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Herapathite

Herapathite, or iodoquinine sulfate, is a chemical compound whose crystals are dichroic and thus can be used for polarizing light.

Herapathite
Names
IUPAC name
(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;sulfuric acid;tetratriiodide
Identifiers
  • 7631-46-1
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4912094
ECHA InfoCard 100.028.677
EC Number
  • 231-544-9
  • 6400556
UNII
  • FG2Z310P5U
  • InChI=1S/3C20H24N2O2.4I3.6H2O4S/c3*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;4*1-3-2;6*1-5(2,3)4/h3*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;;;;;6*(H2,1,2,3,4)/q;;;4*-1;;;;;;/t3*13-,14-,19-,20+;;;;;;;;;;/m000........../s1
    Key: RVSIFMMVUGYDOE-RSBHKSPGSA-N
  • COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.I[I-]I.I[I-]I.I[I-]I.I[I-]I
Properties
C60H84I12N6O30S6
Molar mass 3084.56 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

It was discovered in 1852[1] by William Bird Herapath, a Bristol surgeon and chemist. One of his pupils found that adding iodine to the urine of a dog that had been fed quinine produced unusual green crystals. Herapath noticed while studying the crystals under a microscope that they appeared to polarize light.[2]

In the 1930s, Ferdinand Bernauer [de] invented a process to grow single herapathite crystals large enough to be sandwiched between two sheets of glass to create a polarizing filter; these were sold under the Bernotar name by Carl Zeiss. Herapathite can be formed by precipitation by dissolving quinine sulfate in acetic acid and adding iodine tincture.[3]

Herapathite's dichroic properties came to the attention of Sir David Brewster, and were later used by Edwin H. Land in 1929 to construct the first type of Polaroid sheet polarizer. He did this by embedding herapathite crystals in a polymer instead of growing a single large crystal.

Structurally, herapathite consists of quinine (in a cationic doubly-protonated ammonium form), sulfate counterions, and triiodide units, all as a hydrate. They combine as 4C20H26N2O2•3SO4•2I3•6H2O, or sometimes other ratios and higher polyiodides.[4]

References edit

  1. ^ W. B. Herapath (1852). "XXVI. On the optical properties of a newly-discovered salt of quinine, which crystalline substance possesses the power of polarizing a ray of light, like tourmaline, and at certain angles of rotation of depolarizing it, like selenite". Phil. Mag. 3 (17). London: Taylor & Francis: 161–173. doi:10.1080/14786445208646983.
  2. ^ Kahr, Bart; Freudenthal, John; Phillips, Shane; Kaminsky, Werner (2009). "Herapathite". Science. 324 (5933): 1407. Bibcode:2009Sci...324.1407K. doi:10.1126/science.1173605. PMID 19520951. S2CID 220089099.
  3. ^ Gabba, Luigi (1884). Trattato Elementare di Chimica Inorganica ed Organica [Elementary Treatise on Inorganic and Organic Chemistry] (in Italian). Francesco Vallardi. p. 516.
  4. ^ West, C. D. (1937). "Crystallography of herapathite" (PDF). American Mineralogist. 22 (5): 731–735.

Further reading edit

  • Bernauer, F. (1935). "Neue Wege zur Herstellung von Polarisatoren". Forschritte der Mineralogie, Kristallographie und Petrographie Neunzehnter Band.
  • Land, E.H. (1951). "Some aspects on the development of sheet polarizers". Journal of the Optical Society of America. 41 (12): 957–963. doi:10.1364/josa.41.000957.
  • Marks, A. M. (1969). "Electrooptical Characteristics of Dipole Suspensions". Applied Optics. 8 (7): 1397–1412. Bibcode:1969ApOpt...8.1397M. doi:10.1364/AO.8.001397. PMID 20072446.

