Adamantan

Adamantan
Names
	Preferred IUPAC name Adamantane
	Systematic IUPAC name Tricyclo[3.3.1.13,7]decane
Identifiers
CAS Number	281-23-2 ;
3D modél (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:40519 ;
ChEMBL	ChEMBL1614830 ;
ChemSpider	8883 ;
ECHA InfoCard	100.005.457
PubChem <abbr title="<nowiki>Compound ID</nowiki>">CID	9238;
CompTox Dashboard (<abbr title="<nowiki>U.S. Environmental Protection Agency</nowiki>">EPA)	DTXSID5022017 ;
	InChI InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2 Key: ORILYTVJVMAKLC-UHFFFAOYSA-N ; InChI=1/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2 Key: ORILYTVJVMAKLC-UHFFFAOYAG;
	SMILES C1C3CC2CC(CC1C2)C3; C1C2CC3CC1CC(C2)C3;
Properties
Chemical formula	C10H16
Molar mass	136.238 g·mol−1
Appéarance	White to off-white powder
Density	1.08 g/cm3 (20 °C), solid
Melting point	270 °C (518 °F; 543 K) séaled tube
Boiling point	Sublimes
Solubility in water	Poorly soluble
Solubility in other solvents	Soluble in hydrocarbons
Refractive index (nD)	1.568
Structure
Crystal structure	cubic, space group Fm3m
Coordination geometry	4
Dipole moment	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S-phrases (outdated)	24/25/28/37/45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 C₁₀H_16, 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

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-[3.3.1.1^3,7], lain adamantan, tapi turunanana.^[7]

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

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]

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.

Kelimpahan alam

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

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

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

Dumasar kana aturan tata ngaran sistimatis, adamantan disebut trisiklo[3.3.1.1^3,7]dékana. Sanajan kitu, IUPAC ngajak maké ngaran "adamantana".^[1]

Analog adamantan

Loba molekul niron wangun kandang kawas adamantan, kayaning fosfor trioksida P₄O_6, 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

↑ ^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.
↑ 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.
↑ ^a ^b Bagrii, E.I. (1989). Adamantanes: synthesis, properties, applications (in Russian). Nauka. pp. 5–57. ISBN 5-02-001382-X.
↑ Alexander Senning. Elsevier's Dictionary of Chemoetymology. Elsevier, 2006, p. 6 Galat skrip: tidak ada modul tersebut "Catalog lookup link".Galat skrip: tidak ada modul tersebut "check isxn"..
↑ Decker H. (1924). "Versammlung deutscher Naturforscher und Ärzte. Innsbruck, 21–27 September 1924". Angew. Chem. 37 (41): 795. doi:10.1002/ange.19240374102.
↑ 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. Archived 2011-08-09 di Wayback Machine
↑ S. Coffey, S. Rodd (ed.) Chemistry of Carbon Compounds. Vol 2. Part C. Elsevier Publishing Co.: New York. 1969
↑ ^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.
↑ "Über die Synthese des Adamantans". Berichte 74 (10): 1644–1648. 1941. doi:10.1002/cber.19410741004.
↑ "Über eine neue, ergiebigere Darstellung des Adamantans". Berichte 74 (11): 1769–1772. 1941. doi:10.1002/cber.19410741109.
↑ Stetter, H., Bander, O., and Neumann, W., Ber., 89, 1922 (1956).
↑ McKervey, M (1980). "Synthetic approaches to large diamondoid hydrocarbons". Tetrahedron 36 (8): 971–992. doi:10.1016/0040-4020(80)80050-0.
↑ Schleyer, P. von R. (1957). "A Simple Preparation of Adamantane". J. Am. Chem. Soc. 79 (12): 3292–3292. doi:10.1021/ja01569a086.
↑ Citakan:OrgSynth
↑ 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.
↑ 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/.
↑ 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.
↑ "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.
↑ ^a ^b Bagriy EI (1989). "Methods for hydrocarbon adamantane series". Adamantane: Synthesis, properties, application. Moscow: Nauka. pp. 58–123. ISBN 5-02-001382-X.
↑ "Adamantane". Encyclopedia of Chemistry (dalam Russian). Diakses tanggal 2009-12-11.
↑ 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.
↑ 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.
↑ Fischer, Jelena; Baumgartner, Judith; Marschner, Christoph (2005). "Synthesis and Structure of Sila-Adamantane". Science 310 (5749): 825. doi:10.1126/science.1118981. PMID 16272116.

[iupac2013-1] 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.

[lowt-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.

[bagriy_1-3] Bagrii, E.I. (1989). Adamantanes: synthesis, properties, applications (in Russian). Nauka. pp. 5–57. ISBN 5-02-001382-X.

[4] Alexander Senning. Elsevier's Dictionary of Chemoetymology. Elsevier, 2006, p. 6 Galat skrip: tidak ada modul tersebut "Catalog lookup link".Galat skrip: tidak ada modul tersebut "check isxn"..

[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. Archived 2011-08-09 di Wayback Machine

[7] S. Coffey, S. Rodd (ed.) Chemistry of Carbon Compounds. Vol 2. Part C. Elsevier Publishing Co.: New York. 1969

[cr64-8] 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

[app-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.

[landa-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.

[msu_pr-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.

[bagriy_2-19] Bagriy EI (1989). "Methods for hydrocarbon adamantane series". Adamantane: Synthesis, properties, application. Moscow: Nauka. pp. 58–123. ISBN 5-02-001382-X.

[himicheskaya_entsiklopediya-20] "Adamantane". Encyclopedia of Chemistry (dalam Russian). Diakses tanggal 2009-12-11.

[j1-21] 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.

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