Témbongkeun sumber pikeun Adamantan

{| class="infobox bordered" style="border-collapse:collapse; width:22em; text-align:left; ;"
|+ id="5" style="text-align:center;" |Adamantan 
| colspan="2" style="text-align:center; padding:2px;" |[[File:Adamantane_acsv.svg|al=Skeletal formula of adamantane|160x160px|Skeletal formula of adamantane]]
|-
| colspan="2" style="text-align:center; padding:2px;" |[[File:Adamantane_3D_ball.png|al=Ball-and-stick model of the adamantane molecule|163x163px|Ball-and-stick model of the adamantane molecule]]
|-
| colspan="2" style="text-align:center; padding:2px;" |[[File:Adamantane.JPG|al=Small white crystals of adamantane|220x220px|Small white crystals of adamantane]]
|-
! colspan="2" style="background: #f8eaba; text-align: center;" |Names
|-
| colspan="2" style="text-align:left;" |[[Preferred IUPAC name]]
<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="padding:0.1em 0;line-height:1.2em;">Adamantane<ref name="iupac2013"><cite class="citation book">''Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)''. Cambridge: [[Royal Society of Chemistry|The Royal Society of Chemistry]]. 2014. p.&nbsp;169. [[Digital object identifier|doi]]:[[doi:10.1039/9781849733069-FP001|10.1039/9781849733069-FP001]]. [[International Standard Book Number|ISBN]]&nbsp;[[Special:BookSources/978-0-85404-182-4|<bdi>978-0-85404-182-4</bdi>]]. <q>The retained names adamantane and cubane are used in general nomenclature and as preferred IUPAC names.</q></cite></ref></div></div>
|-
| colspan="2" style="text-align:left;" |[[Chemical nomenclature#Systematic name|Systematic IUPAC name]]
<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="padding:0.1em 0;line-height:1.2em;">Tricyclo[3.3.1.1<sup>3,7</sup>]decane</div></div>
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! colspan="2" style="background: #f8eaba; text-align: center;" |Identifiers
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|<div style="padding:0.1em 0;line-height:1.2em;">[[CAS Registry Number|CAS Number]]</div>
|<div class="plainlist">
* <span title="www.commonchemistry.org">[http://www.commonchemistry.org/ChemicalDetail.aspx?ref=281-23-2 281-23-2]</span><sup>&nbsp;[[File:Yes_check.svg|pra=|alt=&#9745;|7x7px]]<span style="display:none">Y</span></sup>
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|<div style="padding:0.1em 0;line-height:1.2em;">3D modél ([[JSmol]])</div>
|<div class="plainlist">
* <span title="chemapps.stolaf.edu (3D interactive model)">[https://chemapps.stolaf.edu/jmol/jmol.php?model=C1C3CC2CC%28CC1C2%29C3 Interactive image]</span>
* <span title="chemapps.stolaf.edu (3D interactive model)">[https://chemapps.stolaf.edu/jmol/jmol.php?model=C1C2CC3CC1CC%28C2%29C3 Interactive image]</span>
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|[[ChEBI]]
|<div class="plainlist">
* <span title="www.ebi.ac.uk">[https://www.ebi.ac.uk/chebi/searchId.do?chebiId=40519 CHEBI:40519]</span><sup>&nbsp;[[File:Yes_check.svg|pra=|alt=&#9745;|7x7px]]<span style="display:none">Y</span></sup>
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|[[ChEMBL]]
|<div class="plainlist">
* <span title="www.ebi.ac.uk">[https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL1614830 ChEMBL1614830]</span><sup>&nbsp;[[File:X_mark.svg|pra=|alt=&#9746;|8x8px]]<span style="display:none">N</span></sup>
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|[[ChemSpider]]
|<div class="plainlist">
* <span title="www.chemspider.com">[http://www.chemspider.com/Chemical-Structure.8883.html 8883]</span><sup>&nbsp;[[File:Yes_check.svg|pra=|alt=&#9745;|7x7px]]<span style="display:none">Y</span></sup>
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|[[ECHA InfoCard|<span title="echa.europa.eu">ECHA InfoCard</span>]]
|[https://echa.europa.eu/substance-information/-/substanceinfo/100.005.457 100.005.457]
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|<div style="padding:0.1em 0;line-height:1.2em;">[[PubChem]] <abbr title="<nowiki&gt;Compound ID</nowiki&gt;">CID</abbr></div>
|<div class="plainlist">
* <span title="pubchem.ncbi.nlm.nih.gov">[https://pubchem.ncbi.nlm.nih.gov/compound/9238 9238]</span>
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|<div style="padding:0.1em 0;line-height:1.2em;">[[CompTox Chemicals Dashboard|CompTox Dashboard]] <span style="font-weight:normal">(<abbr title="<nowiki&gt;U.S. Environmental Protection Agency</nowiki&gt;">EPA</abbr>)</span></div>
|<div class="plainlist">
* <span title="comptox.epa.gov">[https://comptox.epa.gov/dashboard/DTXSID5022017 DTXSID5022017] [[File:Blue_pencil.svg|pra=https://www.wikidata.org/wiki/Q351461#P3117|al=Edit this at Wikidata|atek|nirbing|10x10px|Edit this at Wikidata]]</span>
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| colspan="2" |<div class="NavFrame collapsed" style="border: none; padding: 0;">
<div class="NavHead" style="font-size: 105%; text-align:left; font-weight:normal; background:transparent;">[[International Chemical Identifier|InChI]]</div>

