{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,18]],"date-time":"2026-04-18T09:05:55Z","timestamp":1776503155430,"version":"3.51.2"},"reference-count":27,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2023,8,14]],"date-time":"2023-08-14T00:00:00Z","timestamp":1691971200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100006227","name":"Lawrence Livermore National Laboratory","doi-asserted-by":"publisher","award":["PLS\u201021\u2010FS\u2010036"],"award-info":[{"award-number":["PLS\u201021\u2010FS\u2010036"]}],"id":[{"id":"10.13039\/100006227","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000015","name":"U.S. Department of Energy","doi-asserted-by":"publisher","award":["DE\u2010AC52\u201007NA27344"],"award-info":[{"award-number":["DE\u2010AC52\u201007NA27344"]}],"id":[{"id":"10.13039\/100000015","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Journal of Forensic Sciences"],"published-print":{"date-parts":[[2023,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The benzylation of three low molecular weight <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010disubstituted ethanolamines related to chemical warfare agents (CWAs) to furnish derivatives with improved gas chromatography\u2010mass spectrometry (GC\u2010MS) profiles is described. Due to their low molecular weight and polar nature, <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010disubstituted ethanolamines are notoriously difficult to detect by routine GC\u2010MS analyses during Organisation for the Prohibition of Chemical Weapons (OPCW) proficiency tests (PTs), particularly in scenarios when they are present at low levels (~1\u201310\u2009ppm) amidst more abundant interferences. Our studies revealed that the optimal derivatization conditions involved the treatment of the ethanolamine with benzyl bromide in the presence of an inorganic base (e.g., Na<jats:sub>2<\/jats:sub>CO<jats:sub>3<\/jats:sub>) in dichloromethane at 55\u00b0C for 2\u2009h. This optimized set of conditions was then successfully applied to the derivatization of <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010dimethylethanolamine, <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010diethylethanolamine and <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010diisopropylethanolamine present separately at 1 and 10\u2009\u03bcg\/mL concentrations in a glycerol\u2010rich matrix sample featured in the 48th OPCW PT. The benzylated derivatives of the three ethanolamines possessed retention times long enough to clear the massive glycerol\u2010containing matrix interferences. The protocol herein is introduced as an alternative method for derivatization of these CWA and pharmaceutically important species and should find broad applicability in laboratories where routine forensic analysis is carried out.<\/jats:p>","DOI":"10.1111\/1556-4029.15357","type":"journal-article","created":{"date-parts":[[2023,8,14]],"date-time":"2023-08-14T13:15:21Z","timestamp":1692018921000},"page":"1923-1931","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Practical benzylation of <i>N<\/i>,<i>N<\/i>\u2010substituted ethanolamines related to chemical warfare agents for analysis and detection by electron ionization gas chromatography\u2013mass spectrometry"],"prefix":"10.1111","volume":"68","author":[{"given":"Carlos A.","family":"Valdez","sequence":"first","affiliation":[{"name":"Nuclear and Chemical Sciences Division Lawrence Livermore National Laboratory  Livermore California USA"},{"name":"Global Security Directorate, Lawrence Livermore National Laboratory  Livermore California USA"},{"name":"Forensic Science Center Lawrence Livermore National Laboratory  Livermore California USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander K.","family":"Vu","sequence":"additional","affiliation":[{"name":"Nuclear and Chemical Sciences Division Lawrence Livermore National Laboratory  Livermore California USA"},{"name":"Global Security Directorate, Lawrence Livermore National Laboratory  Livermore California USA"},{"name":"Forensic Science Center Lawrence Livermore National Laboratory  Livermore California USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Saphon","family":"Hok","sequence":"additional","affiliation":[{"name":"Nuclear and Chemical Sciences Division Lawrence Livermore National Laboratory  Livermore California USA"},{"name":"Global Security Directorate, Lawrence Livermore National Laboratory  Livermore California USA"},{"name":"Forensic Science Center Lawrence Livermore National Laboratory  Livermore California USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Armando","family":"Alcaraz","sequence":"additional","affiliation":[{"name":"Nuclear and Chemical Sciences Division Lawrence Livermore National Laboratory  Livermore California USA"},{"name":"Global Security Directorate, Lawrence Livermore National Laboratory  Livermore California USA"},{"name":"Forensic Science Center Lawrence Livermore National Laboratory  Livermore California USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,8,14]]},"reference":[{"key":"e_1_2_11_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100193y"},{"key":"e_1_2_11_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26154631"},{"key":"e_1_2_11_4_1","unstructured":"Organisation for the Prohibition of Chemical Weapons.OPCW annex on chemicals. Available from:https:\/\/www.opcw.org\/. Accessed 4 Apr 2023"},{"key":"e_1_2_11_5_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216\u2010014\u20107931\u20104"},{"key":"e_1_2_11_6_1","doi-asserted-by":"publisher","DOI":"10.1515\/revac\u20102017\u20100007"},{"key":"e_1_2_11_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2013.01.097"},{"key":"e_1_2_11_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/s0021\u20109673(03)00183\u20103"},{"key":"e_1_2_11_9_1","first-page":"2","volume-title":"Handbook of analytical derivatization reactions","author":"Knapp DR","year":"1979"},{"key":"e_1_2_11_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jchromb.2021.122762"},{"key":"e_1_2_11_11_1","doi-asserted-by":"publisher","DOI":"10.1093\/jat\/32.1.51"},{"key":"e_1_2_11_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2011.06.008"},{"key":"e_1_2_11_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.forsciint.2018.04.041"},{"key":"e_1_2_11_14_1","doi-asserted-by":"publisher","DOI":"10.1080\/00032719.2022.2081336"},{"key":"e_1_2_11_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2008.07.008"},{"key":"e_1_2_11_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8AY00396C"},{"key":"e_1_2_11_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2006.04.076"},{"key":"e_1_2_11_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.7012"},{"key":"e_1_2_11_19_1","first-page":"191","volume-title":"Instrumental thin\u2010layer chromatography","author":"Zarzycki PK","year":"2014"},{"key":"e_1_2_11_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/C2RA21214E"},{"key":"e_1_2_11_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja054510a"},{"key":"e_1_2_11_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm8000482"},{"key":"e_1_2_11_23_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216\u2010014\u20107625\u2010y"},{"key":"e_1_2_11_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2009.09.032"},{"key":"e_1_2_11_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.8777"},{"key":"e_1_2_11_26_1","doi-asserted-by":"publisher","DOI":"10.2298\/JSC210312047R"},{"key":"e_1_2_11_27_1","first-page":"100","volume-title":"Protective groups in organic synthesis","author":"Greene T","year":"1991"},{"key":"e_1_2_11_28_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216\u2010021\u201003296\u20106"}],"container-title":["Journal of Forensic Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/am-pdf\/10.1111\/1556-4029.15357","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/1556-4029.15357","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,25]],"date-time":"2023-10-25T18:30:12Z","timestamp":1698258612000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1111\/1556-4029.15357"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,8,14]]},"references-count":27,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2023,11]]}},"alternative-id":["10.1111\/1556-4029.15357"],"URL":"https:\/\/doi.org\/10.1111\/1556-4029.15357","archive":["Portico"],"relation":{},"ISSN":["0022-1198","1556-4029"],"issn-type":[{"value":"0022-1198","type":"print"},{"value":"1556-4029","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,8,14]]},"assertion":[{"value":"2023-06-22","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-08-01","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-08-14","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}