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5182-e96c1810ccc838f8a0d07115e3c4e0a1f57b626dd2e94fede2f1dfbd93ea146e3</citedby><cites>FETCH-LOGICAL-c5182-e96c1810ccc838f8a0d07115e3c4e0a1f57b626dd2e94fede2f1dfbd93ea146e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fasia.201403182$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201403182$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25582458$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Miró Sabaté, Carles</creatorcontrib><creatorcontrib>Delalu, Henri</creatorcontrib><title>Synthesis and Characterization of Secondary Nitrosamines from Secondary Amines Using Sodium Nitrite and p-Toluenesulfonic Acid</title><title>Chemistry, an Asian journal</title><addtitle>Chem. Asian J</addtitle><description>We synthesized nitrosamines (R2NNO) with R=iPr (1), nPr (2), nBu (3), and hydroxyethyl (4) from the amine using sodium nitrite/p‐toluenesulfonic acid in CH2Cl2. The rate of formation of 1–4 increases in the direction iPr<nPr<nBu<CH2CH2OH. Compounds 1–3 were obtained as colorless solids, whereas 4 is a bright yellow liquid. Compounds 1–4 were characterized by elemental analysis, MS, IR, and multinuclear NMR (1H, 13C, and 15N) spectroscopies. Additionally, we measured the UV/Vis spectra of all compounds, which show maxima of absorption at approximately 221 nm and molar extinction coefficients between 3043 and 4859 L mol−1 cm−1. We calculated the optimized structures of 1–4 (B3LYP/6‐311+G(d,p)) and computed the NMR spectroscopic chemical shifts and infrared frequencies. Furthermore, we carried out a natural bond orbital (NBO) analysis of the nitrosamine moiety. Lastly, the compounds described in this work are valuable starting materials for the synthesis of 2‐tetrazenes with potential interest to replace highly toxic hydrazines in rocket propulsion.
Rocket science: This manuscript describes the synthesis and characterization of several nitrosamines (see scheme), which are useful starting materials for the synthesis of 2‐tetrazenes of prospective interest in liquid rocket propulsion.</description><subject>amines</subject><subject>Chemistry</subject><subject>energetic materials</subject><subject>hydrazines</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>sodium</subject><subject>synthetic methods</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkM9P2zAUx61paGWF644o0s7pbCdOnGOINn4IdYeC4Ga59vMwNHGxE0E57G-faUrFbadnPX--36fvF6FvBM8IxvSHDFbOKCY5zginn9Ah4QVJ85Lcfd6_KZ-gryE8YMworvgXNKGMcZozfoj-LjZdfw_BhkR2OmnupZeqB29fZW9dlziTLEC5Tku_Sea29y7I1nYQEuNd--GvHrc3wXZ_koXTdmi3vO1h67xOr91qgMgMK-M6q5JaWX2EDoxcBTjezSm6-fXzujlPr36fXTT1VapYjJVCVSjCCVZK8YwbLrHGJSEMMpUDlsSwclnQQmsKVW5AAzVEm6WuMpAkLyCbou-j79q7pwFCLx7c4Lt4UpCCsaqMbbBIzUZKxZjBgxFrb9uYThAs3uoWb3WLfd1RcLKzHZYt6D3-3m8EqhF4tivY_MdO1IuL-qN5Ompt6OFlr5X-URRlVjJxOz8TTdGcXs7LS8GyfxOsnec</recordid><startdate>201503</startdate><enddate>201503</enddate><creator>Miró Sabaté, Carles</creator><creator>Delalu, Henri</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope></search><sort><creationdate>201503</creationdate><title>Synthesis and Characterization of Secondary Nitrosamines from Secondary Amines Using Sodium Nitrite and p-Toluenesulfonic Acid</title><author>Miró Sabaté, Carles ; Delalu, Henri</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5182-e96c1810ccc838f8a0d07115e3c4e0a1f57b626dd2e94fede2f1dfbd93ea146e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>amines</topic><topic>Chemistry</topic><topic>energetic materials</topic><topic>hydrazines</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>sodium</topic><topic>synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miró Sabaté, Carles</creatorcontrib><creatorcontrib>Delalu, Henri</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miró Sabaté, Carles</au><au>Delalu, Henri</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of Secondary Nitrosamines from Secondary Amines Using Sodium Nitrite and p-Toluenesulfonic Acid</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem. Asian J</addtitle><date>2015-03</date><risdate>2015</risdate><volume>10</volume><issue>3</issue><spage>674</spage><epage>678</epage><pages>674-678</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>We synthesized nitrosamines (R2NNO) with R=iPr (1), nPr (2), nBu (3), and hydroxyethyl (4) from the amine using sodium nitrite/p‐toluenesulfonic acid in CH2Cl2. The rate of formation of 1–4 increases in the direction iPr<nPr<nBu<CH2CH2OH. Compounds 1–3 were obtained as colorless solids, whereas 4 is a bright yellow liquid. Compounds 1–4 were characterized by elemental analysis, MS, IR, and multinuclear NMR (1H, 13C, and 15N) spectroscopies. Additionally, we measured the UV/Vis spectra of all compounds, which show maxima of absorption at approximately 221 nm and molar extinction coefficients between 3043 and 4859 L mol−1 cm−1. We calculated the optimized structures of 1–4 (B3LYP/6‐311+G(d,p)) and computed the NMR spectroscopic chemical shifts and infrared frequencies. Furthermore, we carried out a natural bond orbital (NBO) analysis of the nitrosamine moiety. Lastly, the compounds described in this work are valuable starting materials for the synthesis of 2‐tetrazenes with potential interest to replace highly toxic hydrazines in rocket propulsion.
Rocket science: This manuscript describes the synthesis and characterization of several nitrosamines (see scheme), which are useful starting materials for the synthesis of 2‐tetrazenes of prospective interest in liquid rocket propulsion.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25582458</pmid><doi>10.1002/asia.201403182</doi><tpages>5</tpages></addata></record> |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | amines Chemistry energetic materials hydrazines NMR Nuclear magnetic resonance sodium synthetic methods |
| title | Synthesis and Characterization of Secondary Nitrosamines from Secondary Amines Using Sodium Nitrite and p-Toluenesulfonic Acid |
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