* <div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:11px; line-height:120%;">InChI=1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2<sup>&nbsp;[[File:Yes_check.svg|pra=|alt=&#9745;|7x7px]]<span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:11px; line-height:120%;">Key:&nbsp;ORILYTVJVMAKLC-UHFFFAOYSA-N<sup>&nbsp;[[File:Yes_check.svg|pra=|alt=&#9745;|7x7px]]<span style="display:none">Y</span></sup></div></div>
* <div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:11px; line-height:120%;">InChI=1/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:11px; line-height:120%;">Key:&nbsp;ORILYTVJVMAKLC-UHFFFAOYAG</div></div>
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| colspan="2" |<div class="NavFrame collapsed" style="border: none; padding: 0;">
<div class="NavHead" style="font-size: 105%; text-align:left; font-weight:normal; background:transparent;">[[Simplified molecular-input line-entry system|SMILES]]</div>

* <div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:11px; line-height:120%;">C1C3CC2CC(CC1C2)C3</div>
* <div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:11px; line-height:120%;">C1C2CC3CC1CC(C2)C3</div>
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|-
! colspan="2" style="background: #f8eaba; text-align: center;" |Properties
|-
|<div style="padding:0.1em 0;line-height:1.2em;">[[Chemical formula]]</div>
|<span title="Carbon">C</span><sub>10</sub><span title="Hydrogen">H</span><sub>16</sub>
|-
|[[Molar mass]]
|<span class="nowrap">136.238</span>&nbsp;g·mol<sup>−1</sup>  
|-
|Appéarance
|White to off-white powder
|-
|[[Density]]
|1.08 g/cm<sup>3</sup> (20&nbsp;°C),<ref name="lowt">{{cite journal|last1=Windsor|first1=C G|last2=Saunderson|first2=D H|last3=Sherwood|first3=J N|last4=Taylor|first4=D|last5=Pawley|first5=G S|year=1978|title=Lattice dynamics of adamantane in the disordered phase|journal=Journal of Physics C: Solid State Physics|volume=11|issue=9|pages=1741–1759|bibcode=1978JPhC...11.1741W|doi=10.1088/0022-3719/11/9/013}}</ref> solid
|-
|[[Melting point]]
| 270&nbsp;°C (518&nbsp;°F; 543&nbsp;K) séaled tube
|-
|[[Boiling point]]
|Sublimes  
|-
|<div style="padding:0.1em 0;line-height:1.2em;">[[Aqueous solution|Solubility in water]]</div>
|Poorly soluble
|-
|[[Solubility]] in other solvents
|Soluble in hydrocarbons
|-
|<div style="padding:0.1em 0;line-height:1.2em;">[[Refractive index]] (''n''<sub>D</sub>)</div>
|1.568<ref name="bagriy_1"><cite class="citation book">Bagrii, E.I. (1989). [https://books.google.com/books?id=8RA2AAAAIAAJ&dq=isbn=502001382X ''Adamantanes: synthesis, properties, applications''] (in Russian). Nauka. pp.&nbsp;5–57. [[International Standard Book Number|ISBN]]&nbsp;[[Special:BookSources/5-02-001382-X|<bdi>5-02-001382-X</bdi>]].</cite><templatestyles src="Module:Citation/CS1/styles.css"></templatestyles></ref>
