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16-September-2008 16:15:15 - Adamantane Adamantane Adamantane Adamantane Adamantane IUPAC name Adamantane1 Other names Tricyclo3.3.1.13,7decane Identifiers CAS number 281-23-2 SMILES C1C2CC3CC1CCC2C3 Properties Molecular formula C10H16 Molar mass 136.23 g/mol Appearance White to off-white powder Density 1.07 g/cm³ 20 °C, solid Melting point 270 °C 543 K Solubility in water Poorly soluble Solubility in other solvents Soluble in hydrocarbons Structure Crystal structure face-centred cubic Dipole moment 0 D Hazards Main hazards Flammable S-phrases 24/25/28/37/45 Related compounds Related compounds: Memantine Rimantadine Amantadine Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Adamantane tricyclo3.3.1.13,7decane is a colourless, crystalline compound with a camphor-like odour.23 With a formula C10H16, it is a cycloalkane and also the simplest diamondoid. Adamantane was discovered in petroleum in 1933.4 Its name derived from the Greek adamantinos relating to steel or diamond, due to its diamond-like structure.5 Adamantane is the most stable isomer of C10H16. Contents 1 Synthesis 2 Uses 3 Adamantane derivatives 4 Adamantane analogues 5 References Synthesis Adamantane was first synthesised by Prelog in 1941.67 A more convenient method was found by Schleyer in 1957, from dicyclopentadiene by hydrogenation followed by acid-catalysed skeletal rearrangement.89 Uses Adamantane itself enjoys few applications since it is merely an unfunctionalised hydrocarbon. It is used in some dry etching masks.10 It is also used in some polymer formulations. In solid-state NMR spectroscopy, adamantane is a common standard for chemical shift referencing.11 In dye lasers, adamantane may be used to extend the life of the gain medium; it cannot be photoionised under atmosphere because its absorption bands lie in the vacuum-ultraviolet region of the spectrum. Photoionization energies have been determined recently for adamantane as well as for several bigger diamondoids.12 Adamantane derivatives Adamantane derivatives are useful in medicine, e.g. amantadine, memantine and rimantadine. Condensed adamantanes or diamondoids have been isolated from petroleum fractions, where they occur in small amounts. These species are of interest as molecular approximations of the cubic diamond framework, terminated with C-H bonds. 1,3-Dehydroadamantane is a member of the propellane family. Due to its stability, specific steric properties and conformational rigidity, the 1-adamantyl group is a bulky substituent in organic and organometallic chemistry. Some of the first persistent carbenes featured adamantyl substituents. Adamantane analogues Many molecules adopt cage structures with adamantanoid structures. Particularly useful compounds with this motif include P4O6, As4O6, P4O10 = PO4O6, P4S10 = PS4S6, and N4CH26.13 References ^ According to page 41 of a 2004 IUPAC guide, adamantane is the preferred IUPAC name. ^ SID 152429 -- PubChem Substance Summary. Retrieved on 14 October, 2005. ^ ADAMANTANETRICYCLO3.3.1.1DECANE. Retrieved on 14 October, 2005. ^ Landa, S.; Machácek, V. 1933. . Collection Czech. Chem. Commun. 5: 1. ^ Alexander Senning. Elsevier's Dictionary of Chemoetymology. Elsevier, 2006. ISBN 0444522395. ^ Prelog, V., Seiwerth,R. 1941. Über die Synthese des Adamantans. Berichte 74: 1644-1648. doi:10.1002/cber.19410741004. ^ Prelog, V., Seiwerth,R. 1941. Über eine neue, ergiebigere Darstellung des Adamantans. Berichte 74: 1769-1772. doi:10.1002/cber.19410741109. ^ Schleyer, P. von R. 1957. A Simple Preparation of Adamantane. J. Am. Chem. Soc. 79: 3292-3292. doi:10.1021/ja01569a086. ^ Schleyer, P. von R.; Donaldson, M. M.; Nicholas, R. D.; Cupas, C. Adamantane, Organic Syntheses, Coll. Vol. 5, p.16 1973; Vol. 42, p.8 1962. ^ ^ WATANABE, KEIJI; et al. 2001. RESIST COMPOSITION AND PATTERN FORMING PROCESS. United States Patent Application 20010006752. Bandwidth Market, Ltd. Retrieved on 14 October, 2005. ^ Corey R. Morcombe and Kurt W. Zilm 2003. Chemical Shift referencing in MAS solid state NMR. J. Magn. Reson. 162: 479-486. doi:10.1016/S1090-78070300082-X. ^ K. Lenzke, L. Landt, M. Hoener et al. 2007. Experimental determination of the ionization potentials of the first five members of the nanodiamond series. J. Chem. Phys. 127: 084320. doi:10.1063/1.2773725. ^ Vitall, J. J., The Chemistry of Inorganic and Organometallic Compounds with Adamantane-Like Structures, Polyhedron, 1996, 15, 1585-1642 Retrieved from http://en..org/wiki/Adamantane Categories: Cycloalkanes Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Italiano Nederlands Polski SlovenÄ?ina Suomi 䏿–‡ This page was last modified on 4 July 2008, at 12:38
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