TY - JOUR
T1 - Tautomerism and ionisation processes in 6-methylthio-2-oxopurines
AU - Lichtenberg, Dov
AU - Bergmann, Felix
AU - Neiman, Zohar
PY - 1973
Y1 - 1973
N2 - 6-Methylthio-2-oxopurine (1) is present in aqueous solution mainly as the 3.7-di-NH tautomer. This supports the general assumption that purines avoid 3,9-disubstituted structures. Anion formation in structure (1) takes place first at the 7- and then at the 3-position. Cations bearing a 1-methyl group are unstable, undergoing hydrolysis, even at pH 4.5. to the corresponding xanthines. In the n.m.r. spectra of the 1-methyl derivatives of (1), steric interference causes a marked downfield shift of the 6-SMe signal.
AB - 6-Methylthio-2-oxopurine (1) is present in aqueous solution mainly as the 3.7-di-NH tautomer. This supports the general assumption that purines avoid 3,9-disubstituted structures. Anion formation in structure (1) takes place first at the 7- and then at the 3-position. Cations bearing a 1-methyl group are unstable, undergoing hydrolysis, even at pH 4.5. to the corresponding xanthines. In the n.m.r. spectra of the 1-methyl derivatives of (1), steric interference causes a marked downfield shift of the 6-SMe signal.
UR - https://www.scopus.com/pages/publications/0015777339
U2 - 10.1039/p19730002445
DO - 10.1039/p19730002445
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C2 - 4797712
AN - SCOPUS:0015777339
SN - 1472-7781
SP - 2445
EP - 2448
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -