Diamond Essay Example For Students

Diamond Essay The unique nature of diamond is heavily dependent upon its composition, crystalstructure, and mechanical, thermal, and electromagnetic properties.1 Of thosedependencies, composition exacts the most influence over the characteristics. Crystal structure is the repeating pattern of diamonds composition, and eachof the properties are the result of molecular interaction which is determined bycomposition. Therefore, composition is paramount in the determination of thequalities of diamond. Before its discovery, adamantane was known as decaterpene,the name applied by Decker to his tricyclic hydrocarbon. Decker believed thathis decaterpene was similar in structure as the diamond lattice. Decaterpene, asin diamond, was proposed by Decker to be highly structured and strain free.2Decker proposed decaterpene in 1924, but that was all it was until 1933 when thestructure was proven to exist. Isolated in the petroleum of Hodinin,Czechoslovakia by Landa and Machachaeck, decaterpene became incarnate.3 However,the fact that they found the structure Decker predicted did not mean that hisnomenclature would be used to identify the compound. That honor was bestowedupon its discoverers Landa and Machcahcaeck who used the Greek translati on ofdiamond, adamantane, to identify the compound.2 Crude petroleum is separatedinto its component compounds by fractional distillation. The procedure involvesa sample of the petroleum to be heated until the sample is vaporized leavingbehind any solid impurities. The resulting steam enters a fractionaldistillation column in which a temperature gradient had been instilled. Thetemperature of the column decreases as the steam rises through the column. Theidea is that, as the temperature of the column decreases, the vapor temperaturewill decrease. When the boiling point of a compound is passed, the compound willcondense on the sides of the column and be collected in the fraction well atthat point. Thus the mixture is separated into fractions of compounds withsimilar boiling points in a mixture.4 Adamantanes high boiling point causedit to be one of the initial compounds to condense with the kerosene fraction inthe 190o C cut.5 The only problem with the fractional distillation method ist hat adamantane cannot be extracted in large quantities because it exists inonly a small quantity in petrol. The presence of adamantane was found to be only0.0004% of the composition of petroleum by the fractional distillation method.2Adamantane is not alone in the petroleum distillate in which it is present. We will write a custom essay on Diamond specifically for you for only $16.38 $13.9/page Order now Alkylated adamantane derivatives also show up in adamantane containingdistillate. (II, III, IV) The output of adamantane is capable of being increasedif the thiourea adduct method is employed on the petroleum. Landa and Hale wereable to isolate complexes of adamantane from crude petroleum that had bonded tothiourea.5 Now that the natural product has been discovered, the next logicalstep would be to formulate the natural process in which the compound was made. As of 1964, the natural method that creates the adamantane compound had not beenfound. The natural process that was attempted was to bombard adamantane-freepetroleum with catalysts in an attempt to initiate the formation of adamantane. The resulting mixture was fractioned and analyzed to see if any extra adamantanewas created. In most cases, the catalyst failed to produce any adamantane. However, many of the catalysts produced derivatives that had the ring structurebut with extra components attached.5 The only catalyst shown to make asignificant amount was AlCl3, but not enough was created for the catalyst to beconsidered for mass production of adamantane. Catalysts that failed were:oil-bearing stone from Hodin with and without HF, aluminum silicate, aluminumoxide, concentrated sulfuric acid, zinc chloride, iron(III) chloride, tin(IV)chloride, antimony(V) chloride.5 