| STANDARA, Stanislav, Kateřina BOUZKOVÁ, Michal STRAKA, Zuzana ZACHAROVÁ, Michal HOCEK, Jaromír MAREK a Radek MAREK. Interpretation of substituent effects on 13C and 15N NMR chemical shifts in 6-substituted purines. Physical Chemistry Chemical Physics. Royal Society of Chemistry, 2011, roč. 13, č. 35, s. 15854-15864. ISSN 1463-9076. Dostupné z: https://dx.doi.org/10.1039/c1cp20680j. |
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@article{947535,
author = {Standara, Stanislav and Bouzková, Kateřina and Straka, Michal and Zacharová, Zuzana and Hocek, Michal and Marek, Jaromír and Marek, Radek},
article_number = {35},
doi = {http://dx.doi.org/10.1039/c1cp20680j},
keywords = {Purine; Nuclear magnetic shielding; Localized molecular orbitals; Conformational dependence},
language = {eng},
issn = {1463-9076},
journal = {Physical Chemistry Chemical Physics},
title = {Interpretation of substituent effects on 13C and 15N NMR chemical shifts in 6-substituted purines},
url = {http://dx.doi.org/10.1039/c1cp20680j},
volume = {13},
year = {2011}
}
TY - JOUR
ID - 947535
AU - Standara, Stanislav - Bouzková, Kateřina - Straka, Michal - Zacharová, Zuzana - Hocek, Michal - Marek, Jaromír - Marek, Radek
PY - 2011
TI - Interpretation of substituent effects on 13C and 15N NMR chemical shifts in 6-substituted purines
JF - Physical Chemistry Chemical Physics
VL - 13
IS - 35
SP - 15854-15864
EP - 15854-15864
PB - Royal Society of Chemistry
SN - 14639076
KW - Purine
KW - Nuclear magnetic shielding
KW - Localized molecular orbitals
KW - Conformational dependence
UR - http://dx.doi.org/10.1039/c1cp20680j
L2 - http://dx.doi.org/10.1039/c1cp20680j
N2 - The present work aims to analyze the effects of substituents on the electron distribution in the purine core as reflected by NMR chemical shifts. We collected a comprehensive set of experimental NMR data for a variety of 6-substituted purines and determined the molecular and crystal structures of three derivatives by X-ray diffraction. The density-functional methods have been employed to enable understanding of the substituent-induced changes in the NMR chemical shifts of the atoms in the purine skeleton. Analyses of the nuclear shielding using localized molecular orbitals (LMOs) were used to break down the values of the isotropic 13C and 15N NMR chemical shifts and the chemical shift tensors into the contributions of the individual LMOs. The experimental and calculated trends in the chemical shift of the N-3 atom correlate nicely with the Hammett constants and the calculated natural charges on N-3, whereas the contributions of the LMOs to the N-1 and C-6 chemical shifts are found to be more complex.
ER -
STANDARA, Stanislav, Kateřina BOUZKOVÁ, Michal STRAKA, Zuzana ZACHAROVÁ, Michal HOCEK, Jaromír MAREK a Radek MAREK. Interpretation of substituent effects on 13C and 15N NMR chemical shifts in 6-substituted purines. \textit{Physical Chemistry Chemical Physics}. Royal Society of Chemistry, 2011, roč.~13, č.~35, s.~15854-15864. ISSN~1463-9076. Dostupné z: https://dx.doi.org/10.1039/c1cp20680j.
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