Abstract:
1-Aryl-3-(4-bromophenyl)-4,4-dichloro-1,2-diazabuta-1,3- dienes were synthesized via copper-catalyzed reaction of 4-bromobenzaldehyde arylhydrazones with CCl4. X-ray diffraction analysis revealed non-covalent Cl···Br interactions in the crystalline state and formation of 3D supramolecular framework; DFT calculations and topological analysis of the electron density distribution within the framework of Bader's theory (QTAIM method) confirmed these observations. Theoretical calculations showed that highly polarizable dichlorodiazadiene unit is capable of acting as a relatively strong halogen bond donor.
Citation:
N. G. Shikhaliyev, A. M. Maharramov, Kh. N. Bagirova, G. T. Suleymanova, B. D. Tsyrenova, V. G. Nenajdenko, A. S. Novikov, V. N. Khrustalev, A. G. Tskhovrebov, “Supramolecular organic frameworks derived from bromoaryl-substituted dichlorodiazabutadienes via Cl···Br halogen bonding”, Mendeleev Commun., 31:2 (2021), 191–193
Linking options:
https://www.mathnet.ru/eng/mendc875
https://www.mathnet.ru/eng/mendc/v31/i2/p191
This publication is cited in the following 22 articles:
Namiq Q. Shikhaliyev, Aliyar A. Babazade, Gulnar T. Atakishiyeva, Irada M. Shikhaliyeva, Abel M. Maharramov, Victor N. Khrustalev, Zeliha Atioğlu, Mehmet Akkurt, Ajaya Bhattarai, “Crystal structures and Hirshfeld surface analyses of methyl (2Z)-(4-bromophenyl)[2-(4-methylphenyl)hydrazinylidene]acetate, methyl (2Z)-(4-bromophenyl)[2-(3,5-dimethylphenyl)hydrazinylidene]acetate, methyl (2Z)-[2-(4-methoxyphenyl)hydrazinylidene](3-nitrophenyl)acetate, methyl (2E)-(4-chlorophenyl)(2-phenylhydrazinylidene)acetate and methyl (2Z)-[2-(4-bromophenyl)hydrazinylidene](4-chlorophenyl)acetate”, Acta Crystallogr E Cryst Commun, 81:4 (2025), 314
Anna A. Kazakova, Alexey S. Kubasov, Alexander O. Chizhov, Anton P. Novikov, Mikhail A. Volkov, Alexander V. Borisov, Valentine G. Nenajdenko, Evgeny A. Dukhnovsky, Artsiom E. Bely, Maria M. Grishina, Andreii S. Kritchenkov, Rosa M. Gomila, Antonio Frontera, Alexander G. Tskhovrebov, “Perrhenate and pertechnetate complexes of dicationic pyridinium-fused 1,2,4-selenodiazoles featuring Se⋯O chalcogen bonding and anion⋯anion interactions”, Inorganica Chimica Acta, 563 (2024), 121929
Namiq Q. Shikhaliyev, Shafiga A. İbrahimova, Gulnar T. Atakishiyeva, Nigar E. Ahmedova, Gulnara V. Babayeva, Victor N. Khrustalev, Zeliha Atioğlu, Mehmet Akkurt, Ajaya Bhattarai, “Crystal structures and Hirshfeld surface analyses of methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate, methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate and methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate”, Acta Crystallogr E Cryst Commun, 80:2 (2024), 184
I. I. Stoikov, I. S. Antipin, V. A. Burilov, A. R. Kurbangalieva, N. V. Rostovskii, A. S. Pankova, I. A. Balova, Yu. O. Remizov, L. M. Pevzner, M. L. Petrov, A. V. Vasilyev, A. D. Averin, I. P. Beletskaya, V. G. Nenajdenko, E. K. Beloglazkina, S. P. Gromov, S. S. Karlov, T. V. Magdesieva, A. A. Prishchenko, S. V. Popkov, A. O. Terent'ev, G. V. Tsaplin, T. P. Kustova, L. B. Kochetova, N. A. Magdalinova, E. A. Krasnokutskaya, A. V. Nyuchev, Yu. L. Kuznetsova, A. Yu. Fedorov, A. Yu. Egorova, V. S. Grinev, V. V. Sorokin, K. L. Ovchinnikov, E. R. Kofanov, A. V. Kolobov, V. L. Rusinov, G. V. Zyryanov, E. V. Nosov, V. A. Bakulev, N. P. Belskaya, T. V. Berezkina, D. L. Obydennov, V. Ya. Sosnovskikh, S. G. Bakhtin, O. V. Baranova, V. S. Doroshkevich, G. Z. Raskildina, R. M. Sultanova, S. S. Zlotskii, V. D. Dyachenko, I. V. Dyachenko, A. S. Fisyuk, V. V. Konshin, V. V. Dotsenko, E. A. Ivleva, A. N. Reznikov, Yu. N. Klimochkin, D. A. Aksenov, N. A. Aksenov, A. V. Aksenov, V. V. Burmistrov,, “Organic Chemistry in Russian Universities. Achievements of Recent Years”, Russ J Org Chem, 60:8 (2024), 1361
