Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones
Аутори
Valentić, Nataša V.Vitnik, Željko
Mijin, Dušan
Ušćumlić, Gordana
Todorović, Nina
Juranić, Ivan
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
The C-13 NMR chemical shifts of the C2 carbon atom in the heteroaromatic nuclei of seventeen 5-(3- and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones were determined in deuterated DMSO solution. For quantitative assessment of the substituent effects on the C-13 NMR chemical shifts simple and extended Hammett equations and Swain-Lupton equation were used. The mode of transmission of substituent effects have been discussed in a relation to the geometry of investigated molecules. The geometry data were obtained using semiempirical MNDO-PM6 energy calculations. The observed C-13 NMR substituent chemical shifts were correlated with literature C-13 NMR data for the corresponding 3- and 4-substituted- 2',6'-dimethylazobenzenes and 3- and 4-substituted azobenzenes. A good linear dependence obtained in this way, provided a basis to discuss the influence of the ortho-methyl groups on the degree of coplanarity of azobenzene and pyridone systems, and on the efficiency of transmission of e...lectronic substituent effect from one ring to the other one.
Кључне речи:
LFER models / arylazo pyridone dyes / substituent effects / azo linking group / MNDO-PM6 / DFT-ab initio calculations / uv/vis absorption-spectra / hindered azobenzenes / azo dyes / pm3 / substituent / mechanism / solventsИзвор:
ARKIVOC - Online Journal of Organic Chemistry, 2009, 2009, 13, 227-240Издавач:
- Arkat USA Inc.
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-142063)
- Синтеза, карактеризација и активност органских и координационих једињења и њихова примена у (био)нанотехнологији (RS-142010)
DOI: 10.3998/ark.5550190.0010.d20
ISSN: 1551-7004
WoS: 000277913200020
Scopus: 2-s2.0-77953199233
Институција/група
IHTMTY - JOUR AU - Valentić, Nataša V. AU - Vitnik, Željko AU - Mijin, Dušan AU - Ušćumlić, Gordana AU - Todorović, Nina AU - Juranić, Ivan PY - 2009 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3994 AB - The C-13 NMR chemical shifts of the C2 carbon atom in the heteroaromatic nuclei of seventeen 5-(3- and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones were determined in deuterated DMSO solution. For quantitative assessment of the substituent effects on the C-13 NMR chemical shifts simple and extended Hammett equations and Swain-Lupton equation were used. The mode of transmission of substituent effects have been discussed in a relation to the geometry of investigated molecules. The geometry data were obtained using semiempirical MNDO-PM6 energy calculations. The observed C-13 NMR substituent chemical shifts were correlated with literature C-13 NMR data for the corresponding 3- and 4-substituted- 2',6'-dimethylazobenzenes and 3- and 4-substituted azobenzenes. A good linear dependence obtained in this way, provided a basis to discuss the influence of the ortho-methyl groups on the degree of coplanarity of azobenzene and pyridone systems, and on the efficiency of transmission of electronic substituent effect from one ring to the other one. PB - Arkat USA Inc. T2 - ARKIVOC - Online Journal of Organic Chemistry T1 - Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones VL - 2009 IS - 13 SP - 227 EP - 240 DO - 10.3998/ark.5550190.0010.d20 ER -
@article{ author = "Valentić, Nataša V. and Vitnik, Željko and Mijin, Dušan and Ušćumlić, Gordana and Todorović, Nina and Juranić, Ivan", year = "2009", abstract = "The C-13 NMR chemical shifts of the C2 carbon atom in the heteroaromatic nuclei of seventeen 5-(3- and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones were determined in deuterated DMSO solution. For quantitative assessment of the substituent effects on the C-13 NMR chemical shifts simple and extended Hammett equations and Swain-Lupton equation were used. The mode of transmission of substituent effects have been discussed in a relation to the geometry of investigated molecules. The geometry data were obtained using semiempirical MNDO-PM6 energy calculations. The observed C-13 NMR substituent chemical shifts were correlated with literature C-13 NMR data for the corresponding 3- and 4-substituted- 2',6'-dimethylazobenzenes and 3- and 4-substituted azobenzenes. A good linear dependence obtained in this way, provided a basis to discuss the influence of the ortho-methyl groups on the degree of coplanarity of azobenzene and pyridone systems, and on the efficiency of transmission of electronic substituent effect from one ring to the other one.", publisher = "Arkat USA Inc.", journal = "ARKIVOC - Online Journal of Organic Chemistry", title = "Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones", volume = "2009", number = "13", pages = "227-240", doi = "10.3998/ark.5550190.0010.d20" }
Valentić, N. V., Vitnik, Ž., Mijin, D., Ušćumlić, G., Todorović, N.,& Juranić, I.. (2009). Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones. in ARKIVOC - Online Journal of Organic Chemistry Arkat USA Inc.., 2009(13), 227-240. https://doi.org/10.3998/ark.5550190.0010.d20
Valentić NV, Vitnik Ž, Mijin D, Ušćumlić G, Todorović N, Juranić I. Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones. in ARKIVOC - Online Journal of Organic Chemistry. 2009;2009(13):227-240. doi:10.3998/ark.5550190.0010.d20 .
Valentić, Nataša V., Vitnik, Željko, Mijin, Dušan, Ušćumlić, Gordana, Todorović, Nina, Juranić, Ivan, "Linear Free Energy Relationships of the C-13 NMR chemical shifts in 5-(3-and 4-substituted arylazo)-4,6-dimethyl-3-cyano-2-pyridones" in ARKIVOC - Online Journal of Organic Chemistry, 2009, no. 13 (2009):227-240, https://doi.org/10.3998/ark.5550190.0010.d20 . .