{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,18]],"date-time":"2025-12-18T14:17:06Z","timestamp":1766067426491,"version":"build-2065373602"},"reference-count":62,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2021,9,21]],"date-time":"2021-09-21T00:00:00Z","timestamp":1632182400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["19-13-00013"],"award-info":[{"award-number":["19-13-00013"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["18-29-04006"],"award-info":[{"award-number":["18-29-04006"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["UIDB\/00100\/2020"],"award-info":[{"award-number":["UIDB\/00100\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The 3-Iodo-1-nitrosonaphthalene-2-ol (I-NON) was obtained by the copper(II)-mediated iodination of 1-nitroso-2-naphthol (NON). The suitable reactants and optimized reaction conditions, providing 94% NMR yield of I-NON, included the usage of Cu(OAc)2\u00b7H2O and 1:2:8 CuII\/NON\/I2 molar ratio between the reactants. The obtained I-NON was characterized by elemental analyses (C, H, N), high-resolution ESI+-MS, 1H and 13C{1H} NMR, FTIR, UV-vis spectroscopy, TGA, and X-ray crystallography (XRD). The copper(II) complexes bearing deprotonated I-NON were prepared as follows: cis-[Cu(I-NON\u2013H)(I-NON)](I3) (1) was obtained by the reaction between Cu(NON-H)2 and I2 in CHCl3\/MeOH, while trans-[Cu(I-NON\u2013H)2] (2) was synthesized from I-NON and Cu(OAc)2 in MeOH. Crystals of trans-[Cu(I-NON\u2013H)2(THF)2] (3) and trans-[Cu(I-NON\u2013H)2(Py)2] (4) were precipitated from solutions of 2 in CHCl3\/THF and Py\/CHCl3\/MeOH mixtures, respectively. The structures of 1 and 3\u20134 were additionally verified by X-ray crystallography. The characteristic feature of the structures of 1 and 3 is the presence of intermolecular halogen bonds with the involvement of the iodine center of the metal-bound deprotonated I-NON. The nature of the I\u00b7\u00b7\u00b7I and I\u00b7\u00b7\u00b7O contacts in the structures of 1 and 3, correspondingly, were studied theoretically at the DFT (PBE0-D3BJ) level using the QTAIM, ESP, ELF, NBO, and IGM methods.<\/jats:p>","DOI":"10.3390\/molecules26185708","type":"journal-article","created":{"date-parts":[[2021,9,21]],"date-time":"2021-09-21T22:34:01Z","timestamp":1632263641000},"page":"5708","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Copper(II)-Mediated Iodination of 1-Nitroso-2-naphthol"],"prefix":"10.3390","volume":"26","author":[{"given":"Zarina M.","family":"Efimenko","sequence":"first","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8658-7281","authenticated-orcid":false,"given":"Anton V.","family":"Rozhkov","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"}]},{"given":"Vitalii V.","family":"Suslonov","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5729-6189","authenticated-orcid":false,"given":"Maxim L.","family":"Kuznetsov","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"},{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, 1049-001 Lisbon, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2253-085X","authenticated-orcid":false,"given":"Vadim Yu.","family":"Kukushkin","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"},{"name":"Institute of Chemistry and Pharmaceutical Technologies, Altai State University, 656049 Barnaul, Russia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8692-9627","authenticated-orcid":false,"given":"Nadezhda A.","family":"Bokach","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"}]}],"member":"1968","published-online":{"date-parts":[[2021,9,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"5040","DOI":"10.1039\/D0CE00728E","article-title":"ortho-Substituent effect on the crystal packing and solid state speciation of aromatic C-nitroso compounds","volume":"22","author":"Pike","year":"2020","journal-title":"CrystEngComm"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1037","DOI":"10.1016\/j.bmc.2003.12.010","article-title":"Spirobipyridopyrans, spirobinaphthopyrans, indolinospiropyridopyrans, indolinospironaphthopyrans and indolinospironaphtho-1,4-oxazines: Synthesis, study of X-ray crystal structure, antitumoral and antiviral evaluation","volume":"12","author":"Cetina","year":"2004","journal-title":"Bioorg. 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