Adamantan

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Adamantan
Skeletal formula of adamantane
Ball-and-stick model of the adamantane molecule
Small white crystals of adamantane
Names
Preferred IUPAC name
Adamantane[1]
Systematic IUPAC name
Tricyclo[3.3.1.13,7]decane
Identifiers
3D modél (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.457
PubChem <abbr title="<nowiki>Compound ID</nowiki>">CID
CompTox Dashboard (<abbr title="<nowiki>U.S. Environmental Protection Agency</nowiki>">EPA)
Properties
C10H16
Molar mass 136.238 g·mol−1
Appéarance White to off-white powder
Density 1.08 g/cm3 (20 °C),[2] solid
Melting point 270 °C (518 °F; 543 K) séaled tube
Boiling point Sublimes
Poorly soluble
Solubility in other solvents Soluble in hydrocarbons
1.568[3]
Structure
cubic, space group Fm3m
4
0 D
Hazards
Main hazards Flammable
S-phrases (outdated) 24/25/28/37/45
Related compounds
Related compounds:
Memantine

Rimantadine

Amantadine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Adamantan atawa adamantana nyaéta sanyawa kimia kristalin tanwarna anu bauna kawas kamper, boga rumus kimia C10H16, mangrupa sikloalkana sarta diamondoid pangbasajanna. Molekul adamantan diwangun ku gabungan tilu cingcin siklohéksana anu disusun dina konfigurasi "leungeun korsi". Adamantan téh anu pangstabilna ti antara sakabéh isomér anu boga rumus C10H16. Susunan spasial atom karbon dina molekul adamantan sarua jeung dina kristal inten, anu matak éta ogé ngaranna diturunkeun tina Basa Yunani adamantinos (patali jeung baja atawa inten).[4]

Sajarah jeung sintésis[édit | édit sumber]

Taun 1924, H. Decker ngusulkeun ayana adamantan, anu ku anjeunna disebut decaterpene (dékaterpéna).[5]

Sintésis laboratorium munggaran dicoba taun 1924 ku kimiawan Jérman Hans Meerwein ku ngaréaksikeun formaldehida jeung diétil malonat ku ayana piperidin. Lainna ngahasilkeun adamantan, Meerwein kalah meunang 1,3,5,7-tétrakarbométoksibisiklo[3.3.1]nonana-2,6-dion. Sanyawa anu jadi katelah "éster Meerwein" ieu dipaké dina sintésis adamantan jeung turunanana.[6] D. Bottger nyobaan nyieun adamantan maké éster Meerwein salaku prékursor. Hasilna, trisiklo-[3.3.1.13,7], lain adamantan, tapi turunanana.[7]

Kungsi ogé aya nu nyoba nyintésis adamantan maké floroglusinol sarta turunan siklohéksanon, tapi sarua gagal.[8]

Éster Meerwein

Adamantan munggaran disintésis ku Vladimir Prelog taun 1941 ti éster Meerwein.[9][10] Lian ti hasilna anu ukur saeutik 0,16%, carana ogé henteu praktis. Métode ieu dipaké pikeun nyintésis sababaraha turunan adamantan.[8]

Adamantane synthesis by Prelog.png

Métode Prelog diropéa taun 1956. Hasil dekarboksilasi ngalobaan ku ditambahan jalur Heinsdecker (11%) jeung réaksi Hoffman (24%) nepi ka hasilna jadi 6.5%.[11][12] Métode sintésis anu leuwih hadé kapanggih taun 1957 ku Paul von Ragué Schleyer: disiklopentadiéna mimitina dihidrogenasi dibantu katalis (platinum diokida) laju dirobah jadi adamantan maké asam Lewis (aluminium klorida) salaku katalis lianna. Ieu métode ngaronjatkeun hasilna jadi 30–40% sarta nyadiakeun sumber adamantan anu leuwih kahontal; anu laju ngarojong kana karakterisasi adamantan sarta masih dipaké dina prakték di laboratorium.[13][14] Sintésis adamantan ngaronjat jadi 60%[15] jeung 98% maké katalis ultrasora jeung katalis ultrasora jeung asam super.

