{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T01:46:25Z","timestamp":1760233585523,"version":"build-2065373602"},"reference-count":48,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2021,1,26]],"date-time":"2021-01-26T00:00:00Z","timestamp":1611619200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003443","name":"Ministry of Education and Science of the Russian Federation","doi-asserted-by":"publisher","award":["075-03-2020-223 (FSSF-2020-0017"],"award-info":[{"award-number":["075-03-2020-223 (FSSF-2020-0017"]}],"id":[{"id":"10.13039\/501100003443","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia, Portugal","award":["Instituto Superior T\u00e9cnico DL 57\/2016 and L 57\/2017 Program, Contracts no: IST-ID\/85\/2018 and IST-ID\/110\/2018","UIDB\/00100\/2020"],"award-info":[{"award-number":["Instituto Superior T\u00e9cnico DL 57\/2016 and L 57\/2017 Program, Contracts no: IST-ID\/85\/2018 and IST-ID\/110\/2018","UIDB\/00100\/2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Crystals"],"abstract":"<jats:p>A series of 4,5-dibromo-2-(4-substituted phenyl)hexahydro-3a,6-epoxyisoindol-1(4H)-ones were synthesized by reaction of the corresponding 2-(4-substituted phenyl)-2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1(6H)-ones with [(Me2NCOMe)2H]Br3 in dry chloroform under reflux for 3\u22125 h. In contrast to the 4-F and 4-Cl substituents, one of the bromine atoms of the isoindole moiety behaves as a halogen bond donor in the formation of intermolecular halogen bonding in the 4-H, 4-Br and 4-I analogues. Not only intermolecular hydrogen bonds, but also Ha\u22efHa and Ha\u22ef\u03c0 types of halogen bonds in the 4-H, 4-Br, and 4-I compounds, contribute to the formation of supramolecular architectures leading to 2D or 3D structures.<\/jats:p>","DOI":"10.3390\/cryst11020112","type":"journal-article","created":{"date-parts":[[2021,1,26]],"date-time":"2021-01-26T08:29:16Z","timestamp":1611649756000},"page":"112","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Role of Halogen Substituents on Halogen Bonding in 4,5-DiBromohexahydro-3a,6-Epoxyisoindol-1(4H)-ones"],"prefix":"10.3390","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1415-8012","authenticated-orcid":false,"given":"Atash","family":"Gurbanov","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisbon, Portugal"},{"name":"Department of Chemistry, Baku State University, Z. Khalilov Str. 23, Baku 1148, Azerbaijan"}]},{"given":"Dmitriy","family":"Mertsalov","sequence":"additional","affiliation":[{"name":"Organic Chemistry Department, Peoples\u2019 Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, 117198 Moscow, Russia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0289-0831","authenticated-orcid":false,"given":"Fedor","family":"Zubkov","sequence":"additional","affiliation":[{"name":"Organic Chemistry Department, Peoples\u2019 Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, 117198 Moscow, Russia"}]},{"given":"Maryana","family":"Nadirova","sequence":"additional","affiliation":[{"name":"Organic Chemistry Department, Peoples\u2019 Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, 117198 Moscow, Russia"}]},{"given":"Eugeniya","family":"Nikitina","sequence":"additional","affiliation":[{"name":"Organic Chemistry Department, Peoples\u2019 Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, 117198 Moscow, Russia"}]},{"given":"Hieu","family":"Truong","sequence":"additional","affiliation":[{"name":"Institute of Research and Development, Duy Tan University, Danang 550000, Vietnam"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6363-5535","authenticated-orcid":false,"given":"Mikhail","family":"Grigoriev","sequence":"additional","affiliation":[{"name":"Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Pr. 31, Bld. 4, 119071 Moscow, Russia"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9175-7583","authenticated-orcid":false,"given":"Vladimir","family":"Zaytsev","sequence":"additional","affiliation":[{"name":"Organic Chemistry Department, Peoples\u2019 Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, 117198 Moscow, Russia"}]},{"given":"Kamran","family":"Mahmudov","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisbon, Portugal"},{"name":"Department of Chemistry, Baku State University, Z. Khalilov Str. 23, Baku 1148, Azerbaijan"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8323-888X","authenticated-orcid":false,"given":"Armando","family":"Pombeiro","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisbon, Portugal"},{"name":"Organic Chemistry Department, Peoples\u2019 Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, 117198 Moscow, Russia"}]}],"member":"1968","published-online":{"date-parts":[[2021,1,26]]},"reference":[{"key":"ref_1","unstructured":"Metrangolo, P., and Resnati, G. (2010). 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