Effect of substituents on the C-13 NMR chemical shifts of para-substituted alpha-phenyl-beta-pyridylacrylic acids
Abstract
The C-13 NMR spectra of para-substituted alpha-phenylcinnamic and 3- and 4-pyridylacrylic acids, with a wide range of substituents effects, were determined in deuterated dimethylsulfoxide (DMSO-d(6)). The effect of substituents in both the alpha-phenyl and beta-pyridine groups in these acids is investigated using linear free energy relationships and multiple regression analysis as applied to C-13 NMR chemical shifts of the C-alpha and C-beta of the ethylenic bond and the carboxylic group carbon. Dissection of the alpha-phenyl substituent effects into the inductive and resonance components, using the dual substituent parameter (DSP) method, points to a blend of inductive and resonance effects in the pi-electronic system.
Keywords:
NMR spectroscopy / spectra-structure correlation / para-substituted alpha-phenyl-pyridylacrylic acidsSource:
Journal of Molecular Structure, 1997, 410, 39-41Publisher:
- Elsevier, Amsterdam
DOI: 10.1016/S0022-2860(96)09563-4
ISSN: 0022-2860
WoS: A1997XL06500010
Scopus: 2-s2.0-12644286568
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Jovanović, Bratislav Ž. AU - Misić-Vuković, Milica AU - Drmanić, Saša AU - Canadi, JJ PY - 1997 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/135 AB - The C-13 NMR spectra of para-substituted alpha-phenylcinnamic and 3- and 4-pyridylacrylic acids, with a wide range of substituents effects, were determined in deuterated dimethylsulfoxide (DMSO-d(6)). The effect of substituents in both the alpha-phenyl and beta-pyridine groups in these acids is investigated using linear free energy relationships and multiple regression analysis as applied to C-13 NMR chemical shifts of the C-alpha and C-beta of the ethylenic bond and the carboxylic group carbon. Dissection of the alpha-phenyl substituent effects into the inductive and resonance components, using the dual substituent parameter (DSP) method, points to a blend of inductive and resonance effects in the pi-electronic system. PB - Elsevier, Amsterdam T2 - Journal of Molecular Structure T1 - Effect of substituents on the C-13 NMR chemical shifts of para-substituted alpha-phenyl-beta-pyridylacrylic acids EP - 41 SP - 39 VL - 410 DO - 10.1016/S0022-2860(96)09563-4 ER -
@article{ author = "Jovanović, Bratislav Ž. and Misić-Vuković, Milica and Drmanić, Saša and Canadi, JJ", year = "1997", abstract = "The C-13 NMR spectra of para-substituted alpha-phenylcinnamic and 3- and 4-pyridylacrylic acids, with a wide range of substituents effects, were determined in deuterated dimethylsulfoxide (DMSO-d(6)). The effect of substituents in both the alpha-phenyl and beta-pyridine groups in these acids is investigated using linear free energy relationships and multiple regression analysis as applied to C-13 NMR chemical shifts of the C-alpha and C-beta of the ethylenic bond and the carboxylic group carbon. Dissection of the alpha-phenyl substituent effects into the inductive and resonance components, using the dual substituent parameter (DSP) method, points to a blend of inductive and resonance effects in the pi-electronic system.", publisher = "Elsevier, Amsterdam", journal = "Journal of Molecular Structure", title = "Effect of substituents on the C-13 NMR chemical shifts of para-substituted alpha-phenyl-beta-pyridylacrylic acids", pages = "41-39", volume = "410", doi = "10.1016/S0022-2860(96)09563-4" }
Jovanović, B. Ž., Misić-Vuković, M., Drmanić, S.,& Canadi, J.. (1997). Effect of substituents on the C-13 NMR chemical shifts of para-substituted alpha-phenyl-beta-pyridylacrylic acids. in Journal of Molecular Structure Elsevier, Amsterdam., 410, 39-41. https://doi.org/10.1016/S0022-2860(96)09563-4
Jovanović BŽ, Misić-Vuković M, Drmanić S, Canadi J. Effect of substituents on the C-13 NMR chemical shifts of para-substituted alpha-phenyl-beta-pyridylacrylic acids. in Journal of Molecular Structure. 1997;410:39-41. doi:10.1016/S0022-2860(96)09563-4 .
Jovanović, Bratislav Ž., Misić-Vuković, Milica, Drmanić, Saša, Canadi, JJ, "Effect of substituents on the C-13 NMR chemical shifts of para-substituted alpha-phenyl-beta-pyridylacrylic acids" in Journal of Molecular Structure, 410 (1997):39-41, https://doi.org/10.1016/S0022-2860(96)09563-4 . .