|-
! colspan="2" style="background: #f8eaba; text-align: center;" |Structure
|-
|<div style="padding:0.1em 0;line-height:1.2em;">[[Crystal structure]]</div>
|[[Cubic crystal system|cubic]], [[space group]] Fm3m
|-
|<div style="padding:0.1em 0;line-height:1.2em;">[[Coordination geometry]]</div>
|4
|-
|<div style="padding:0.1em 0;line-height:1.2em;">[[Dipole#Molecular dipoles|Dipole moment]]</div>
|0 [[Debye|D]]
|-
! colspan="2" style="background: #f8eaba; text-align: center;" |Hazards
|-
|Main [[Worker safety and health|hazards]]
|Flammable
|-
|[[List of S-phrases|S-phrases]] <span style="background:moccasin; line-height:85%;">[[CLP Regulation#Implementation|<small title="Per CLP Regulation, outdated per 1 June 2017. Replaced by GHS data">''(outdated)''</small>]]</span>
|24/25/28/37/45
|-
! colspan="2" style="background: #f8eaba; text-align: center;" |Related compounds
|-
|<div style="padding:0.1em 0;line-height:1.2em;">Related compounds:</div>
|[[Memantine]]<br /><br />[[Rimantadine]]<br /><br /> [[Amantadine]]
|-
| colspan="2" style="text-align:left; background:#f8eaba;" |<div style="margin:0 auto; text-align:left;"><div style="padding:0.1em 0;line-height:1.2em;">Except where otherwise noted, data are given for materials in their [[standard state]] (at 25&nbsp;°C [77&nbsp;°F], 100&nbsp;kPa).</div></div>
|- style="background:#f8eaba; border-top:2px solid transparent;"
| colspan="2" style="text-align:center;" |[[File:X_mark.svg|pra=|alt=&#9746;|14x14px]]<span style="display:none">N</span>&nbsp;<span class="reflink plainlinks nourlexpansion">[//en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477241894&page2=Adamantane verify]</span>&nbsp;([[wikipedia:WikiProject Chemicals/Chembox validation|what is]]&nbsp;<sup>[[File:Yes_check.svg|pra=|alt=&#9745;|7x7px]]<span style="display:none">Y</span>[[File:X_mark.svg|pra=|alt=&#9746;|8x8px]]<span style="display:none">N</span></sup>&nbsp;?)
|- style="background:#f8eaba; border-top:2px solid transparent;"
| colspan="2" style="text-align:center;" |[[wikipedia:Chemical infobox#References|Infobox&nbsp;references]]
|- style="background:#f8eaba;"
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'''Adamantan''' atawa '''adamantana''' nyaéta [[sanyawa kimia]] [[kristal]]in tanwarna anu bauna kawas [[kamper]], boga [[rumus kimia]] C<sub>10</sub>H<sub>16,</sub> 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 C<sub>10</sub>H<sub>16</sub>. Susunan spasial [[atom]] [[karbon]] dina molekul adamantan sarua jeung dina kristal [[Berlian|inten]], anu matak éta ogé ngaranna diturunkeun tina [[Basa Yunani]] ''adamantinos'' (patali jeung baja atawa [[Berlian|inten]]).<ref>Alexander Senning. [https://books.google.com/books?id=Fl4sdCYrq3cC&pg=PA6 ''Elsevier's Dictionary of Chemoetymology'']. Elsevier, '''2006''', p. 6 {{ISBN|0-444-52239-5}}.</ref>

