The studies of tautomerism in 6-mercaptopurine derivatives by 1H-13C, 1H-15N NMR and 13C, 15N CP/MAS-experimental and quantum chemical approach

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F06%3A00025547" target="_blank" >RIV/00216224:14310/06:00025547 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

The studies of tautomerism in 6-mercaptopurine derivatives by 1H-13C, 1H-15N NMR and 13C, 15N CP/MAS-experimental and quantum chemical approach

Original language description

Tautomerism in 6-mercaptopurine (6mpH), 2,6-dimercaptopurine (2,6dmp) and 6-mercaptopurine-9-riboside (6mp-9rb) was studied in the solution with 2D NMR methods-1H-13C HMBC and 1H-15N HMQC. The 15N NMR signals were assigned and the distribution of mobileprotons proposed on the basis of 13C, 15N chemical shifts and JHC, JHN coupling constants, determined with HECADE. These heterocycles appear in DMSO-d6 as the thionic species with predominance of the following tautomers: N(1)H, N(7)H for 6mpH; N(1)H, N(3)H, N(7)H for 2,6dmp; N(1)H for 6mp-9rb. Quantum-chemical NMR calculations by GIAO method(RHF/6-31G**//B3LYP/6-31G**) allowed to evaluate the ratios of N(7)H, N(9): N(7), N(9)H tautomeric forms as ca. 3:1 for 6mpH and nearly 10:0 for 2,6dmp. The 13C and15N CPMAS spectra were measured for solid 6mpHH2O, anhydrous 6mpH, 2,6dmp and 6-mercaptopurinium chloride (6mpH2Cl), confirming the thionic character of all compounds. The 15N chemical shifts in the solid phase were calculated (B3LYP/631G

Czech name

Studium tautomerie derivátů 6-merkaptopurinu pomocí 1H-13C, 1H-15N a 13C, 15N CP/MAS experimentálního a kvantově chemického přístupu

Czech description

Deriváty 6-merkaptopurinu byly studovány v roztoku a v pevném stavu pomocí NMR spektroskopie, rentgenové difrakce a kvantově chemických výpočtů.

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CF - Physical chemistry and theoretical chemistry

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2006

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

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Volume of the periodical

785

Issue of the periodical within the volume

1

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

11

Pages from-to

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UT code for WoS article

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EID of the result in the Scopus database

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