{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T00:04:07Z","timestamp":1787011447988,"version":"build-2736575974"},"reference-count":33,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2016,3,5]],"date-time":"2016-03-05T00:00:00Z","timestamp":1457136000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2016,3,5]],"date-time":"2016-03-05T00:00:00Z","timestamp":1457136000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"published-print":{"date-parts":[[2016,4,1]]},"abstract":"<jats:p>\n                    Aryldiazenyl derivatives of salicylic acid and their salts are used as dyes. In these structures, the carboxylate groups are engaged in short contacts with the cations and in hydrogen bonds with water molecules, if present. If both O atoms of the carboxylate group take part in such interactions, the negative charge is delocalized over the two atoms. In the absence of hydrogen bonds and contacts with cations, the negative charge is localized on one of the O atoms. In the crystal structures of tetramethylammonium 2-hydroxy-5-[(\n                    <jats:italic>E<\/jats:italic>\n                    )-(4-nitrophenyl)diazenyl]benzoate and tetramethylammonium 2-hydroxy-5-[(\n                    <jats:italic>E<\/jats:italic>\n                    )-(2-nitrophenyl)diazenyl]benzoate, both C\n                    <jats:sub>4<\/jats:sub>\n                    H\n                    <jats:sub>12<\/jats:sub>\n                    N\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7C\n                    <jats:sub>13<\/jats:sub>\n                    H\n                    <jats:sub>8<\/jats:sub>\n                    N\n                    <jats:sub>3<\/jats:sub>\n                    O\n                    <jats:sub>5<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    , all the interactions between the cations and anions are weak, and their effect on the geometry of the anions is negligible. Under these conditions, the 2-nitro-substituted anion is an almost pure phenol\u2013carboxylate tautomer, whereas in the 4-nitro-substituted anion, the phenolic H atom is shifted towards the carboxylate group, and thus the structure of this anion is intermediate between the phenol\u2013carboxylate and phenolate\u2013carboxylic acid tautomeric forms. The probable formation of such an intermediate form is supported by quantum chemical calculations. Being the characteristic feature of this form, a short distance between the phenolic and carboxylate O atoms is observed in the 4-nitro-substituted anion, as well as in the structures of some 3,5-dinitrosalicylates reported in the literature.\n                  <\/jats:p>","DOI":"10.1107\/s2053229616003193","type":"journal-article","created":{"date-parts":[[2016,3,4]],"date-time":"2016-03-04T10:46:59Z","timestamp":1457088419000},"page":"274-279","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Carboxylate\u2013phenolate tautomerism in 5-[(nitrophenyl)diazenyl]salicylate anions"],"prefix":"10.1107","volume":"72","author":[{"given":"Alexandr V.","family":"Yatsenko","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ksenia A.","family":"Paseshnichenko","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2016,3,5]]},"reference":[{"key":"lg3183_bb1","doi-asserted-by":"crossref","first-page":"S1","DOI":"10.1039\/p298700000s1","volume":"2","author":"Allen","year":"1987","journal-title":"J. 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