== Sajarah jeung sintésis ==
Taun [[1924]], H. Decker ngusulkeun ayana adamantan, anu ku anjeunna disebut '''''decaterpene''''' ('''dékaterpéna''').<ref>{{Cite journal|last=Decker H.|year=1924|title=Versammlung deutscher Naturforscher und Ärzte. Innsbruck, 21–27 September 1924|journal=Angew. Chem.|volume=37|issue=41|pages=795|doi=10.1002/ange.19240374102}}</ref>

Sintésis laboratorium munggaran dicoba taun [[1924]] ku [[kimia]]wan [[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.<ref>{{Cite journal|last=Radcliffe|first=Marc D.|last2=Gutierrez|first2=Alberto|last3=Blount|first3=John F.|last4=Mislow|first4=Kurt|author-link4=Kurt Mislow|year=1984|title=Structure of Meerwein's ester and of its benzene inclusion compound|url=http://www.oci.uzh.ch/efiles/OCVII/ja00315a037.pdf|dead-url=yes|journal=Journal of the American Chemical Society|volume=106|issue=3|pages=682–687|doi=10.1021/ja00315a037|archive-url=https://web.archive.org/web/20110809064625/http://www.oci.uzh.ch/efiles/OCVII/ja00315a037.pdf|archive-date=2011-08-09|access-date=2010-05-26}} {{Webarchive|url=https://web.archive.org/web/20110809064625/http://www.oci.uzh.ch/efiles/OCVII/ja00315a037.pdf |date=2011-08-09 }}</ref> D. Bottger nyobaan nyieun adamantan maké éster Meerwein salaku prékursor. Hasilna, trisiklo-[3.3.1.1<sup>3,7</sup>], lain adamantan, tapi turunanana.<ref>S. Coffey, S. Rodd (ed.) Chemistry of Carbon Compounds. Vol 2. Part C. Elsevier Publishing Co.: New York. 1969</ref>

Kungsi ogé aya nu nyoba nyintésis adamantan maké floroglusinol sarta turunan [[siklohéksanon]], tapi sarua gagal.<ref name="cr64">{{Cite journal|last=Fort, Raymond C. Jr.|last2=Schleyers, Paul Von R.|year=1964|title=Adamantane: Consequences of Diamondoid Structure|journal=Chem. Rev.|volume=64|issue=3|pages=277–300|doi=10.1021/cr60229a004}}</ref> 
[[Gambar:Meerweins_Ether.png|kiri|jmpl| Éster Meerwein]]
Adamantan munggaran disintésis ku Vladimir Prelog taun [[1941]] ti éster Meerwein.<ref>{{Cite journal|year=1941|title=Über die Synthese des Adamantans|journal=Berichte|volume=74|issue=10|pages=1644–1648|doi=10.1002/cber.19410741004}}</ref><ref>{{Cite journal|year=1941|title=Über eine neue, ergiebigere Darstellung des Adamantans|journal=Berichte|volume=74|issue=11|pages=1769–1772|doi=10.1002/cber.19410741109}}</ref> Lian ti hasilna anu ukur saeutik 0,16%, carana ogé henteu praktis. Métode ieu dipaké pikeun nyintésis sababaraha turunan adamantan.<ref name="cr64"/> 
[[Gambar:Adamantane_synthesis_by_Prelog.png|pus|600x600px]]
Métode Prelog diropéa taun [[1956]]. Hasil dekarboksilasi ngalobaan ku ditambahan jalur Heinsdecker (11%) jeung réaksi Hoffman (24%) nepi ka hasilna jadi 6.5%.<ref>Stetter, H., Bander, O., and Neumann, W., Ber., 89, 1922 (1956).</ref><ref>{{Cite journal|last=McKervey|first=M|year=1980|title=Synthetic approaches to large diamondoid hydrocarbons|journal=Tetrahedron|volume=36|issue=8|pages=971–992|doi=10.1016/0040-4020(80)80050-0}}</ref> 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.<ref>{{Cite journal|last=Schleyer, P. von R.|year=1957|title=A Simple Preparation of Adamantane|journal=J. Am. Chem. Soc.|volume=79|issue=12|pages=3292–3292|doi=10.1021/ja01569a086}}</ref><ref>{{OrgSynth|author=Schleyer, P. von R.|author2=Donaldson, M. M.|author3=Nicholas, R. D.|author4=Cupas, C.|title=Adamantane|collvol=5|collvolpages=16|year=1973|prep=cv5p0016}}</ref> Sintésis adamantan ngaronjat jadi 60%<ref name="app">{{Cite book|url=https://books.google.com/books?id=0-FtXsmeX8oC&pg=PA50|pages=48–55|last=Mansoori, G. Ali|title=Molecular building blocks for nanotechnology: from diamondoids to nanoscale materials and applications|publisher=Springer|year=2007|isbn=0-387-39937-2}}</ref> jeung 98% maké katalis ultrasora jeung [https://books.google.com/books?id=SRzrCAAAQBAJ&pg=PA90&lpg=PA90&dq=high+yield+adamantane+synthesis&source=bl&ots=zyQmvWNBcr&sig=ffr4kix0Mv0Ia7OmTZDWCLDjmDs&hl=fi&sa=X&ved=0ahUKEwjq-5zQ-NTMAhURb5oKHVVGB1MQ6AEIKDAB#v=onepage&q=high%20yield%20adamantane%20synthesis&f=false katalis ultrasora jeung asam super].
[[Gambar:Adamantane_synthesis.png|pus|600x600px]]

