Product Code Database
Annulenes are cyclic compound that contain the maximum number of non-cumulated or conjugated double bonds ( ), and their derivatives. They have the general formula Cn Hn (when n is an even number) or Cn Hn +1 (when n is an odd number). The IUPAC accepts the use of 'annulene nomenclature' in naming carbocyclic ring systems with 7 or more carbon atoms, using the name 'n annulene' for the mancude hydrocarbon with n carbon in its ring, though in certain contexts (e.g., discussions of aromaticity for different ring sizes), smaller rings (n = 3 to 6) can also be informally referred to as annulenes. Using this form of nomenclature 1,3,5,7-cyclooctatetraene is 8annulene and benzene is 6annulene (and occasionally referred to as just 'annulene').Ege, S. (1994) Organic Chemistry:Structure and Reactivity 3rd ed. D.C. Heath and CompanyDublin City University Annulenes ''
The discovery that 18annulene possesses a number of key properties associated with other aromatic molecules was an important development in the understanding of aromaticity as a chemical concept.
In the related , one double bond is replaced by a triple bond.
| +Aromaticity of the even annulenes ! n !aromaticity | |
| 4 | antiaromatic |
| 6 | aromatic |
| 8 | nonaromatic |
| 10 | nonaromatic |
| 12 | weakly antiaromatic |
| 14 | weakly aromatic |
| 16 | nonaromatic |
| 18 | aromatic |
Annulenes may be aromatic (benzene, 6annulene and 18annulene), non-aromatic (8 and 10annulene), or Antiaromaticity (cyclobutadiene, 4annulene). Cyclobutadiene is the only annulene with considerable antiaromaticity, since planarity is unavoidable. With 8annulene, the molecule takes on a tub shape that allows it to avoid conjugation of double bonds. 10Annulene is of the wrong size to achieve a planar structure: in a planar conformation, ring strain due to either steric hindrance of internal hydrogens (when some double bonds are trans) or bond angle distortion (when the double bonds are all cis) is unavoidable. Thus, it does not exhibit appreciable aromaticity.
When the annulene is large enough, 18annulene for example, there is enough room internally to accommodate hydrogen atoms without significant distortion of bond angles. 18Annulene possesses several properties that qualify it as aromatic. However, none of the larger annulenes are as stable as benzene, as their reactivity more closely resembles a conjugated polyene than an aromatic hydrocarbon.
In general, charged annulene species of the form (; ; ) are aromatic, provided a planar conformation can be achieved. For instance, , , and are all known aromatic species.
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