Adamantane synthesis.png

Kelimpahan alam[édit | édit sumber]

Saméméh disintésis, adamantan diisolasi tina minyak bumi ku kimiawan Céko: S. Landa, V. Machacek jeung M. Mzourek taun 1932.[16][17] Aranjeunna maké distilasi fraksionasi anu misahkeun komponé molekul organik tina minyak bumi dumasar kana titik golakna.

Nepi ka kiwari, sumber alami adamantan masih ngandelkeun minyak bumi; kandunganana antara 0,0001% nepi ka 0,03%, saeutik teuing pikeun produksi komérsil mah.[18][19]

Pasipatan pisik[édit | édit sumber]

Adamantan murni tanwarna, kristalin padet nu bauna kawas kamper. Henteu leyur dina cai, tapi leyur dina pelarut organik nonpolar.[20] Salaku hidrokarbon, adamantan boga titik léé anu kaasup luhur (270 °C), bandingkeun jeung séjén hidrokarbon anu beurat molekulna sapantar: kampéna (45 °C), limonéna (-74 °C), osiména (50 °C), terpinéna (60 °C), twistana (164 °C), atawa hidrokarbon liniér C10H22 dékana (-28 °C). Ahéngna, adamantan kalah nyublim lalaunan dina hawa kamar.[21] Adamantan bisa disuling maké saab cai.[19]

Wangun[édit | édit sumber]

Adamantane molecular parameters.png

Molekul adamantan diwangun ku tilu cingcin siklohéksana anu ngahiji dina konformasi korsi. Paraméter molekular dicindekkeun maké difraksi éléktron jeung kristalografi sinar-X. Panjang beungkeut karbon-karbonna 1,54 Å, ampir sarua jeung dina inten, anapon jarak karbon-hidrogénna 1,112 Å.[3]

Tata ngaran[édit | édit sumber]

Dumasar kana aturan tata ngaran sistimatis, adamantan disebut trisiklo[3.3.1.13,7]dékana. Sanajan kitu, IUPAC ngajak maké ngaran "adamantana".[1]

Adamantane numbering.svg

Analog adamantan[édit | édit sumber]

Loba molekul niron wangun kandang kawas adamantan, kayaning fosfor trioksida P4O6, arsétrioksida aaAsO6 fosfor pentoxikse a 4O1 = (PO) 4O6 fosfor pentasulfide a 4S1 = (PS)4S6 sarta héksamétilénatétramina C6N4H12 = N4(CH2)6.[22] Anu sohor di antarana tétramétilénadisulfotétramina, atawa nu katelah "tétramina", hiji rodéntisida anu geus dicaram di loba nagara ku sabab bahya ogk pieeun manusa Analog silikon tina adamantan, sila-adamantan, disintésis taun 2005.[23]

Rujukan[édit | édit sumber]

