Researches on Organic Periodides. I. Periodides of Phenacetin, Methacetin and Triphenin.

Emery, W. O.

doi:10.1021/ja02258a014

Cited by 3 publications

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“…Crystalline (phenacetin) 2-H I5 was prepared by Emery (1914Emery ( , 1916 during an investigation of methods of separating phenacetin, with its desirable medicinal properties, from mixtures which included acetanilide. (Theobromine) 2 • H 2I 8 was first prepared by Jorgensen (1869) and studied by Shaw (1896).…”

Section: Introductionmentioning

confidence: 99%

The crystal structures of the polyiodide salts (phenacetin) ₂ HI ₅ and (theobromine) ₂ H ₂ I ₈

Herbstein

Kapon

1979

Phil. Trans. R. Soc. Lond. A

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The crystal structures of (phenacetin) 2 • H I 5 (triclinic, a — 12.44 A, b — 10.67, c = 5.81, oc = 103.3°, B — 103.7, y — 87.3, P1, Z = 1) and (theobromine) 2 H 2 I 8 (triclinic, a — 14.38 A, b = 14.07, c = 7.75, = 91.2°, B = 100.8, y = 91.0, P1, Z = 2) have been solved by Patterson methods, using intensities measured by Weissenberg diffractometer with graphite-monochromated Mo Ka radiation (2815 and 2827 intensities, R = 8.3 % and 11.1 % respectively). Both structures are polyiodide salts, with alternating cationic (organic) and anionic (polyiodide) layers. In (phenacetin) 2 • H I 5 the organic layers consist of hydrogen-bonded phenacetin 'dimers', with the proton bridging the oxygens of the carbonyl bonds in a short hydrogen bond ( d (O ...O ) = 2.46 (2) A); the polyiodide layers contain zigzag chains of alternating iodine molecules and triiodide ions, with secondary bonds ( d (I...I) = 3.55 A) between these moieties. There is only van der Waals bonding between parallel chains. This substance, bis- (phenacetin) hydrogen iodine triiodide, is a type A basic salt. In (theobromine) 2 • H 2 I 8 the organic layer consists of hydrogen-bonded theobrominium cations and the polyiodide layer of centrosymmetric S-shaped (I 4-16 ) ions, with the arrangement I - 3 •I - 2 •I - 3 •I - 3 •I - 2 •I - 3 ; there is secondary bonding between triiodide and iodine moieties within the hexadecaiodide ions. There are tertiary bonds (d/(I...I) = 3.84 A) between adjacent I 4-16 ions.

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Section: Introductionmentioning

confidence: 99%

The crystal structures of the polyiodide salts (phenacetin) ₂ HI ₅ and (theobromine) ₂ H ₂ I ₈

Herbstein

Kapon

1979

Phil. Trans. R. Soc. Lond. A

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Polarographische Bestimmung des Phenacetins über sein o‐Nitroderivat. 1. Mitt.: Arzneimittelanalysen mittels Polarographie oder Oszillopolarographie

Oelschlaeger

1963

Archiv der Pharmazie

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Zigzag Chains of Alternating Molecules and Triiodide Ions in Crystalline (Phenacetin)2.HI5

Herbstein

Kapon

1972

Nature Physical Science

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Researches on Organic Periodides. I. Periodides of Phenacetin, Methacetin and Triphenin.

Cited by 3 publications

References 0 publications

The crystal structures of the polyiodide salts (phenacetin) ₂ HI ₅ and (theobromine) ₂ H ₂ I ₈

The crystal structures of the polyiodide salts (phenacetin) ₂ HI ₅ and (theobromine) ₂ H ₂ I ₈

Polarographische Bestimmung des Phenacetins über sein o‐Nitroderivat. 1. Mitt.: Arzneimittelanalysen mittels Polarographie oder Oszillopolarographie

Zigzag Chains of Alternating Molecules and Triiodide Ions in Crystalline (Phenacetin)2.HI5

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Researches on Organic Periodides. I. Periodides of Phenacetin, Methacetin and Triphenin.

Cited by 3 publications

References 0 publications

The crystal structures of the polyiodide salts (phenacetin) 2 HI 5 and (theobromine) 2 H 2 I 8

The crystal structures of the polyiodide salts (phenacetin) 2 HI 5 and (theobromine) 2 H 2 I 8

Polarographische Bestimmung des Phenacetins über sein o‐Nitroderivat. 1. Mitt.: Arzneimittelanalysen mittels Polarographie oder Oszillopolarographie

Zigzag Chains of Alternating Molecules and Triiodide Ions in Crystalline (Phenacetin)2.HI5

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The crystal structures of the polyiodide salts (phenacetin) ₂ HI ₅ and (theobromine) ₂ H ₂ I ₈

The crystal structures of the polyiodide salts (phenacetin) ₂ HI ₅ and (theobromine) ₂ H ₂ I ₈