Editing Pyrene (section)

{{short description|Chemical compound}}
{{other uses}}
{{chembox
| Watchedfields  = changed
| verifiedrevid  = 464376838
| Name           = Pyrene
| ImageFile      = Pyrene.svg
| ImageSize      = 190px
| ImageAlt       = Structural formula of pyrene
| ImageFile1     = Pyrene molecule from xtal ball.png
| ImageSize1     = 200px
| ImageAlt1      = Ball-and-stick model of the pyrene molecule
| ImageFile2 = Pyrene crystal 1.jpg
| PIN            = Pyrene<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=206 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| OtherNames     = Benzo[''def'']phenanthrene
| Section1       = {{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 39106
| SMILES = c1cc2cccc3c2c4c1cccc4cc3
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 29153
| PubChem = 31423
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14335
| InChI = 1/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H
| InChIKey = BBEAQIROQSPTKN-UHFFFAOYAB
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 279564
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BBEAQIROQSPTKN-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 129-00-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9E0T7WFW93
| RTECS = UR2450000
| Beilstein = 1307225
| Gmelin = 84203
  }}
| Section2       = {{Chembox Properties
| C=16 | H=10
| Appearance = colorless solid
(yellow impurities are often found at trace levels in many samples).
| Density = 1.271 g/cm<sup>3</sup><ref name=crc>Haynes, p. 3.472</ref>
| Solubility =  0.049 mg/L (0 °C)<br>0.139 mg/L (25 °C)<br>2.31 mg/L (75 °C)<ref>Haynes, p. 5.162</ref>
| MeltingPtC = 150.62
| MeltingPt_ref = <ref name=crc/>
| BoilingPtC = 394
| BoilingPt_ref = <ref name=crc/>
| MagSus = −147·10<sup>−6</sup> cm<sup>3</sup>/mol<ref>Haynes, p. 3.579</ref>
| LogP = 5.08<ref>Haynes, p. 5.176</ref>
| BandGap = 2.02 eV<ref>Haynes, p. 12.96</ref>
  }}
| Section3       = {{Chembox Structure
| Structure_ref=<ref>{{cite journal|doi=10.1107/S0365110X65001494 |title=The crystal and molecular structure of pyrene |date=1965 |last1=Camerman |first1=A. |last2=Trotter |first2=J. |journal=Acta Crystallographica |volume=18 |issue=4 |pages=636–643 |doi-access=free }}</ref>
| CrystalStruct = [[Monoclinic]]
| SpaceGroup = P2<sub>1</sub>/a
| PointGroup = 
| LattConst_a = 13.64 Å
| LattConst_b = 9.25 Å
| LattConst_c = 8.47 Å
| LattConst_alpha = 
| LattConst_beta = 100.28
| LattConst_gamma = 
| LattConst_ref =
| LattConst_Comment = 
| UnitCellVolume = 
| UnitCellFormulas = 4
  }}
| Section4       = {{Chembox Thermochemistry
| Thermochemistry_ref=<ref>Haynes, pp. 5.34, 6.161</ref>
| HeatCapacity = 229.7 J/(K·mol)
| Entropy = 224.9&nbsp;J·mol<sup>−1</sup>·K<sup>−1</sup>
| DeltaHf = 125.5&nbsp;kJ·mol<sup>−1</sup>
| DeltaHfus =  17.36&nbsp;kJ·mol<sup>−1</sup>
}}
| Section7       = {{Chembox Hazards
| ExternalSDS =
| MainHazards = irritant
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{HPhrases|H315 |H319 |H335 |H410 }}
| PPhrases = {{PPhrases|P261, |P264, |P271, |P273, |P280, |P302+P352, |P304+P340, |P305+P351+P338, |P312, |P321, |P332+P313, |P337+P313, |P362, |P391, |P403+P233, |P405|P501}}
| GHS_ref  =<ref>GHS: [https://pubchem.ncbi.nlm.nih.gov/compound/31423 PubChem]</ref>
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| FlashPt = non-flammable
  }}
| Section8       = {{Chembox Related
| OtherFunction_label = PAHs
| OtherFunction = [[benzopyrene]]
  }}
}}

'''Pyrene''' is a [[polycyclic aromatic hydrocarbon]] (PAH) consisting of four fused [[benzene]] rings, resulting in a flat [[Aromaticity|aromatic]] system.  The chemical formula is {{chem2|C16H10}}.  This yellow-green solid is the smallest peri-fused PAH (one where the rings are fused through more than one face).  Pyrene forms during [[Combustion#Incomplete|incomplete combustion]] of organic compounds.<ref>{{cite journal |doi=10.1021/cr100428a|title=Pyrene-Based Materials for Organic Electronics|year=2011|last1=Figueira-Duarte|first1=Teresa M.|last2=Müllen|first2=Klaus|journal=Chemical Reviews|volume=111|issue=11|pages=7260–7314|pmid=21740071}}</ref>