Chemical Shift Tensors in Isomers of Adenine: Relation to
Aromaticity of Purine Rings?

J 2011

Chemical Shift Tensors in Isomers of Adenine: Relation to Aromaticity of Purine Rings?

MALIŇÁKOVÁ, Kateřina, Lucie NOVOSADOVÁ, Matej PIPÍŠKA and Radek MAREK

Basic information

Original name

Chemical Shift Tensors in Isomers of Adenine: Relation to Aromaticity of Purine Rings?

Name in Czech

Tenzory chemického posunu u izomerů adeninu: Vztah k aromaticitě purinových kruhů?

Authors

MALIŇÁKOVÁ, Kateřina (203 Czech Republic, belonging to the institution), Lucie NOVOSADOVÁ (203 Czech Republic, belonging to the institution), Matej PIPÍŠKA (703 Slovakia, belonging to the institution) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution)

Edition

ChemPhysChem, Weinheim, Wiley-VCH, 2011, 1439-4235

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

DOI: 10.1002/cphc.201000657

Impact factor

Impact factor: 3.412

RIV identification code

RIV/00216224:14740/11:00051482

Organization unit

Central European Institute of Technology

DOI

http://dx.doi.org/10.1002/cphc.201000657

UT WoS

000287792300021

Keywords in English

solid-state NMR; density-functional theory; X-ray diffraction; nucleus-independent chemical shift; supramolecular cluster

Abstract

V originále

13C and 15N chemical shift tensors (CST) are measured, calculated, and compared for three N-benzyladenine isomers with an attempt to characterize differences in electron distribution in the purine ring related to the position of the substituent. Furthermore, the aromaticity of the purine rings is evaluated on the basis of nucleus-independent chemical shifts (NICS), and variations among the isomers are discussed. Both parameters indicate significant differences between the electronic properties of the N3-substituted compound and the N7/N9 pair of structures which can be viewed more generally as the reason for the different stabilities of the individual tautomers.

Links

LC06030, research and development project

Name: Biomolekulární centrum

Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular centre

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

Files attached

CPC11_12_379.pdf

Request the author's version of the file

Citovat

MALIŇÁKOVÁ, Kateřina, Lucie NOVOSADOVÁ, Matej PIPÍŠKA and Radek MAREK. Chemical Shift Tensors in Isomers of Adenine: Relation to Aromaticity of Purine Rings? ChemPhysChem. Weinheim: Wiley-VCH, 2011, vol. 12, No 2, p. 379-388. ISSN 1439-4235. Available from: https://dx.doi.org/10.1002/cphc.201000657.

@article{902421,
   author = {Maliňáková, Kateřina and Novosadová, Lucie and Pipíška, Matej and Marek, Radek},
   article_location = {Weinheim},
   article_number = {2},
   doi = {http://dx.doi.org/10.1002/cphc.201000657},
   keywords = {solid-state NMR; density-functional theory; X-ray diffraction; nucleus-independent chemical shift; supramolecular cluster},
   language = {eng},
   issn = {1439-4235},
   journal = {ChemPhysChem},
   title = {Chemical Shift Tensors in Isomers of Adenine: Relation to Aromaticity of Purine Rings?},
   url = {http://dx.doi.org/10.1002/cphc.201000657},
   volume = {12},
   year = {2011}
}

TY  - JOUR
ID  - 902421
AU  - Maliňáková, Kateřina - Novosadová, Lucie - Pipíška, Matej - Marek, Radek
PY  - 2011
TI  - Chemical Shift Tensors in Isomers of Adenine: Relation to Aromaticity of Purine Rings?
JF  - ChemPhysChem
VL  - 12
IS  - 2
SP  - 379-388
EP  - 379-388
PB  - Wiley-VCH
SN  - 14394235
KW  - solid-state NMR
KW  - density-functional theory
KW  - X-ray diffraction
KW  - nucleus-independent chemical shift
KW  - supramolecular cluster
UR  - http://dx.doi.org/10.1002/cphc.201000657
L2  - http://dx.doi.org/10.1002/cphc.201000657
N2  - 13C and 15N chemical shift tensors (CST) are measured, calculated, and compared for three N-benzyladenine isomers with an attempt to characterize differences in electron distribution in the purine ring related to the position of the substituent. Furthermore, the aromaticity of the purine rings is evaluated on the basis of nucleus-independent chemical shifts (NICS), and variations among the isomers are discussed. Both parameters indicate significant differences between the electronic properties of the N3-substituted compound and the N7/N9 pair of structures which can be viewed more generally as the reason for the different stabilities of the individual tautomers.
ER  -

MALIŇÁKOVÁ, Kateřina, Lucie NOVOSADOVÁ, Matej PIPÍŠKA and Radek MAREK. Chemical Shift Tensors in Isomers of Adenine: Relation to Aromaticity of Purine Rings? \textit{ChemPhysChem}. Weinheim: Wiley-VCH, 2011, vol.~12, No~2, p.~379-388. ISSN~1439-4235. Available from: https://dx.doi.org/10.1002/cphc.201000657.

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