Experimental and DFT study of azo-bis-cyanuric chloride polar Diels-Alder reaction with a number of dienes. Ways of further modification of the obtained products

Karkhut, Andriy; Polovkovych, Svyatoslav; Novikov, Volodymyr

Full metadata record

DC Field	Value	Language
dc.contributor.author	Karkhut, Andriy
dc.contributor.author	Polovkovych, Svyatoslav
dc.contributor.author	Novikov, Volodymyr
dc.date.accessioned	2019-01-29T12:53:42Z	-
dc.date.available	2019-01-29T12:53:42Z	-
dc.date.created	2018-01-20
dc.date.issued	2018-01-20
dc.identifier.citation	Karkhut A. Experimental and DFT study of azo-bis-cyanuric chloride polar Diels-Alder reaction with a number of dienes. Ways of further modification of the obtained products / Andriy Karkhut, Svyatoslav Polovkovych, Volodymyr Novikov // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2-18. — Vol 12. — No 1. — P. 18–23.
dc.identifier.uri	https://ena.lpnu.ua/handle/ntb/43927	-
dc.description.abstract	Була проведена та досліджена на B3LYP/6-31G(d,p) рівні реакція Дільса-Альдера азо-біс- ціанурхлориду як електрофільного дієнофілу з рядом дієнів з різною нуклеофільністю, а саме 2,3-диметилбутадієну, 2-ме- тилбутадієну і 1-ацетоксибутадієну. Визначено, що реакція проходить за м’яких умов та з високими виходами. Обчислені глобальні та локальні індекси реакційності, а також геометрії перехідних станів та енергії активації. Вивчені напрямки подальшої модифікації одержаних продуктів заміщенням атомів хлору. Встановлено, що сполуки є стійкими в лужних умовах, але швидко руйнуються у присутності кислот.
dc.description.abstract	The reaction of azo-bis-cyanuric chloride as strong electrophilic aza-dienophile in Diels-Alder cycloaddition with a number of dienes of different nucleophilicity, namely 2,3-dimethylbutadiene, 2-methylbutadiene and 1-acethoxybutadiene, was carried out and computationally analyzed on B3LYP/6-31G(d,p) level. Local and global reactivity indices, based on FMO theory, as well as TS geometries and activation energies were calculated. Reaction proceeds rapidly with high yields and in mild conditions. Ways of products further modification by chlorine atoms substitution were also studied. Compounds were found to be stable in alkaline conditions but rapidly decompose in the presence of acids.
dc.format.extent	18-23
dc.language.iso	en
dc.publisher	Lviv Politechnic Publishing House
dc.relation.ispartof	Chemistry & Chemical Technology, 1 (12), 2-18
dc.relation.uri	https://doi.org/10.3987/REV-13-SR(S)3
dc.relation.uri	https://doi.org/10.4172/2161-0444.1000255
dc.relation.uri	https://doi.org/10.1002/jhet.890
dc.relation.uri	https://doi.org/10.1002/jhet.5570130427
dc.relation.uri	https://doi.org/10.1038/nprot.2014.042
dc.relation.uri	https://doi.org/10.1002/qua.24481
dc.relation.uri	https://doi.org/10.1021/ja983494x
dc.relation.uri	https://doi.org/10.1016/S0040-4020(02)00410-6
dc.relation.uri	https://doi.org/10.1063/1.464913
dc.relation.uri	https://doi.org/10.1103/PhysRevB.37.785
dc.relation.uri	https://doi.org/10.1002/jcc.10189
dc.relation.uri	https://doi.org/10.1016/S0009-2614(99)00325-5
dc.relation.uri	https://doi.org/10.1002/chem.200903008
dc.subject	реакція Дільса-Альдера
dc.subject	DFT розра- хунки
dc.subject	1
dc.subject	3
dc.subject	5-триазин
dc.subject	конформаційний аналіз
dc.subject	Diels-Alder reaction
dc.subject	DFT calculations
dc.subject	1
dc.subject	3
dc.subject	5-triazine
dc.subject	conformational analysis
dc.title	Experimental and DFT study of azo-bis-cyanuric chloride polar Diels-Alder reaction with a number of dienes. Ways of further modification of the obtained products
