Tautomerism and ionisation of purin-8-one and its N-methyl derivatives

Dov Lichtenberg; Felix Bergmann; Miriam Rabat; Zohar Neiman

doi:10.1039/P19720002950

Tautomerism and ionisation of purin-8-one and its N-methyl derivatives

Dov Lichtenberg
, Felix Bergmann^*
, Miriam Rabat
, Zohar Neiman

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

U.v. and n.m.r. spectra show that in aqueous solutions purin-8-one is present predominantly as the 7H,9H-tautomer. Anion formation takes place preferentially at N-9. Protonation of purin-8-one and its 7- and 9-methyl derivatives occurs at N-1 and causes splitting of the 6-H and 2-H n.m.r. signals. In purin-8-one and its N-methyl derivatives, the 2-H is more deshielded than the 6-H; the reverse is the case for purine itself.

Original language	English
Pages (from-to)	2950-2953
Number of pages	4
Journal	Journal of the Chemical Society, Perkin Transactions 1
DOIs	https://doi.org/10.1039/P19720002950
State	Published - 1972

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title = "Tautomerism and ionisation of purin-8-one and its N-methyl derivatives",

abstract = "U.v. and n.m.r. spectra show that in aqueous solutions purin-8-one is present predominantly as the 7H,9H-tautomer. Anion formation takes place preferentially at N-9. Protonation of purin-8-one and its 7- and 9-methyl derivatives occurs at N-1 and causes splitting of the 6-H and 2-H n.m.r. signals. In purin-8-one and its N-methyl derivatives, the 2-H is more deshielded than the 6-H; the reverse is the case for purine itself.",

author = "Dov Lichtenberg and Felix Bergmann and Miriam Rabat and Zohar Neiman",

year = "1972",

doi = "10.1039/P19720002950",

language = "אנגלית",

pages = "2950--2953",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Royal Society of Chemistry",

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T1 - Tautomerism and ionisation of purin-8-one and its N-methyl derivatives

AU - Lichtenberg, Dov

AU - Bergmann, Felix

AU - Rabat, Miriam

AU - Neiman, Zohar

PY - 1972

Y1 - 1972

N2 - U.v. and n.m.r. spectra show that in aqueous solutions purin-8-one is present predominantly as the 7H,9H-tautomer. Anion formation takes place preferentially at N-9. Protonation of purin-8-one and its 7- and 9-methyl derivatives occurs at N-1 and causes splitting of the 6-H and 2-H n.m.r. signals. In purin-8-one and its N-methyl derivatives, the 2-H is more deshielded than the 6-H; the reverse is the case for purine itself.

AB - U.v. and n.m.r. spectra show that in aqueous solutions purin-8-one is present predominantly as the 7H,9H-tautomer. Anion formation takes place preferentially at N-9. Protonation of purin-8-one and its 7- and 9-methyl derivatives occurs at N-1 and causes splitting of the 6-H and 2-H n.m.r. signals. In purin-8-one and its N-methyl derivatives, the 2-H is more deshielded than the 6-H; the reverse is the case for purine itself.

UR - https://www.scopus.com/pages/publications/37049139481

U2 - 10.1039/P19720002950

DO - 10.1039/P19720002950

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AN - SCOPUS:37049139481

SN - 1472-7781

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EP - 2953

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

ER -

Tautomerism and ionisation of purin-8-one and its N-methyl derivatives

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