== Kelimpahan alam ==
Saméméh disintésis, adamantan diisolasi tina minyak bumi ku kimiawan Céko: S. Landa, V. Machacek jeung M. Mzourek taun [[1932]].<ref name="landa">{{Cite journal|last=Landa, S.|last2=Machácek, V.|year=1933|title=Sur l'adamantane, nouvel hydrocarbure extrait de naphte.|url=http://cccc.uochb.cas.cz/5/0/0001/|journal=Collect. Czech. Chem. Commun.|volume=5|pages=1–5|doi=10.1135/cccc19330001}}</ref><ref>{{Citation|last=Landa, S.|title=Title unknown|url=https://books.google.com/books?id=Jh8hAQAAMAAJ|year=1933|ref=CITEREFLandaABC1933|last2=Machacek, V.|last3=Mzourek, M.|last4=Landa, M.|journal=Chim Ind. Spec. Publ. Vol. 506 (Abstracts of the 12th Conference of Industrial Chemistry, Prague, Sept. 1932); Chem. Abstr. 1933. Vol. 27. P. 5949.}}</ref> 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.<ref name="msu_pr">{{Cite web|url=http://www.chem.msu.su/rus/teaching/oil/spezprakt-adam.html|title=Synthesis of adamantane|language=Russian|accessdate=2009-12-11}} Special practical problem for the students of IV year. Department of Petroleum Chemistry and Organic Catalysis [[Moscow State University|MSU]].</ref><ref name="bagriy_2">{{Cite book|last=Bagriy EI|chapter=Methods for hydrocarbon adamantane series|title=Adamantane: Synthesis, properties, application|url=https://books.google.com/books?id=8RA2AAAAIAAJ&dq=isbn=502001382X|location=Moscow|publisher=Nauka|year=1989|pages=58–123|isbn=5-02-001382-X}}</ref>

