| Revision as of 00:32, 28 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|← Previous edit |
Latest revision as of 01:09, 27 October 2024 edit undoSashimiteishoku (talk | contribs)6 editsmNo edit summary |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 404019796 |
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| verifiedrevid = 447061584 |
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| ImageFile = Phenyl oxalate ester.png |
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| ImageFile = Diphenyl oxalate.svg |
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| ImageSize = 220 |
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| ImageSize = 200 |
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| ImageName = Skeletal formula |
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| ImageAlt = Skeletal formula of diphenyl oxalate |
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| ImageFile1 = Diphenyl-oxalate-3D-balls.png |
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| ImageFile1 = Diphenyl oxalate 3D ball.png |
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| ImageSize1 = 220 |
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| ImageSize1 = 220 |
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| ImageName1 = Ball-and-stick model |
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| ImageAlt1 = Ball-and-stick model of the diphenyl oxalate molecule |
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| IUPACName = diphenyl oxalate |
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| PIN = Diphenyl oxalate |
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| OtherNames = diphenylethandioate, oxalic acid diphenyl ester, cyalume, DPO |
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| OtherNames = diphenylethandioate, oxalic acid diphenyl ester, cyalume, DPO |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 3155-16-6 |
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| PubChem = 18475 |
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| CASNo = 3155-16-6 |
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| SMILES = O=C(Oc1ccccc1)C(=O)Oc2ccccc2 |
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| PubChem = 18475 |
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| SMILES = O=C(Oc1ccccc1)C(=O)Oc2ccccc2 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 17449 |
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| InChI = 1/C14H10O4/c15-13(17-11-7-3-1-4-8-11)14(16)18-12-9-5-2-6-10-12/h1-10H |
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| InChIKey = ULOZDEVJRTYKFE-UHFFFAOYAB |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C14H10O4/c15-13(17-11-7-3-1-4-8-11)14(16)18-12-9-5-2-6-10-12/h1-10H |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ULOZDEVJRTYKFE-UHFFFAOYSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>14</sub>H<sub>10</sub>O<sub>4</sub> |
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| Formula = C<sub>14</sub>H<sub>10</sub>O<sub>4</sub> |
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| MolarMass = 242.227 g/mol |
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| MolarMass = 242.227 g/mol |
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| Appearance = solid |
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| Appearance = solid |
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| Density = |
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| Density = |
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| MeltingPtC = 136 |
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| MeltingPtC = 136 |
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| BoilingPt = |
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| BoilingPt = |
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| Solubility = |
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| Solubility = |
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}} |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| MainHazards = |
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| Autoignition = |
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| FlashPt = |
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| AutoignitionPt = |
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|Section4={{Chembox Thermochemistry |
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| DeltaGf = |
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| DeltaHc = |
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| DeltaHf = 129·0 ± 0·8<ref>{{cite journal|last1=Carson|first1=A. S.|last2=Fine|first2=D. H.|last3=Gray|first3=P.|last4=Laye|first4=P. G.|title=Standard enthalpies of formation of diphenyl oxalate and benzoic anhydride and some related bond dissociation energies|journal=Journal of the Chemical Society B: Physical Organic|date=1971|pages=1611|doi=10.1039/J29710001611}}</ref> |
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| Entropy = |
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| HeatCapacity = |
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}} |
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| Section9 = {{Chembox Related |
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| OtherAnions = |
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| OtherCations = |
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| OtherFunction = |
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| OtherCompounds = ] |
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'''Diphenyl oxalate''' (trademark name '''Cyalume''') is a solid ] whose ] products are responsible for the ] in a ]. It can be synthesized by fully esterifying ] with ]. The reaction with ] that diphenyl oxalate undergoes to produce a photon of ] is shown below: |
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'''Diphenyl oxalate''' (trademark name '''Cyalume''') is a solid whose ] products are responsible for the ] in a ]. This chemical is the double ] of ] with ]. Upon reaction with ], ] is formed, along with release of the two phenols.<ref>{{cite journal|last1=Orosz|first1=György|title=The role of diaryl oxalates in peroxioxalate chemiluminescence|journal=Tetrahedron|date=January 1989|volume=45|issue=11|pages=3493–3506|doi=10.1016/S0040-4020(01)81028-0}}</ref> The dioxetanedione then reacts with a ] molecule, decomposing to form ] and leaving the dye in an ]. As the dye relaxes back to its unexcited state, it releases a ] of visible light. |
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The reaction rate is pH dependent, and slightly alkaline conditions achieved by adding a weak base, e.g., ], will produce brighter light. |
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The reaction rate is pH dependent, and slightly ] conditions, achieved by adding a weak base, such as ], give a faster reaction and therefore produce brighter light. |
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The ] ester of ] is a solid and thus easier to handle. Furthermore, since trichlorophenolate is the better leaving group, the reaction will proceed faster, again producing brighter light, as compared to the phenol ester. |
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The ] is a solid and thus easier to handle.{{clarify|reason=the diphenyl itself is also a solid|date=February 2019}} Furthermore, since trichlorophenolate is the better leaving group, the reaction will proceed faster, again producing brighter light, as compared to the phenol ester. |
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The following colors can be produced by using different dyes: |
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The following colors can be produced by using different dyes: |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist}} |
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