STANDARA, Stanislav, Kateřina BOUZKOVÁ, Michal STRAKA, Zuzana ZACHAROVÁ, Michal HOCEK, Jaromír MAREK and 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, vol. 13, No 35, p. 15854-15864. ISSN 1463-9076. doi:10.1039/c1cp20680j.
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Basic information
Original name Interpretation of substituent effects on 13C and 15N NMR chemical shifts in 6-substituted purines
Authors STANDARA, Stanislav (203 Czech Republic, belonging to the institution), Kateřina BOUZKOVÁ (203 Czech Republic, belonging to the institution), Michal STRAKA (203 Czech Republic), Zuzana ZACHAROVÁ (703 Slovakia, belonging to the institution), Michal HOCEK (203 Czech Republic), Jaromír MAREK (203 Czech Republic, belonging to the institution) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution).
Edition Physical Chemistry Chemical Physics, Royal Society of Chemistry, 2011, 1463-9076.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10403 Physical chemistry
Country of publisher United Kingdom of Great Britain and Northern Ireland
Confidentiality degree is not subject to a state or trade secret
WWW DOI: 10.1039/c1cp20680j
Impact factor Impact factor: 3.573
RIV identification code RIV/00216224:14740/11:00052846
Organization unit Central European Institute of Technology
Doi http://dx.doi.org/10.1039/c1cp20680j
UT WoS 000294167700016
Keywords in English Purine; Nuclear magnetic shielding; Localized molecular orbitals; Conformational dependence
Tags ok, rivok
Tags International impact, Reviewed
Changed by Changed by: Olga Křížová, učo 56639. Changed: 18. 6. 2013 08:23.
Abstract
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.
Links
ED1.1.00/02.0068, research and development projectName: CEITEC - central european institute of technology
LC06030, research and development projectName: Biomolekulární centrum
Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular centre
MSM0021622410, plan (intention)Name: Fyzikální a chemické vlastnosti pokročilých materiálů a struktur
Investor: Ministry of Education, Youth and Sports of the CR, Physical and chemical properties of advanced materials and structures
MSM0021622413, plan (intention)Name: Proteiny v metabolismu a při interakci organismů s prostředím
Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment
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