Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(phenyl substituted)pyridine-3-and-2-aldimines
Abstract
C-13 chemical shifts of the azomethine carbon atom for N-(phenyl substituted)pyridine-3-aldimines, 3-Py-CH=N-C6H4-X, and N-(phenyl substituted)pyridine-2-aldimines, 2-Py-CH=N-C6H4-X, having a wide range of substituent effects, were determined in CDCl3 solution. Exceptionally good Hammett correlation of the C-13 NMR chemical shifts of azomethine carbons with electrophilic substituent constants sigma(+) indicate strong resonance interaction of the substituents on the aniline ring with the azomethine carbon atom of the investigated series of imines. The demand for electrons in the investigated systems may be compared to that of the N-benzylidenanilines and N-(phenyl substituted)pyridine-4-aldimines. The mode of transmission of the substituent effects, both inductive and resonance, in all four systems, was discussed.
Keywords:
C-13 NMR spectroscopy / spectra-structure correlations / N-(phenyl substituted)pyridine-3-aldimines / N-(phenyl substituted)pyridine-2-aldiminesSource:
Journal of Molecular Structure, 2002, 642, 1-3, 113-118Publisher:
- Elsevier, Amsterdam
DOI: 10.1016/S0022-2860(02)00403-9
ISSN: 0022-2860
WoS: 000179486200013
Scopus: 2-s2.0-0037021462
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Jovanović, Bratislav Ž. AU - Misić-Vuković, Milica AU - Marinković, Aleksandar AU - Vajs, Vlatka PY - 2002 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/431 AB - C-13 chemical shifts of the azomethine carbon atom for N-(phenyl substituted)pyridine-3-aldimines, 3-Py-CH=N-C6H4-X, and N-(phenyl substituted)pyridine-2-aldimines, 2-Py-CH=N-C6H4-X, having a wide range of substituent effects, were determined in CDCl3 solution. Exceptionally good Hammett correlation of the C-13 NMR chemical shifts of azomethine carbons with electrophilic substituent constants sigma(+) indicate strong resonance interaction of the substituents on the aniline ring with the azomethine carbon atom of the investigated series of imines. The demand for electrons in the investigated systems may be compared to that of the N-benzylidenanilines and N-(phenyl substituted)pyridine-4-aldimines. The mode of transmission of the substituent effects, both inductive and resonance, in all four systems, was discussed. PB - Elsevier, Amsterdam T2 - Journal of Molecular Structure T1 - Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(phenyl substituted)pyridine-3-and-2-aldimines EP - 118 IS - 1-3 SP - 113 VL - 642 DO - 10.1016/S0022-2860(02)00403-9 ER -
@article{ author = "Jovanović, Bratislav Ž. and Misić-Vuković, Milica and Marinković, Aleksandar and Vajs, Vlatka", year = "2002", abstract = "C-13 chemical shifts of the azomethine carbon atom for N-(phenyl substituted)pyridine-3-aldimines, 3-Py-CH=N-C6H4-X, and N-(phenyl substituted)pyridine-2-aldimines, 2-Py-CH=N-C6H4-X, having a wide range of substituent effects, were determined in CDCl3 solution. Exceptionally good Hammett correlation of the C-13 NMR chemical shifts of azomethine carbons with electrophilic substituent constants sigma(+) indicate strong resonance interaction of the substituents on the aniline ring with the azomethine carbon atom of the investigated series of imines. The demand for electrons in the investigated systems may be compared to that of the N-benzylidenanilines and N-(phenyl substituted)pyridine-4-aldimines. The mode of transmission of the substituent effects, both inductive and resonance, in all four systems, was discussed.", publisher = "Elsevier, Amsterdam", journal = "Journal of Molecular Structure", title = "Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(phenyl substituted)pyridine-3-and-2-aldimines", pages = "118-113", number = "1-3", volume = "642", doi = "10.1016/S0022-2860(02)00403-9" }
Jovanović, B. Ž., Misić-Vuković, M., Marinković, A.,& Vajs, V.. (2002). Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(phenyl substituted)pyridine-3-and-2-aldimines. in Journal of Molecular Structure Elsevier, Amsterdam., 642(1-3), 113-118. https://doi.org/10.1016/S0022-2860(02)00403-9
Jovanović BŽ, Misić-Vuković M, Marinković A, Vajs V. Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(phenyl substituted)pyridine-3-and-2-aldimines. in Journal of Molecular Structure. 2002;642(1-3):113-118. doi:10.1016/S0022-2860(02)00403-9 .
Jovanović, Bratislav Ž., Misić-Vuković, Milica, Marinković, Aleksandar, Vajs, Vlatka, "Effect of substituents on the C-13 chemical shifts of the azomethine carbon atom of N-(phenyl substituted)pyridine-3-and-2-aldimines" in Journal of Molecular Structure, 642, no. 1-3 (2002):113-118, https://doi.org/10.1016/S0022-2860(02)00403-9 . .