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{{DISPLAYTITLE:5-Dehydro-''m''-xylylene}} |
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{{DISPLAYTITLE:5-Dehydro-''m''-xylylene}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 366685457 |
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| verifiedrevid = 425003182 |
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| Name = 5-Dehydro-''m''-xylylene |
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| Name = 5-Dehydro-''m''-xylylene |
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| ImageFile = DMX_line.png |
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| ImageFile = DMX_line.png |
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| OtherNames = 5-dehydro-''m''-xylylene,<br />DMX |
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| OtherNames = 5-dehydro-''m''-xylylene,<br />DMX |
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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 = 681440-83-5 |
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| CASNo = 681440-83-5 |
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| SMILES = C(C1)=C-=C-C=1 |
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| StdInChI=1S/C8H7/c1-7-4-3-5-8(2)6-7/h4-6H,1-2H2 |
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| StdInChIKey=FISNMDKRRJMFAO-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>8</sub>H<sub>7 |
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| Formula = C<sub>8</sub>H<sub>7</sub> |
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| MolarMass = 103.14 g/mol |
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| MolarMass = 103.14 g/mol |
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'''5-Dehydro-''m''-xylylene''' (DMX) is an ] ] ] and the first known organic molecule to violate ].<ref>{{cite journal | author = L Slipchenko ''et al.'' | title = 5-Dehydro-1,3-quinodimethane: A Hydrocarbon with an Open-Shell Doublet Ground State | journal = Angewandte Chemie International Edition | year = 2004 | volume = 43 | pages = 742 | doi = 10.1002/anie.200352990 | pmid = 14755709 | issue = 6}}</ref> |
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'''5-Dehydro-''m''-xylylene''' (DMX) is an ] ] tri] and the first known organic molecule to violate ].<ref>{{cite journal | author = L Slipchenko | title = 5-Dehydro-1,3-quinodimethane: A Hydrocarbon with an Open-Shell Doublet Ground State | journal = Angewandte Chemie International Edition | year = 2004 | volume = 43 | pages = 742–5 | doi = 10.1002/anie.200352990 | pmid = 14755709 | issue = 6|display-authors=etal}}</ref> |
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Its electronic ground state is an "] doublet" rather than a quartet; that is, it contains three low-] coupled unpaired electrons in three singly occupied ]s. Because there are radical electrons in both spin states, this compound is said to exhibit ]. Though similar ground states are observed in molecules containing transition metal atoms, it is unprecedented in organic molecules. |
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Its electronic ] is an ] doublet rather than a quartet; that is, the unpaired electrons in the three singly occupied ]s form a low-] state in which one electron has its spin-state opposed to the other two. The net result is that there is only one unopposed spin. Hund's rule would predict that the ground state would have all three radical electrons with the same spin-state as each other (none opposed), for a greater total spin. As a result of having non-paired electrons in both spin states coupled together, this compound exhibits ]. Though similar ground states are observed in molecules containing transition metal atoms, it is unprecedented in organic molecules. |
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The 5-dehydro-''m''-xylylene anion (DMX<sup>-</sup>) has also been studied extensively. It has a triplet ground state consisting of a phenyl anion and a ''m''-xylylene ]. |
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The 5-dehydro-''m''-xylylene anion (DMX<sup>−</sup>) has also been studied extensively. It has a triplet ground state consisting of a phenyl anion and a ''m''-xylylene ]. |
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==References== |
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==References== |
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==External links== |
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==External links== |
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