It is believed that the reason many of thecatalysts did not work, even though they are present in natural petroleum, isthat the conditions that they were subjected to were experimental in nature. Thecreation of adamantane is thought to be a biogenesis of petroleum under a set ofconditions that is not able to be recreated in the lab.2 With the naturalmechanism a mystery, a synthetic method to create the compound was sought afterto allow the study of adamantane to proceed. After all, with Landa in completec ontrol of the slim supply of adamantane, the cost of adamantane skyrocketed.6Two methods were investigated to be able to create the natural adamantanestructure: ring closure and isomerization. Before adamantane was known to theworld, the starting material commonly used to synthesize adamantane and itsderivatives through ring closure was being developed. In 1922, Meerwein wasinvestigating a way to remove the bridgehead carboxymethoxy group of ringcompounds, and reseal the ring structure with diiodomethane(V) and sodium. Hisexperiments failed because the malonic ester(VI) which he created forced thereactant groups too far apart for the recycling to occur.3,4 Despite hisfailures, Meerwein was able to inspire other advancements of his researchthrough the malonic ester which came to bear his name as Meerweins ester.7This became the common starting point for the search for the path to cyclicadamantane. Bottger was the first to make great strides in the adamantanesynthesis research followi ng Meerweins lead. Starting with Meerweins esterBottger was able to bring the ring together to create a cyclic product.6 Theproduct was of the tricyclo- decane ring system of which adamantaneis a constituent, but Bottgers product still had external functional groupsaround the ring instead of the only hydrogen around adamantane.5 As a result,what Bottger had synthesized was not adamantane, but a derivative of it. Thefirst synthesis of true adamantane did not occur until 1937 when Prelog andSeiworth were able to advance the work of Bottger, and decarboxylize the ringstructure leaving behind only the basic ring.6 Adamantane was their finalproduct, but that product still was not produced in large quantities. The systemused by Prelog and Seiworth yielded an output of adamantane at 0.16% of thematerials going into it.7 As often occurs in science, the advancements made byPrelog and Seiworth were furthered by the research of others. Landa reenteredthe adamantane research realm with Stetter. Together, they were able to improvethe efficiency of Prelog and Seiworths overall synthesis. Decarboxylationyield was increased by the addition of the Heinsdecker pathway (11%), and theHoffman reaction (24%). Even with the advancements, synthesis of adamantane byring closure was never able to yield an output over 6.5% of the reactants.5Nevertheless, the process developed by Bottger remained an efficient method forthe synthesis of derivatives. This left research of adamantane to be inferredthrough the experimentation of adamantanes derivatives since its synthesiswas not economical. This was true until 1957 when Paul von R. Schleyeraccidentally synthesized adamantane. Schleyer was working on the inversion ofreversible endo-exo isomerization of tetrahydrodicyclopentadiene.3 During hisexperimentation, he noticed that the reaction had a side product of a whitecrystalline compound. The compound was set aside and investigated later. Themysterious compound was found to have a melting point that matched theexperimental adamantane melting point. Other adamantane-like characteristicslater solidified his compound as a match. Schleyers discovery of anisomerization method of adamantane synthesis rocked the scientific community, asit provided a more efficient method for adamantane production. Schleyer was ableto increase the output of his adamantane synthesis to a 30% and 40% yield byexposing the tetrahydrodicyclopentadiene to an AlCl3-HCl mixture under 40 atms. .u7d3547518919bc98e8d7003b6a895739 , .u7d3547518919bc98e8d7003b6a895739 .postImageUrl , .u7d3547518919bc98e8d7003b6a895739 .centered-text-area { min-height: 80px; position: relative; } .u7d3547518919bc98e8d7003b6a895739 , .u7d3547518919bc98e8d7003b6a895739:hover , .u7d3547518919bc98e8d7003b6a895739:visited , .u7d3547518919bc98e8d7003b6a895739:active { border:0!important; } .u7d3547518919bc98e8d7003b6a895739 .clearfix:after { content: ""; display: table; clear: both; } .u7d3547518919bc98e8d7003b6a895739 { display: block; transition: background-color 250ms; webkit-transition: background-color 250ms; width: 100%; opacity: 1; transition: opacity 250ms; webkit-transition: opacity 250ms; background-color: #95A5A6; } .u7d3547518919bc98e8d7003b6a895739:active , .u7d3547518919bc98e8d7003b6a895739:hover { opacity: 1; transition: opacity 250ms; webkit-transition: opacity 250ms; background-color: #2C3E50; } .u7d3547518919bc98e8d7003b6a895739 .centered-text-area { width: 100%; position: relative ; } .u7d3547518919bc98e8d7003b6a895739 .ctaText { border-bottom: 0 solid #fff; color: #2980B9; font-size: 16px; font-weight: bold; margin: 0; padding: 0; text-decoration: underline; } .u7d3547518919bc98e8d7003b6a895739 .postTitle { color: #FFFFFF; font-size: 16px; font-weight: 600; margin: 0; padding: 0; width: 100%; } .u7d3547518919bc98e8d7003b6a895739 .ctaButton { background-color: #7F8C8D!important; color: #2980B9; border: none; border-radius: 3px; box-shadow: none; font-size: 14px; font-weight: bold; line-height: 26px; moz-border-radius: 3px; text-align: center; text-decoration: none; text-shadow: none; width: 80px; min-height: 80px; background: url(https://artscolumbia.org/wp-content/plugins/intelly-related-posts/assets/images/simple-arrow.png)no-repeat; position: absolute; right: 0; top: 0; } .u7d3547518919bc98e8d7003b6a895739:hover .ctaButton { background-color: #34495E!important; } .u7d3547518919bc98e8d7003b6a895739 .centered-text { display: table; height: 80px; padding-left : 18px; top: 0; } .u7d3547518919bc98e8d7003b6a895739 .u7d3547518919bc98e8d7003b6a895739-content { display: table-cell; margin: 0; padding: 0; padding-right: 108px; position: relative; vertical-align: middle; width: 100%; } .u7d3547518919bc98e8d7003b6a895739:after { content: ""; display: block; clear: both; } READ: Vegetarian Diet Essayof pressure of hydrogen and HF-BF3 catalyst respectively.7 When Schleyer focusedhis procedure on the retrieval of adamantane, he found that the synthesis wasbountiful with the starting reactant dicyclopentadiene which is a commoncompound.3 Research into the enigmatic compound could then proceeded full forcefrom this point on to examine the compound to its every minute detail. What theyfound confirmed their previous assertions that adamantane was unlike anycarbohydrate known to man. That carbohydrate was found to be a three fusedchairs of cyclohexane rings bound only to hydrogen atoms. The crystallizedstructure of adamantane was studied in depth by X-ra y diffraction. An X-raydiffraction pattern is created through the interaction of photons emitted froman excited metal atom with the crystal form of a compound. The photon eithermisses the crystal atoms or is deflected by the atom. Most photons miss theatoms, but those deflected do so in a regular pattern because of the repetitiousnature of crystals. That pattern may be recorded through the use of a strip ofphotographic film or a two-dimensional array detector to provide a hard copy ofthe deflection pattern.8 Thus the crystalline lattice type, distance betweenatoms, and number of atoms per unit cell may be found by analysis of thediffraction pattern. The crystal orientation is a face centered cubic latticethat was completely separate from all known carbohydrate crystal orientation.6Face centered cubic means that there are atoms centered at the faces of the cubeas well as at the corners. Adamantane was derived to have a tetragonal spacegroup with four molecules per unit cell, and the vector quantities a = 6.60A andc = 8.81A.7 The carbon bond lengths and