== Pasipatan pisik ==
Adamantan murni tanwarna, kristalin padet nu bauna kawas kamper. Henteu leyur dina cai, tapi leyur dina [[pelarut organik]] nonpolar.<ref name="himicheskaya entsiklopediya">{{Cite web|url=http://www.chemport.ru/chemical_encyclopedia_article_18.html|title=Adamantane|website=Encyclopedia of Chemistry|language=Russian|accessdate=2009-12-11}}</ref> Salaku hidrokarbon, adamantan boga titik léé  anu kaasup luhur (270&nbsp;°C), bandingkeun jeung séjén hidrokarbon anu beurat molekulna sapantar: kampéna (45&nbsp;°C), limonéna (-74&nbsp;°C), osiména (50&nbsp;°C), terpinéna (60&nbsp;°C), twistana (164&nbsp;°C), atawa hidrokarbon liniér C<sub>10</sub>H<sub>22</sub> dékana (-28&nbsp;°C). Ahéngna, adamantan kalah nyublim lalaunan dina hawa kamar.<ref name="j1">{{Cite journal|last=Vijayakumar, V.|displayauthors=etal|year=2001|title=Pressure induced phase transitions and equation of state of adamantane|journal=J. Phys.: Condens. Matter|volume=13|issue=9|pages=1961–1972|bibcode=2001JPCM...13.1961V|doi=10.1088/0953-8984/13/9/318}}</ref> Adamantan bisa disuling maké saab cai.<ref name="bagriy_2"/>

=== Wangun ===
[[Gambar:Adamantane_molecular_parameters.png|ka|jmpl]]
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-[[hidrogén]]<nowiki/>na 1,112 Å.<ref name="bagriy_1"/>

== Tata ngaran ==
Dumasar kana aturan tata ngaran sistimatis, adamantan disebut trisiklo[3.3.1.1<sup>3,7</sup>]dékana. Sanajan kitu, IUPAC ngajak maké ngaran "adamantana".<ref name="iupac2013"/> 
[[Gambar:Adamantane_numbering.svg|kiri|100x100px]]

== Analog adamantan ==
Loba molekul niron wangun kandang kawas adamantan, kayaning fosfor trioksida P<sub>4</sub>O<sub>6,</sub> arsétrioksida aaAsO<sub>6</sub> fosfor pentoxikse a <sub>4</sub>O<sub>1</sub> = (PO) <sub>4</sub>O<sub>6</sub> fosfor pentasulfide a <sub>4</sub>S<sub>1</sub> = (PS)<sub>4</sub>S<sub>6</sub> sarta héksamétilénatétramina C<sub>6</sub>N<sub>4</sub>H<sub>12</sub> = N<sub>4</sub>(CH<sub>2)</sub><sub>6.</sub><ref>{{Cite journal|last=Vitall, J. J.|year=1996|title=The Chemistry of Inorganic and Organometallic Compounds with Adamantane-Like Structures|journal=[[Polyhedron (journal)|Polyhedron]]|volume=15|issue=10|pages=1585–1642|doi=10.1016/0277-5387(95)00340-1}}</ref> 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]].<ref>{{Cite journal|last=Fischer, Jelena|last2=Baumgartner, Judith|last3=Marschner, Christoph|year=2005|title=Synthesis and Structure of Sila-Adamantane|journal=[[Science (journal)|Science]]|volume=310|issue=5749|pages=825|doi=10.1126/science.1118981|pmid=16272116}}</ref> <gallery class="center">
Gambar: Adamantane acsv.svg|<nowiki> </nowiki>Adamantana 
Gambar: Hexamine.svg|<nowiki> </nowiki>[[Héksamétiléntétramina]] 
Gambar: Phosphorus-pentoxide-2D-dimensions.svg|<nowiki> </nowiki>[[Fosfor péntoksida]] 
Gambar: Phosphorus-pentasulfide-2D-dimensions.png|<nowiki> </nowiki>[[Fosfor péntasulfida]] 
Gambar: Tetramethylenedisulfotetramine.png|<nowiki> </nowiki>[[Tétramétiléndisulfotétramina]] 
Gambar: Tetrodotoxin.svg|<nowiki> </nowiki>[[Tétrodotoksin]] 
Gambar: Arsenicin A.png|<nowiki> </nowiki>[[Arsénisin A]] 
</gallery>

== Rujukan ==
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