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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 431384079 |
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| verifiedrevid = 443551114 |
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| Name = Cyclotetradecaheptaene |
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| Name = Cyclotetradecaheptaene |
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| ImageFile = (14)Annulene.svg |
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| ImageFileL1 = (14)Annulene.svg |
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| ImageSize = 150px |
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|ImageFileR1=(14)Annulene-3D-balls.png |
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| ImageName = annulene |
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| IUPACName = (1''E'',3''Z'',5''E'',7''Z'',9''E'',11''E'',13''Z'')-cyclotetradeca-1,3,5,7,9,11,13-heptaene |
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| IUPACName = (1''E'',3''Z'',5''E'',7''Z'',9''E'',11''E'',13''Z'')-cyclotetradeca-1,3,5,7,9,11,13-heptaene |
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| OtherNames = Annulene |
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| OtherNames = Annulene |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| PubChem = 11988275 |
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| PubChem = 11988275 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10160742 |
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| ChemSpiderID = 10160742 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 37523 |
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| ChEBI = 37523 |
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| SMILES = c1ccccccccccccc1 |
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| SMILES = C1C=CC=CC=CC=CC=CC=CC=1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=1S/C14H14/c1-2-4-6-8-10-12-14-13-11-9-7-5-3-1/h1-14H/b2-1-,3-1-,4-2+,5-3+,6-4+,7-5+,8-6-,9-7-,10-8+,11-9+,12-10+,13-11+,14-12-,14-13- |
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| StdInChI=1S/C14H14/c1-2-4-6-8-10-12-14-13-11-9-7-5-3-1/h1-14H/b2-1-,3-1-,4-2+,5-3+,6-4+,7-5+,8-6-,9-7-,10-8+,11-9+,12-10+,13-11+,14-12-,14-13- |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RYQWRHUSMUEYST-ILUIUFOYSA-N |
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| StdInChIKey = RYQWRHUSMUEYST-ILUIUFOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 2873-14-5 |
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| CASNo = 2873-14-5 |
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| RTECS = |
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| RTECS = |
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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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| C=14|H=14 |
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| C=14 | H=14 |
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| Appearance = |
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| Appearance = dark-red needle-like crytals |
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| Density = |
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| Density = |
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| Solubility = Insoluble |
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| Solubility = Insoluble |
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| SolubleOther = Soluble |
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| SolubleOther = Soluble |
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| Solvent = ] |
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| Solvent = ] |
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| MeltingPt = |
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| MeltingPt = |
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| BoilingPt = |
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| BoilingPt = |
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| pKa = |
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| pKa = |
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| pKb = |
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| pKb = |
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| Viscosity = |
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| Viscosity = |
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}} |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| Structure_ref = <ref name="cryst"/> |
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| MolShape = |
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| Coordination = |
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| MolShape = |
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| Coordination = |
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| CrystalStruct = |
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| CrystalStruct = monoclinic |
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| Dipole = |
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| Dipole = |
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| SpaceGroup = P2<sub>1</sub>/c, No. 14 |
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| LattConst_a = 8.640 Å |
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| LattConst_b = 4.376 Å |
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| LattConst_c = 14.997 Å |
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| LattConst_beta = 106 |
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| UnitCellFormulas = 2 molecules per cell |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = Flammable, reactive |
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| MainHazards = Flammable, reactive |
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| FlashPt = |
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| FlashPt = |
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| RPhrases = |
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| SPhrases = |
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}} |
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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherAnions = |
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| OtherAnions = |
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| OtherCations = |
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| OtherCations = |
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| OtherCpds = |
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| OtherCompounds = |
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}} |
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'''Cyclotetradecaheptaene''', often referred to as '''annulene''', is a ] with molecular formula C<sub>14</sub>H<sub>14</sub>, which played an important role in the development of criteria (]) for ], a stabilizing property of central importance in ]. It forms dark-red needle-like crystals.<ref name="cryst">{{cite journal|last=Chiang|first=Chian C.|last2=Paul|first2=Iain C.|title=Crystal and Molecular Structure of Annulene|journal=]|year=1972|volume=94|issue=13|pages=4741–4743|doi=10.1021/ja00768a058}}</ref> |
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'''Cyclotetradecaheptaene''' is an aromatic ] with molecular formula C<sub>14</sub>H<sub>14</sub>. It is somewhat unstable due to ]. |
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== Structure and aromaticity == |
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Although the conjugated ring of ] contains 4''n''+2 electrons, it only exhibits limited evidence for being aromatic. It does not fully conform to Hückel's rule because none of its ''cis''/''trans'' isomers can adopt a completely planar conformation due to crowding of the interior hydrogens.<ref>{{cite book | title = Aromatic Character and Aromaticity | page = 96 | author = G. M. Badger | publisher = Cambridge University Press}}</ref> There is evidence that it has two isomeric forms of comparable stability (''trans'', ''cis'', ''trans'', ''cis'', ''trans'', ''trans'', ''cis''- with four interior hydrogens (shown in the infobox) and ''trans'', ''cis'', ''trans'', ''cis'', ''trans'', ''cis'', ''cis-'' with three interior hydrogens) which rapidly interconvert at room temperature but can be observed at low temperature by NMR.<ref>{{Cite book|url=https://archive.org/details/mechanismtheoryi000321|title=Mechanism and theory in organic chemistry|last=H.|first=Lowry, Thomas|date=1987|publisher=Harper & Row|others=Richardson, Kathleen Schueller.|isbn=0060440848|edition=3rd|location=New York|oclc=14214254|url-access=registration}}</ref> Its <sup>1</sup>H NMR spectrum shows evidence of aromatic ring currents that result in an upfield shift for the interior hydrogens. In contrast, the corresponding -]] and annulenes, which are weakly ] or nonaromatic, have downfield shifted interior hydrogens. However, unlike the undoubtedly aromatic annulene]], annulene does not bear the hallmark aromatic property of chemical stability, and it quickly decomposes when exposed to light and air.<ref>{{cite journal | doi = 10.1021/ja01506a061| title = Unsaturated Macrocyclic Compounds. XV. Cyclotetradecaheptaene| journal = Journal of the American Chemical Society| volume = 82| issue = 21| pages = 5765–5766| year = 1960| last1 = Sondheimer| first1 = Franz| last2 = Gaoni| first2 = Yehiel}}</ref> |
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==References== |
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{{reflist}} |
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{{Annulenes}} |
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] |
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] |
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] |
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{{hydrocarbon-stub}} |