angles were stereotypically sound asthey were measured to be 1.54 _ 0.01A and 109.5 _ 1.5o respectively.6 This datashowed proof that adamantane was a stable compound, but how stable they did notknow until the physical qualities were determined. The melting point wasdetermined by sealed tube, and was found to be 269oC which is the melting pointfor adamantane exposed to the atmosphere as well as the highest melting pointfor a carbohydrate.9 It is unusual for such an occurrence, but adamantane has noend to its surprises. The exact boiling point of adamantane is impossible to bedetermined for it is incapable of being reached except by mixture with othercarbohydrates at which time the boiling point is 190oC. It is this property thatallowed adamantane to be discovered by fractionalization.6 The enigmatic natureof adamantane is reinforced by the fact that it has such a high melting andboiling point, yet it remains true that adamantane will sublime at roomtemperature and atmospheric pressure. Now that adamantanes crysatllinestructure is known along with the physical properties, what remains is fortechnology to fill in the blanks as far as molecular interactions of thecompound. Adamantane was subjected to NMR and IR(Fig 1,2) Each test producedresults that were unique for any carbohydrate upon which the same conditionswere exerted.5 The most probable reason for such unique results is thesymmetrical nature of adamantane. In fact, adamantane has a symmetry number oftwelve which is unheard of in a carbohydrate. This means that throughout thestructure there exists a combination of planes and axes about which adamantaneis symmetrical or identical that totals twelve. Many compounds, organic andinorganic, are symmetrical in one or two dimensions, but few are symmetrical inthree dimensions as adamantane is. NMR uses the magnetic nature of atom nucleito its advantage. By surrounding a compound in a magnetic f ield, the nucleibecome vulnerable to excitation by radiation in the radiofrequency range. Theradiofrequency that the nuclei absorb is dependent upon the environment thenuclei are exposed to as far as the neighboring nuclei and those the nuclei arebonded to.10 In this case, a proton NMR showed adamantane as only a sharpdoublet with a spacing of 0.95 ppm.(Fig 1) The symmetry of adamantane isperfectly supported by these NMR results because only a doublet means that allof the protons are identical in nature. This shows that each proton in thestructure of adamantane is sharing each of the electrons equally creating astrong dependence of resonance by all protons.6 The singularity in the NMRresult becomes an important diagnostic tool for determination of the purity ofan adamantane perspective. Any substitution anywhere on the ring would unbalanceresonance of the compound that would be picked up by the NMR in the form ofanother series of peaks indicating an adamantane derivative as long as thedoublet remains present. IR results are much the same as those of NMR in thatadamantane itself gives a clear result while any impurity clouds those results. .u8d393e26765fa938ec02ddb82d8e06a1 , .u8d393e26765fa938ec02ddb82d8e06a1 .postImageUrl , .u8d393e26765fa938ec02ddb82d8e06a1 .centered-text-area { min-height: 80px; position: relative; } .u8d393e26765fa938ec02ddb82d8e06a1 , .u8d393e26765fa938ec02ddb82d8e06a1:hover , .u8d393e26765fa938ec02ddb82d8e06a1:visited , .u8d393e26765fa938ec02ddb82d8e06a1:active { border:0!important; } .u8d393e26765fa938ec02ddb82d8e06a1 .clearfix:after { content: ""; display: table; clear: both; } .u8d393e26765fa938ec02ddb82d8e06a1 { display: block; transition: background-color 250ms; webkit-transition: background-color 250ms; width: 100%; opacity: 1; transition: opacity 250ms; webkit-transition: opacity 250ms; background-color: #95A5A6; } .u8d393e26765fa938ec02ddb82d8e06a1:active , .u8d393e26765fa938ec02ddb82d8e06a1:hover { opacity: 1; transition: opacity 250ms; webkit-transition: opacity 250ms; background-color: #2C3E50; } .u8d393e26765fa938ec02ddb82d8e06a1 .centered-text-area { width: 100%; position: relative ; } .u8d393e26765fa938ec02ddb82d8e06a1 .ctaText { border-bottom: 0 solid #fff; color: #2980B9; font-size: 16px; font-weight: bold; margin: 0; padding: 0; text-decoration: underline; } .u8d393e26765fa938ec02ddb82d8e06a1 .postTitle { color: #FFFFFF; font-size: 16px; font-weight: 600; margin: 0; padding: 0; width: 100%; } .u8d393e26765fa938ec02ddb82d8e06a1 .ctaButton { background-color: #7F8C8D!important; color: #2980B9; border: none; border-radius: 3px; box-shadow: none; font-size: 14px; font-weight: bold; line-height: 26px; moz-border-radius: 3px; text-align: center; text-decoration: none; text-shadow: none; width: 80px; min-height: 80px; background: url(https://artscolumbia.org/wp-content/plugins/intelly-related-posts/assets/images/simple-arrow.png)no-repeat; position: absolute; right: 0; top: 0; } .u8d393e26765fa938ec02ddb82d8e06a1:hover .ctaButton { background-color: #34495E!important; } .u8d393e26765fa938ec02ddb82d8e06a1 .centered-text { display: table; height: 80px; padding-left : 18px; top: 0; } .u8d393e26765fa938ec02ddb82d8e06a1 .u8d393e26765fa938ec02ddb82d8e06a1-content { display: table-cell; margin: 0; padding: 0; padding-right: 108px; position: relative; vertical-align: middle; width: 100%; } .u8d393e26765fa938ec02ddb82d8e06a1:after { content: ""; display: block; clear: both; } READ: To Kill a Mockingbird: The Influences Parents have EssaySpecifically, adamantane gives a major doublet in the region of 2926 cm-1 with a0.8983 transmittance, and other peaks shown on Figure 2. This means that aroundthe adamantane compound exists methyl groups that are similar in nature andsurrounding environment. Consequently, all bonds absorb the same wavelengthsthat suggests identical motion of each of the bonds whether that be stretching,scissoring, or other. Any variance in a functional group would result in theabsorbance wavelength to change. Therefore, an increase in the number of peaksand a decrease in intensity of the existing peaks would occur because the changein bonding pattern would limit or expand the possible motions of the bonds. Eachbond-motion type absorbs a different wavelength in the IR, so any change in thetypes changes the absorbances. IR translates the amount transmitted perwavelength to an electrical signal that is interpreted through fourier transformto an IR spectrogram.10 Absorbance is the inverse of transmittance, so anychange in absorbance changes the transmittance and the ending spectrogramvalues. Since adamantane is so symmetrical and stable, it becomes the perfectbasis for many studies and research. In fact the universality of adamantane isso great that it is capable of being used for: structure reactivityrelationships, development of empirical force field methods, orientationdisorder probe model, and structure basis for drugs.5 The possibilities areendless for adamantane and its uses simply because of its simplicity in natureand structure allow for a structure that is one of the most unique and strong innature. Bibliography1. M. Shen, H.F. Schaeffer III, C. Liang, J. Lii, N.L. Allinger, and P.v.R. Schleyer. J. Am. Chem., 114, 497 (1992) 2. B. J. Mair, M. Shainenger, N.C. Krouskov, and F.D. Rossini, Anal. Chem., 31, 2082 (1959) 3. P. von RagueSchleyer, J. Am. Chem. Soc., 79, 3292 (1957) 4. R.M. Roberts, J.C. Gilbert, S.F. Martin. Experimental Organic Chemistry. Harcourt Brace College Publishers:Philadelphia, PA. 1994. 5. M. A. McKervey, Tetrahedron, 36, 971 (1980) 6. R. C. Fort, and P. von Rogue Schleyer, Chem. Rev., 64, 277 (1964) 7. S. Coffey, ed. Rodds Chemistry of Carbon Compounds. Vol 2. Part C. Elsevier Publishing Co.:New York. 1969. 8. D.A. McQuarrie, J.D. Simon. Phhysical Chemistry: A MolecularApproach. University Science Books: Sausalito, CA. 1997. 9. Adamantane.Dictionary of Organic Compounds. Vol 1. 5th ed., Buckingham, J. ed. Chapman andHall: New York. 1982. 10. Ege, Seyhan. Organic Chemistry: Structure andReactivity. 3rd ed. D.C. Heath and Co.: Lexington, MA. 1994.