I. I. Stoykov, I. S. Antipin, V. A. Burilov, A. R. Kurbangalieva, N. V. Rostovsky, A. S. Pankova, I. A. Balova, Yu. O. Remizov, L. M. Pevzner, M. L. Petrov, A. V. Vasily, A. D. Averin, I. P. Beletskaya, V. G. Nenaydenko, E. K. Beloglazkina, S. P. Gromov, S. S. Karlov, T. V. Magdesieva, A. A. Prishchenko, S. V. Popkov, A. O. Terentyev, G. V. Tsaplin, T. P. Kustova, L. B. Kochetova, N. A. Magdalinova, E. A. Krasnokutskaya, A. V. Nyuchev, Yu. L. Kuznetsova, A. Yu. Fedorov, A. Yu. Egorova, V. S. Grinev, V. V. Sorokin, K. L. Ovchinnikov, E. R. Kofanov, A. V. Kolobov, V. L. Rusinov, G. V. Zyryanov, E. V. Nosov, V. A. Bakulev, N. P. Belskaya, T. V. Berezkina, D. L. Obydennov, V. Ya. Sosnovskikh, S. G. Bakhtin, O. V. Baranova, V. S. Doroshkevich, G. Z. Raskildina, R. M. Sultanova, S. S. Zlotskiy, V. D. Dyachenko, I. V. Dyachenko, A. S. Fisyuk, V. V. Konshin, V. V. Dotsenko, E. A. Ivleva, A. N. Reznikov, Yu. N. Klimochkin, D. A. Aksenov, N. A. Aksenov, A. V. Aksenov, V. V. Burmistrov, G. M. But, “Organic Chemistry in Russian Universities: Achievements of recent years”, Žurnal organičeskoj himii, 60:2-3 (2024)
Abel Maharramov, Namiq Q. Shikhaliyev, Ayten Qajar, Gulnar T. Atakishiyeva, Ayten Niyazova, Victor N. Khrustalev, Mehmet Akkurt, Sema Öztürk Y{\i}ld{\i}r{\i}m, Ajaya Bhattarai, “Crystal structures and Hirshfeld surface analyses of (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methylphenyl)diazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene and (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(3-methylphenyl)diazene”, Acta Crystallogr E Cryst Commun, 79:7 (2023), 637
Alexander A. Sapronov, Alexey S. Kubasov, Victor N. Khrustalev, Alexey A. Artemjev, Gleb M. Burkin, Evgeny A. Dukhnovsky, Alexander O. Chizhov, Andreii S. Kritchenkov, Rosa M. Gomila, Antonio Frontera, Alexander G. Tskhovrebov, “Se⋯π Chalcogen Bonding in 1,2,4-Selenodiazolium Tetraphenylborate Complexes”, Symmetry, 15:1 (2023), 212
Valentine G. Nenajdenko, Anna A. Kazakova, Alexander S. Novikov, Namig G. Shikhaliyev, Abel M. Maharramov, Ayten M. Qajar, Gulnar T. Atakishiyeva, Aytan A. Niyazova, Victor N. Khrustalev, Alexey V. Shastin, Alexander G. Tskhovrebov, “Copper-Catalyzed Reaction of N-Monosubstituted Hydrazones with CBr4: Unexpected Fragmentation and Mechanistic Study”, Catalysts, 13:8 (2023), 1194
Abel Maharramov, Namiq Q. Shikhaliyev, Afaq Abdullayeva, Gulnar T. Atakishiyeva, Ayten Niyazova, Victor N. Khrustalev, Shahnaz I. Gahramanova, Zeliha Atioğlu, Mehmet Akkurt, Ajaya Bhattarai, “Crystal structure and Hirshfeld surface analysis of 4-azido-2-(3,5-dimethylphenyl)-5-(4-nitrophenyl)-2H-1,2,3-triazole”, Acta Crystallogr E Cryst Commun, 79:10 (2023), 905
Jiangbin Zhong, Jingbo Sun, Kaiqi Ye, Ran Lu, “Halogen effect in photomechanical molecular crystals”, J. Mater. Chem. C, 11:47 (2023), 16452
Mariya V. Grudova, Victor N. Khrustalev, Alexey S. Kubasov, Pavel V. Strashnov, Zhanna V. Matsulevich, Julia M. Lukiyanova, Galina N. Borisova, Andreii S. Kritchenkov, Maria M. Grishina, Alexey A. Artemjev, Ivan V. Buslov, Vladimir K. Osmanov, Valentine G. Nenajdenko, Nguyen Q. Trung, Alexander V. Borisov, Alexander G. Tskhovrebov, “Adducts of 2-Pyridylselenenyl Halides and Nitriles as Novel Supramolecular Building Blocks: Four-Center Se···N Chalcogen Bonding versus Other Weak Interactions”, Crystal Growth & Design, 22:1 (2022), 313