  1. a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 169. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The retained names adamantane and cubane are used in general nomenclature and as preferred IUPAC names.
  2. Windsor, C G; Saunderson, D H; Sherwood, J N; Taylor, D; Pawley, G S (1978). "Lattice dynamics of adamantane in the disordered phase". Journal of Physics C: Solid State Physics 11 (9): 1741–1759. Bibcode 1978JPhC...11.1741W. doi:10.1088/0022-3719/11/9/013. 
  3. a b Bagrii, E.I. (1989). Adamantanes: synthesis, properties, applications (in Russian). Nauka. pp. 5–57. ISBN 5-02-001382-X.Page Modul:Citation/CS1/styles.css has no content.
  4. Alexander Senning. Elsevier's Dictionary of Chemoetymology. Elsevier, 2006, p. 6 Citakan:Catalog lookup linkGalat skrip: tidak ada modul tersebut..
  5. Decker H. (1924). "Versammlung deutscher Naturforscher und Ärzte. Innsbruck, 21–27 September 1924". Angew. Chem. 37 (41): 795. doi:10.1002/ange.19240374102. 
  6. Radcliffe, Marc D.; Gutierrez, Alberto; Blount, John F.; Mislow, Kurt (1984). "Structure of Meerwein's ester and of its benzene inclusion compound". Journal of the American Chemical Society 106 (3): 682–687. doi:10.1021/ja00315a037. Diarsipkan on 2011-08-09. Kesalahan: If you specify |archivedate=, you must also specify |archiveurl=. http://www.oci.uzh.ch/efiles/OCVII/ja00315a037.pdf. Diakses pada 2010-05-26. 
  7. S. Coffey, S. Rodd (ed.) Chemistry of Carbon Compounds. Vol 2. Part C. Elsevier Publishing Co.: New York. 1969
  8. a b Fort, Raymond C. Jr.; Schleyers, Paul Von R. (1964). "Adamantane: Consequences of Diamondoid Structure". Chem. Rev. 64 (3): 277–300. doi:10.1021/cr60229a004. 
  9. "Über die Synthese des Adamantans". Berichte 74 (10): 1644–1648. 1941. doi:10.1002/cber.19410741004. 
  10. "Über eine neue, ergiebigere Darstellung des Adamantans". Berichte 74 (11): 1769–1772. 1941. doi:10.1002/cber.19410741109. 
  11. Stetter, H., Bander, O., and Neumann, W., Ber., 89, 1922 (1956).
  12. McKervey, M (1980). "Synthetic approaches to large diamondoid hydrocarbons". Tetrahedron 36 (8): 971–992. doi:10.1016/0040-4020(80)80050-0. 
  13. Schleyer, P. von R. (1957). "A Simple Preparation of Adamantane". J. Am. Chem. Soc. 79 (12): 3292–3292. doi:10.1021/ja01569a086. 
  14. Citakan:OrgSynth
  15. Mansoori, G. Ali (2007). Molecular building blocks for nanotechnology: from diamondoids to nanoscale materials and applications. Springer. pp. 48–55. ISBN 0-387-39937-2. 
  16. Landa, S.; Machácek, V. (1933). "Sur l'adamantane, nouvel hydrocarbure extrait de naphte.". Collect. Czech. Chem. Commun. 5: 1–5. doi:10.1135/cccc19330001. http://cccc.uochb.cas.cz/5/0/0001/. 
  17. Landa, S.; Machacek, V.; Mzourek, M.; Landa, M. (1933), "Title unknown", Chim Ind. Spec. Publ. Vol. 506 (Abstracts of the 12th Conference of Industrial Chemistry, Prague, Sept. 1932); Chem. Abstr. 1933. Vol. 27. P. 5949. 
  18. "Synthesis of adamantane" (dalam Russian). Diakses tanggal 2009-12-11.  Special practical problem for the students of IV year. Department of Petroleum Chemistry and Organic Catalysis MSU.
  19. a b Bagriy EI (1989). "Methods for hydrocarbon adamantane series". Adamantane: Synthesis, properties, application. Moscow: Nauka. pp. 58–123. ISBN 5-02-001382-X. 
  20. "Adamantane". Encyclopedia of Chemistry (dalam Russian). Diakses tanggal 2009-12-11. 
  21. Vijayakumar, V. (2001). "Pressure induced phase transitions and equation of state of adamantane". J. Phys.: Condens. Matter 13 (9): 1961–1972. Bibcode 2001JPCM...13.1961V. doi:10.1088/0953-8984/13/9/318. 
  22. Vitall, J. J. (1996). "The Chemistry of Inorganic and Organometallic Compounds with Adamantane-Like Structures". Polyhedron 15 (10): 1585–1642. doi:10.1016/0277-5387(95)00340-1. 
  23. Fischer, Jelena; Baumgartner, Judith; Marschner, Christoph (2005). "Synthesis and Structure of Sila-Adamantane". Science 310 (5749): 825. doi:10.1126/science.1118981. PMID 16272116.