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Buthalital and methitural - 5,5-substituted derivatives of 2-thio-barbituric acid forming the same type of hydrogen-bonded chain.

ABSTRACT: The mol-ecule of buthalital, (I) [systematic name: 5-(2-methyl-prop-yl)-5-(prop-2-en-1-yl)-2-sulfanyl-idene-1,3-diazinane-4,6-dione], C₁₁H₁₆N₂O₂S, exhibits a planar pyrimidine ring, whereas the pyrimidine ring of methitural, (II) [systematic name: 5-(1-methyl-but-yl)-5-[2-(methyl-sulfan-yl)eth-yl]-2-sulfanyl-idene-1,3-diazinane-4,6-dione], C₁₂H₂₀N₂O₂S₂, is slightly puckered. (I) and (II) contain the same hydrogen-bonded chain structure in which each mol-ecule is connected, via four N-H?O=C hydrogen bonds, to two other mol-ecules, resulting in a hydrogen-bonded chain displaying a sequence of R₂²(8) rings. The same type of N-H?O=C hydrogen-bonded chain has previously been found in several 5,5-disubstituted derivatives of barbituric acid which are chemically closely related to (I) and (II).

SUBMITTER: Gelbrich T

PROVIDER: S-EPMC5730250 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Buthalital and methitural - 5,5-substituted derivatives of 2-thio-barbituric acid forming the same type of hydrogen-bonded chain.

Gelbrich Thomas T Griesser Ulrich J UJ

Acta crystallographica. Section E, Crystallographic communications 20171121 Pt 12

The mol-ecule of buthalital, (I) [systematic name: 5-(2-methyl-prop-yl)-5-(prop-2-en-1-yl)-2-sulfanyl-idene-1,3-diazinane-4,6-dione], C11H16N2O2S, exhibits a planar pyrimidine ring, whereas the pyrimidine ring of methitural, (II) [systematic name: 5-(1-methyl-but-yl)-5-[2-(methyl-sulfan-yl)eth-yl]-2-sulfanyl-idene-1,3-diazinane-4,6-dione], C12H20N2O2S2, is slightly puckered. (I) and (II) contain th ...[more]

PMID: 29250413

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