Vladimir K. Osmanov, Evgeniy V. Chipinsky, Victor N. Khrustalev, Alexander S. Novikov, Rizvan Kamiloglu Askerov, Alexander O. Chizhov, Galina N. Borisova, Alexander V. Borisov, Maria M. Grishina, Margarita N. Kurasova, Anatoly A. Kirichuk, Alexander S. Peregudov, Andreii S. Kritchenkov, Alexander G. Tskhovrebov, “Facile Access to 2-Selenoxo-1,2,3,4-tetrahydro-4-quinazolinone Scaffolds and Corresponding Diselenides via Cyclization between Methyl Anthranilate and Isoselenocyanates: Synthesis and Structural Features”, Molecules, 27:18 (2022), 5799
Nikita A. Korobeynikov, Andrey N. Usoltsev, Pavel A. Abramov, Alexander S. Novikov, Maxim N. Sokolov, Sergey A. Adonin, “Bromine-rich tin(IV) halide complexes: Experimental and theoretical examination of Br···Br noncovalent interactions in crystalline state”, Polyhedron, 222 (2022), 115912
Alexander A. Sapronov, Alexey A. Artemjev, Gleb M. Burkin, Victor N. Khrustalev, Alexey S. Kubasov, Valentine G. Nenajdenko, Rosa M. Gomila, Antonio Frontera, Andreii S. Kritchenkov, Alexander G. Tskhovrebov, “Robust Supramolecular Dimers Derived from Benzylic-Substituted 1,2,4-Selenodiazolium Salts Featuring Selenium⋯π Chalcogen Bonding”, IJMS, 23:23 (2022), 14973
Mariya V. Grudova, Alexey S. Kubasov, Victor N. Khrustalev, Alexander S. Novikov, Andreii S. Kritchenkov, Valentine G. Nenajdenko, Alexander V. Borisov, Alexander G. Tskhovrebov, “Exploring Supramolecular Assembly Space of Cationic 1,2,4-Selenodiazoles: Effect of the Substituent at the Carbon Atom and Anions”, Molecules, 27:3 (2022), 1029
Alexey A. Artemjev, Artyom A. Astafiev, Anna V. Vologzhanina, Alexey S. Kubasov, Gleb M. Burkin, Alexander S. Novikov, Andreii S. Kritchenkov, Anatoly A. Kirichuk, Alexander G. Tskhovrebov, “Triarylazoimidazole-ZnII, CdII, and HgII Complexes: Structures, Photophysics, and Antibacterial Properties”, Crystals, 12:5 (2022), 680
Alexey A. Artemjev, Anton P. Novikov, Gleb M. Burkin, Alexander A. Sapronov, Alexey S. Kubasov, Valentine G. Nenajdenko, Victor N. Khrustalev, Alexander V. Borisov, Anatoly A. Kirichuk, Andreii S. Kritchenkov, Rosa M. Gomila, Antonio Frontera, Alexander G. Tskhovrebov, “Towards Anion Recognition and Precipitation with Water-Soluble 1,2,4-Selenodiazolium Salts: Combined Structural and Theoretical Study”, IJMS, 23:12 (2022), 6372
Mariya V. Grudova, Alexander S. Novikov, Alexey S. Kubasov, Victor N. Khrustalev, Anatoly A. Kirichuk, Valentine G. Nenajdenko, Alexander G. Tskhovrebov, “Aurophilic Interactions in Cationic Three-Coordinate Gold(I) Bipyridyl/Isocyanide Complex”, Crystals, 12:5 (2022), 613
Valentine G. Nenajdenko, Namiq G. Shikhaliyev, Abel M. Maharramov, Gulnar T. Atakishiyeva, Aytan A. Niyazova, Naila A. Mammadova, Alexander S. Novikov, Ivan V. Buslov, Victor N. Khrustalev, Alexander G. Tskhovrebov, “Structural Organization of Dibromodiazadienes in the Crystal and Identification of Br···O Halogen Bonding Involving the Nitro Group”, Molecules, 27:16 (2022), 5110
Ivan V. Buslov, Alexander S. Novikov, Victor N. Khrustalev, Mariya V. Grudova, Alexey S. Kubasov, Zhanna V. Matsulevich, Alexander V. Borisov, Julia M. Lukiyanova, Maria M. Grishina, Anatoly A. Kirichuk, Tatiyana V. Serebryanskaya, Andreii S. Kritchenkov, Alexander G. Tskhovrebov, “2-Pyridylselenenyl versus 2-Pyridyltellurenyl Halides: Symmetrical Chalcogen Bonding in the Solid State and Reactivity towards Nitriles”, Symmetry, 13:12 (2021), 2350