herapathite, iodoquinine, sulfate, chemical, compound, whose, crystals, dichroic, thus, used, polarizing, light, namesiupac, name, ethenyl, azabicyclo, octan, methoxyquinolin, methanol, sulfuric, acid, tetratriiodideidentifierscas, number, 7631, model, jsmol, . Herapathite or iodoquinine sulfate is a chemical compound whose crystals are dichroic and thus can be used for polarizing light Herapathite NamesIUPAC name R 2S 4S 5R 5 ethenyl 1 azabicyclo 2 2 2 octan 2 yl 6 methoxyquinolin 4 yl methanol sulfuric acid tetratriiodideIdentifiersCAS Number 7631 46 13D model JSmol Interactive imageChemSpider 4912094ECHA InfoCard 100 028 677EC Number 231 544 9PubChem CID 6400556UNII FG2Z310P5UInChI InChI 1S 3C20H24N2O2 4I3 6H2O4S c3 1 3 13 12 22 9 7 14 13 10 19 22 20 23 16 6 8 21 18 5 4 15 24 2 11 17 16 18 4 1 3 2 6 1 5 2 3 4 h3 3 6 8 11 13 14 19 20 23H 1 7 9 10 12H2 2H3 6 H2 1 2 3 4 q 4 1 t3 13 14 19 20 m000 s1Key RVSIFMMVUGYDOE RSBHKSPGSA NSMILES COC1 CC2 C C CN C2C C1 C H C H 3C C H 4CCN3C C H 4C C O COC1 CC2 C C CN C2C C1 C H C H 3C C H 4CCN3C C H 4C C O COC1 CC2 C C CN C2C C1 C H C H 3C C H 4CCN3C C H 4C C O OS O O O OS O O O OS O O O OS O O O OS O O O OS O O O I I I I I I I I I I I IPropertiesChemical formula C 60H 84I 12N 6O 30S 6Molar mass 3084 56 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references It was discovered in 1852 1 by William Bird Herapath a Bristol surgeon and chemist One of his pupils found that adding iodine to the urine of a dog that had been fed quinine produced unusual green crystals Herapath noticed while studying the crystals under a microscope that they appeared to polarize light 2 In the 1930s Ferdinand Bernauer de invented a process to grow single herapathite crystals large enough to be sandwiched between two sheets of glass to create a polarizing filter these were sold under the Bernotar name by Carl Zeiss Herapathite can be formed by precipitation by dissolving quinine sulfate in acetic acid and adding iodine tincture 3 Herapathite s dichroic properties came to the attention of Sir David Brewster and were later used by Edwin H Land in 1929 to construct the first type of Polaroid sheet polarizer He did this by embedding herapathite crystals in a polymer instead of growing a single large crystal Structurally herapathite consists of quinine in a cationic doubly protonated ammonium form sulfate counterions and triiodide units all as a hydrate They combine as 4C20H26N2O2 3SO4 2I3 6H2O or sometimes other ratios and higher polyiodides 4 References edit W B Herapath 1852 XXVI On the optical properties of a newly discovered salt of quinine which crystalline substance possesses the power of polarizing a ray of light like tourmaline and at certain angles of rotation of depolarizing it like selenite Phil Mag 3 17 London Taylor amp Francis 161 173 doi 10 1080 14786445208646983 Kahr Bart Freudenthal John Phillips Shane Kaminsky Werner 2009 Herapathite Science 324 5933 1407 Bibcode 2009Sci 324 1407K doi 10 1126 science 1173605 PMID 19520951 S2CID 220089099 Gabba Luigi 1884 Trattato Elementare di Chimica Inorganica ed Organica Elementary Treatise on Inorganic and Organic Chemistry in Italian Francesco Vallardi p 516 West C D 1937 Crystallography of herapathite PDF American Mineralogist 22 5 731 735 Further reading editBernauer F 1935 Neue Wege zur Herstellung von Polarisatoren Forschritte der Mineralogie Kristallographie und Petrographie Neunzehnter Band Land E H 1951 Some aspects on the development of sheet polarizers Journal of the Optical Society of America 41 12 957 963 doi 10 1364 josa 41 000957 Marks A M 1969 Electrooptical Characteristics of Dipole Suspensions Applied Optics 8 7 1397 1412 Bibcode 1969ApOpt 8 1397M doi 10 1364 AO 8 001397 PMID 20072446 Retrieved from https en wikipedia org w index php title Herapathite amp oldid 1209063548, wikipedia, wiki, book, books, library,

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