dc.title.alternative	Експериментальні та DFT-дослідження полярної реакції Дільса-Альдера азо-біс- ціанурхлориду з рядом дієнів. Шляхи подальшоїмодифікації одержаних продуктів
dc.type	Article
dc.rights.holder	© Національний університет „Львівська політехніка“, 2018
dc.rights.holder	© Karkhut A., Polovkovych S., Novikov V., 2018
dc.contributor.affiliation	Lviv Polytechnic National University
dc.format.pages	6
dc.identifier.citationen	Karkhut A. Experimental and DFT study of azo-bis-cyanuric chloride polar Diels-Alder reaction with a number of dienes. Ways of further modification of the obtained products / Andriy Karkhut, Svyatoslav Polovkovych, Volodymyr Novikov // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2-18. — Vol 12. — No 1. — P. 18–23.
dc.relation.references	[1] CarruthersW.: Cycloaddition Reactions in Organic Synthesis. Pergamon Press, Oxford 1990.
dc.relation.references	[2] Fringuelli F., Taticchi A.: The Diels-Alder Reaction. J. Wiley& Sons, Chichester 2002.
dc.relation.references	[3] Tšupova S., Mäeorg U.: Heterocycles, 2014, 88, 129.https://doi.org/10.3987/REV-13-SR(S)3
dc.relation.references	[4] Liu B., Sun T., Zhou Z., Du L.:Med. Chem., 2015, 5, 131.https://doi.org/10.4172/2161-0444.1000255
dc.relation.references	[5] Polovkovych S., Karkhut A., Marintsova N., Lesyk R. et al.: J. Heterocyclic Chem., 2013, 50, 1419.https://doi.org/10.1002/jhet.890
dc.relation.references	[6] Loew P., Weis C.: J. Heterocyclic Chem., 1976, 13, 829.https://doi.org/10.1002/jhet.5570130427
dc.relation.references	[7]Willoughby P., JansmaM., Hoye T.: Nature Protocols, 2014, 9,643. https://doi.org/10.1038/nprot.2014.042
dc.relation.references	[8] Bochevarov A., Harder E., Hughes T. et al.: Int. J. Quantum Chem., 2013, 113, 2110. https://doi.org/10.1002/qua.24481
dc.relation.references	[9] Parr R., Von Szentpaly L., Liu S.: J. Am. Chem. Soc., 1999, 121,1922. https://doi.org/10.1021/ja983494x
dc.relation.references	[10] Domingo L., Aurell M., Perez P., Contreras R.: Tetrahedron,2002, 58, 4417. https://doi.org/10.1016/S0040-4020(02)00410-6
dc.relation.references	[11] Becke A.: J. Chem. Phys., 1993, 98, 5648.https://doi.org/10.1063/1.464913.
dc.relation.references	[12] Lee C., Yang W., Parr R.: Phys. Rev. B, 1988, 37, 785.https://doi.org/10.1103/PhysRevB.37.785
dc.relation.references	[13] FrischM., Trucks G., Schlegel H., Scuseria G., RobbM., Cheeseman J., Scalmani G., Barone V., Mennucci B., Petersson G., Nakatsuji H., CaricatoM., Li X., Hratchian H., Izmaylov A., Bloino J., Zheng G., Sonnenberg J., HadaM., EharaM., Toyota K., Fukuda R., Hasegawa J., IshidaM., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J., Peralta J., Ogliaro F., BearparkM., Heyd J., Brothers E., Kudin K., Staroverov V., Keith T., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J., Iyengar S.,Tomasi J., Cossi M., Rega N., Millam J., KleneM., Knox J., Cross J., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R., Yazyev O., Austin A., Cammi R., Pomelli C., Ochterski J., Martin R., Morokuma K., Zakrzewski V., Voth G., Salvador P., Dannenberg J., Dapprich S., Daniels A., Farkas O., Foresman J., Ortiz J., Cioslowski J., Fox D., Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT, 2010.
dc.relation.references	[14] Cossi M., Rega N., Scalmani G., Barone V.: J. Comp. Chem.,2003, 24, 669. https://doi.org/10.1002/jcc.10189
dc.relation.references	[15] Chamorro E., Perez P.: J. Chem. Phys., 2005, 123, 114107.
dc.relation.references	[16] Contreras R., Fuentealba P., GalvanM., Perez P.: Chem. Phys. Lett., 1999, 304, 405. https://doi.org/10.1016/S0009-2614(99)00325-5
