{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T14:31:06Z","timestamp":1791124266818,"version":"4.1.0"},"reference-count":18,"publisher":"American Chemical Society (ACS)","issue":"10","license":[{"start":{"date-parts":[[2015,4,25]],"date-time":"2015-04-25T00:00:00Z","timestamp":1429920000000},"content-version":"vor","delay-in-days":365,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["Contract No. HHSN261200800001E"],"award-info":[{"award-number":["Contract No. HHSN261200800001E"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["Intramural Project No. Z1ABC005673"],"award-info":[{"award-number":["Intramural Project No. Z1ABC005673"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2014,5,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Recent theoretical studies have suggested that the parent diazeniumdiolate ion, H2N\u2013N(O)\u2550NO\u2013 (\u201cdiazeniumdiolated ammonia\u201d), might be stable enough to be isolated and that it could potentially serve as a uniquely advantageous prodrug form of bioactive nitroxyl (HNO). Here, we report on an attempt to isolate its O2-benzylated derivative by aminolysis of the C\u2550N bond in PhC(NH2)\u2550N\u2013N(O)\u2550NOBn. The reaction proved remarkably sluggish in comparison to aminolysis of unsubstituted benzamidine, and the desired product could not be isolated, apparently because of base sensitivity of the NH2 group. Consistent with this interpretation, O-benzylhydroxylamine and N2O were recovered from the reaction mixture in high yields, along with N,N\u2032-dibutylbenzamidine. Theoretical calculations rationalize the observed slow aminolysis by demonstrating that the diazeniumdiolate group greatly suppresses the electrophilicity of the adjacent C\u2550N carbon center, rendering attack at that position endothermic. The data provide significant insights into the challenges inherent to the pursuit of diazeniumdiolated ammonia.<\/jats:p>","DOI":"10.1021\/jo500551n","type":"journal-article","created":{"date-parts":[[2014,4,25]],"date-time":"2014-04-25T09:56:42Z","timestamp":1398419802000},"page":"4512-4516","source":"Crossref","is-referenced-by-count":2,"title":["Aminolysis of an\n                    <i>N<\/i>\n                    -Diazeniumdiolated\nAmidine as an Approach to Diazeniumdiolated Ammonia"],"prefix":"10.1021","volume":"79","author":[{"given":"Debanjan","family":"Biswas","sequence":"first","affiliation":[{"name":"Frederick National Laboratory for Cancer Research , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joseph A.","family":"Hrabie","sequence":"additional","affiliation":[{"name":"Frederick National Laboratory for Cancer Research , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joseph E.","family":"Saavedra","sequence":"additional","affiliation":[{"name":"Frederick National Laboratory for Cancer Research , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhao","family":"Cao","sequence":"additional","affiliation":[{"name":"Frederick National Laboratory for Cancer Research , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Larry K.","family":"Keefer","sequence":"additional","affiliation":[{"name":"Frederick National Laboratory for Cancer Research , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joseph","family":"Ivanic","sequence":"additional","affiliation":[{"name":"Frederick National Laboratory for Cancer Research , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryan J.","family":"Holland","sequence":"additional","affiliation":[{"name":"Frederick National Laboratory for Cancer Research , , , ,","place":["Frederick, Maryland, United States, 21702"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2014,4,25]]},"reference":[{"key":"2026090314103338700_cit1","doi-asserted-by":"crossref","first-page":"1819","DOI":"10.1021\/ja01469a012","volume":"83","author":"Drago","year":"1961","journal-title":"J. Am. Chem. Soc."},{"key":"2026090314103338700_cit2","doi-asserted-by":"crossref","first-page":"1147","DOI":"10.1021\/cb200274r","volume":"6","author":"Keefer","year":"2011","journal-title":"ACS Chem. Biol."},{"key":"2026090314103338700_cit3","doi-asserted-by":"crossref","first-page":"3262","DOI":"10.1021\/ic101736e","volume":"50","author":"Salmon","year":"2011","journal-title":"Inorg. Chem."},{"key":"2026090314103338700_cit4","doi-asserted-by":"crossref","first-page":"6671","DOI":"10.1021\/jp404589p","volume":"117","author":"Wang","year":"2013","journal-title":"J. Phys. Chem. A"},{"key":"2026090314103338700_cit5","doi-asserted-by":"crossref","first-page":"6134","DOI":"10.1021\/jo00049a017","volume":"57","author":"Saavedra","year":"1992","journal-title":"J. Org. Chem."},{"key":"2026090314103338700_cit6","doi-asserted-by":"crossref","first-page":"5799","DOI":"10.1039\/c0cc00849d","volume":"46","author":"Biswas","year":"2010","journal-title":"Chem. 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