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Annulene
Annulenes are monocyclic hydrocarbons that contain the maximum number of non-cumulated or conjugated double bonds (' mancude'). They have the general formula C''n''H''n'' (when ''n'' is an even number) or C''n''H''n''+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''nnulene' for the mancude hydrocarbon with ''n'' carbon atoms 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 nnulene and benzene is nnulene (and occasionally referred to as just 'annulene'). The discovery that 8nnulene 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 annul ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Annulenes
Annulenes are cyclic compound, monocyclic hydrocarbons that contain the maximum number of non-cumulated or conjugated double bonds ('wikt:mancude, mancude'). They have the general formula C''n''H''n'' (when ''n'' is an even number) or C''n''H''n''+1 (when ''n'' is an odd number). The IUPAC nomenclature, 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 atoms 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 [8]annulene and benzene is [6]annulene (and occasionally referred to as just 'annulene'). The discovery that [18]annulene possesses a number of key properties associated with other aromatic molecules was an important development in the understanding ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclodocosahendecaene
Annulenes are monocyclic hydrocarbons that contain the maximum number of non-cumulated or conjugated double bonds (' mancude'). They have the general formula C''n''H''n'' (when ''n'' is an even number) or C''n''H''n''+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''nnulene' for the mancude hydrocarbon with ''n'' carbon atoms 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 nnulene and benzene is nnulene (and occasionally referred to as just 'annulene'). The discovery that 8nnulene 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 annul ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclodecapentaene
Cyclodecapentaene or 0nnulene is an annulene with molecular formula C10H10. This organic compound is a conjugated 10 pi electron cyclic system and according to Huckel's rule it should display aromaticity. It is not aromatic, however, because various types of ring strain destabilize an all-planar geometry. Conformation, strain, and non-aromaticity Although not aromatic itself, 0nnulene can transition between different conformational isomers through aromatic or quasiaromatic excited states, such that its conformational isomerism is fixed only at extreme cryogenic temperatures. Understanding the composition and reactivity of these mixtures computationally has proven difficult, because a large number of conformations all minimize the energy locally. The all- ''cis'' isomer ( 1), a fully convex decagon, would have bond angles of 144°, which creates large amounts of angle strain relative t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclooctadecanonaene
Cyclooctadecanonaene or 8nnulene is an organic compound with chemical formula . It belongs to the class of highly conjugated compounds known as annulenes and is aromatic. The usual isomer that 8nnulene refers to is the most stable one, containing six interior hydrogens and twelve exterior ones, with the nine formal double bonds in the ''cis'',''trans'',''trans'',''cis'',''trans'',''trans'',''cis'',''trans'',''trans'' configuration. It is reported to be a red-brown crystalline solid. Aromaticity Notably, 8nnulene is the first annulene after benzene ( nnulene) to be fully aromatic: its π-system contains 4''n'' + 2 electrons (''n'' = 4), and it is large enough to comfortably accommodate six hydrogen atoms in its interior, allowing it to adopt a planar shape, thus satisfying Hückel's rule. The discovery of aromatic stabilization for 8nnulene is historically significant for confirming earlier theoretical predictions based on molecular orbital theory, since simple versions of vale ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Annulyne
In organic chemistry, annulynes or dehydroannulenes are conjugated monocyclic hydrocarbons with alternating single and double bonds in addition to at least one triple bond. They are related to annulenes, which only have alternating single and double bonds. The smallest member of this class is nnulyne but is never observed because the molecule carries too much angle strain. The next member is nnulyne or benzyne which is a reactive intermediate well known in organic chemistry. nnulyne is known to exist but quickly dimerizes or trimerizes; the compound has been trapped as its radical anion and observed by EPR spectroscopy. 0nnulyne, like nnulyne, only exists in theory. 2nnulyne has been observed in 2005 by Stevenson et al. in solution by NMR spectroscopy at room temperature. Reaction of 1,5-hexadiyne and potassium tert-butoxide was reported to yield two isomers 5,9-di-''trans''- 2annulyne and 3,11-di-''trans''- 2nnulyne in a 1:1 ratio. The proposed reaction sequence in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Antiaromaticity