dc.relation.references	[17] Lakhdar S., Terrier F., Vichard D., Berionni G. et al.: Chem. Eur. J., 2010, 16, 5681. https://doi.org/10.1002/chem.200903008
dc.relation.referencesen	[1] CarruthersW., Cycloaddition Reactions in Organic Synthesis. Pergamon Press, Oxford 1990.
dc.relation.referencesen	[2] Fringuelli F., Taticchi A., The Diels-Alder Reaction. J. Wiley& Sons, Chichester 2002.
dc.relation.referencesen	[3] Tšupova S., Mäeorg U., Heterocycles, 2014, 88, 129.https://doi.org/10.3987/REV-13-SR(S)3
dc.relation.referencesen	[4] Liu B., Sun T., Zhou Z., Du L.:Med. Chem., 2015, 5, 131.https://doi.org/10.4172/2161-0444.1000255
dc.relation.referencesen	[5] Polovkovych S., Karkhut A., Marintsova N., Lesyk R. et al., J. Heterocyclic Chem., 2013, 50, 1419.https://doi.org/10.1002/jhet.890
dc.relation.referencesen	[6] Loew P., Weis C., J. Heterocyclic Chem., 1976, 13, 829.https://doi.org/10.1002/jhet.5570130427
dc.relation.referencesen	[7]Willoughby P., JansmaM., Hoye T., Nature Protocols, 2014, 9,643. https://doi.org/10.1038/nprot.2014.042
dc.relation.referencesen	[8] Bochevarov A., Harder E., Hughes T. et al., Int. J. Quantum Chem., 2013, 113, 2110. https://doi.org/10.1002/qua.24481
dc.relation.referencesen	[9] Parr R., Von Szentpaly L., Liu S., J. Am. Chem. Soc., 1999, 121,1922. https://doi.org/10.1021/ja983494x
dc.relation.referencesen	[10] Domingo L., Aurell M., Perez P., Contreras R., Tetrahedron,2002, 58, 4417. https://doi.org/10.1016/S0040-4020(02)00410-6
dc.relation.referencesen	[11] Becke A., J. Chem. Phys., 1993, 98, 5648.https://doi.org/10.1063/1.464913.
dc.relation.referencesen	[12] Lee C., Yang W., Parr R., Phys. Rev. B, 1988, 37, 785.https://doi.org/10.1103/PhysRevB.37.785
dc.relation.referencesen	[13] FrischM., Trucks G., Schlegel H., Scuseria G., RobbM., Cheeseman J., Scalmani G., Barone V., Mennucci B., Petersson G., Nakatsuji H., CaricatoM., Li X., Hratchian H., Izmaylov A., Bloino J., Zheng G., Sonnenberg J., HadaM., EharaM., Toyota K., Fukuda R., Hasegawa J., IshidaM., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J., Peralta J., Ogliaro F., BearparkM., Heyd J., Brothers E., Kudin K., Staroverov V., Keith T., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J., Iyengar S.,Tomasi J., Cossi M., Rega N., Millam J., KleneM., Knox J., Cross J., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R., Yazyev O., Austin A., Cammi R., Pomelli C., Ochterski J., Martin R., Morokuma K., Zakrzewski V., Voth G., Salvador P., Dannenberg J., Dapprich S., Daniels A., Farkas O., Foresman J., Ortiz J., Cioslowski J., Fox D., Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT, 2010.
dc.relation.referencesen	[14] Cossi M., Rega N., Scalmani G., Barone V., J. Comp. Chem.,2003, 24, 669. https://doi.org/10.1002/jcc.10189
dc.relation.referencesen	[15] Chamorro E., Perez P., J. Chem. Phys., 2005, 123, 114107.
dc.relation.referencesen	[16] Contreras R., Fuentealba P., GalvanM., Perez P., Chem. Phys. Lett., 1999, 304, 405. https://doi.org/10.1016/S0009-2614(99)00325-5
dc.relation.referencesen	[17] Lakhdar S., Terrier F., Vichard D., Berionni G. et al., Chem. Eur. J., 2010, 16, 5681. https://doi.org/10.1002/chem.200903008
dc.citation.volume	12
dc.citation.issue	1
dc.citation.spage	18
dc.citation.epage	23
dc.coverage.placename	Lviv
Appears in Collections:	Chemistry & Chemical Technology. – 2018. – Vol. 12, No. 1

File	Description	Size	Format
2-18v12n1_Karkhut_A-Experimental_and_DFT_study_18-23.pdf		345.13 kB	Adobe PDF	View/Open
2-18v12n1_Karkhut_A-Experimental_and_DFT_study_18-23__COVER.png		522.89 kB	image/png	View/Open

putin IS MURDERER