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
2009
Authors
Valentić, NatašaVitnik, Željko
Mijin, Dušan
Ušćumlić, Gordana
Todorović, Nina
Juranić, Ivan
Article (Published version)
Metadata
Show full item recordAbstract
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.
Keywords:
LFER models / arylazo pyridone dyes / substituent effects / azo linking group / MNDO-PM6 and DFT-ab initio calculationsSource:
Arkivoc, 2009, 227-240Publisher:
- Arkat Usa Inc, Gainesville
Funding / projects:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-MESTD-MPN2006-2010-142063)
- Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology (RS-MESTD-MPN2006-2010-142010)
DOI: 10.3998/ark.5550190.0010.d20
ISSN: 1551-7004
WoS: 000277913200020
Scopus: 2-s2.0-77953199233
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Valentić, Nataša AU - Vitnik, Željko AU - Mijin, Dušan AU - Ušćumlić, Gordana AU - Todorović, Nina AU - Juranić, Ivan PY - 2009 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1532 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, Gainesville T2 - Arkivoc 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 EP - 240 SP - 227 DO - 10.3998/ark.5550190.0010.d20 ER -
@article{ author = "Valentić, Nataša 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, Gainesville", journal = "Arkivoc", 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", pages = "240-227", doi = "10.3998/ark.5550190.0010.d20" }
Valentić, N., 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 Arkat Usa Inc, Gainesville., 227-240. https://doi.org/10.3998/ark.5550190.0010.d20
Valentić N, 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. 2009;:227-240. doi:10.3998/ark.5550190.0010.d20 .
Valentić, Nataša, 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 (2009):227-240, https://doi.org/10.3998/ark.5550190.0010.d20 . .