Antiaromaticity is a chemical property of a cyclic molecule with a pi electron, π electron system that has higher energy, i.e., it is less stable due to the presence of 4n delocalised (π or lone pair) electrons in it, as opposed to aromaticity. Unlike aromatic compounds, which follow Hückel's rule ([4''n''+2] π electrons) and are highly stable, antiaromatic compounds are highly unstable and highly reactive. To avoid the instability of antiaromaticity, molecules may change shape, becoming non-planar and therefore breaking some of the π interactions. In contrast to the Aromatic ring current, diamagnetic ring current present in aromatic compounds, antiaromatic compounds have a paramagnetic ring current, which can be #Antiaromaticity in NMR Spectra, observed by NMR spectroscopy. Examples of antiaromatic compounds are pentalene (A), biphenylene (B), cyclopentadienyl cation (C). The prototypical example of antiaromaticity, cyclobutadiene, is the subject of debate, with some scienti ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclododecahexaene
Cyclododecahexaene or [12]annulene () is a member of the series of annulenes with some interest in organic chemistry with regard to the study of aromaticity. Cyclododecahexaene is non-aromatic due to the lack of planarity of the structure. On the other hand the dianion with 14 electrons is a Hückel's rule, aromatic by Hückel's rules and more stable. According to in silico experiments the tri-trans isomer is expected to be the most stable, followed by the 1,7-ditrans and the all cis-isomers (+1 kcal/mol) and by the 1,5-ditrans isomer (+5 kcal/mol). The first [12]annulene with sym-tri-trans configuration was synthesized in 1970 from a tricyclic precursor by photolysis at low temperatures. On heating the compound rearranges to a bicyclic [6.4.0] isomer. Organic reduction, Reducing the compound at low temperatures allowed analysis of the dianion by proton NMR with the inner protons resonating at −4.5 ppm relative to TMS, evidence of an aromatic diamagnetic ring current ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Circulene
A circulene is a macrocyclic arene in which a central polygon is surrounded and fused by benzenoids. Nomenclature within this class of molecules is based on the number of benzene rings surrounding the core, which is equivalent to the size of the central polygon. Examples which have been synthesized include irculene ( corannulene), irculene ( coronene), irculene, and 2irculene ( kekulene) These compounds belong to a larger class of geodesic polyarenes. Whereas irculene is bowl-shaped and irculene is planar, irculene has a unique saddle-shaped structure (compare to cones and partial cones in calixarenes). The helicenes are a conceptually related class of structures in which the array of benzene rings form an open helix rather than a closed ring. Quadrannulene ( irculene) The simple irculene compound itself has not been synthesized, but a derivative, tetrabenzo irculene, also called quadrannulene, has. irculenes The isolation of the irculene derivative 2,5,6,9,10,13, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclotetradecaheptaene
Cyclotetradecaheptaene, often referred to as 4nnulene, is a hydrocarbon with molecular formula C14H14, which played an important role in the development of criteria (Hückel's rule) for aromaticity, a stabilizing property of central importance in physical organic chemistry Physical organic chemistry, a term coined by Louis Hammett in 1940, refers to a discipline of organic chemistry that focuses on the relationship between chemical structures and chemical reaction, reactivity, in particular, applying experimental to .... It forms dark-red needle-like crystals. Structure and aromaticity Although the conjugated ring of 4 nnulene 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. There is evidence that it has two isomeric forms of comparable stability (''trans'', ''cis'', ' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclooctatetraene
1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as nnulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of its stoichiometric relationship to benzene, COT has been the subject of much research and some controversy. Unlike benzene, C6H6, cyclooctatetraene, C8H8, is not aromatic, although its dianion, ( cyclooctatetraenide), is. Its reactivity is characteristic of an ordinary polyene, i.e. it undergoes addition reactions. Benzene, by contrast, characteristically undergoes substitution reactions, not additions. History 1,3,5,7-Cyclooctatetraene was initially synthesized by Richard Willstätter in Munich in 1905 using pseudopelletierine as the starting material and the Hofmann elimination as the key transformation: : Willstätter noted that the compound did not exhibit the expected aromaticity. Between 1939 and 1943, chemists throughout ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triple Bond
A triple bond in chemistry is a chemical bond between two atoms involving six Electron pair bond, bonding electrons instead of the usual two in a covalent bond, covalent single bond. Triple bonds are stronger than the equivalent covalent bond, single bonds or double bond, double bonds, with a bond order of three. The most common triple bond is in a nitrogen N2 molecule; the second most common is that between two carbon atoms, which can be found in alkynes. Other functional groups containing a triple bond are cyanides and isocyanides. Some diatomic molecules, such as diphosphorus and carbon monoxide, are also triple bonded. In skeletal formula, skeletal formulae the triple bond is drawn as three parallel lines (≡) between the two connected atoms. Bonding Triple bonding can be explained in terms of orbital hybridization. In the case of acetylene, each carbon atom has two sp orbital, sp-orbitals and two p-orbitals. The two sp-orbitals are linear, with 180° bond angles, and occupy ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
