Trigonal carbons

The carbonyl group is planar, with the sp2 carbon trigonal planar. The C=0 bond is polarized, with C partially positive and O partially negative. Many carbonyl reactions are initiated by nucleophilic addition to the partially positive carbon and completed by addition of a proton to the oxygen. 

The question of two rings going-on one is also seminal to the study of homoaromaticity. For n odd, the set of [(CH) CH2] ions demonstrate a delicate balance between mono and bicyclic structures (see Ref 133 and numerous references cited therein to both the experimental and theoretical literature). In the case of n = 3, one can imagine a planar cyclobutenyl cation (63) and a markedly non-planar, highly puckered bicyclobutyl cation (64). Both calculational theory on the parent and experiment on derivatives show the latter geometry to be preferred. However, as in the case of the other purported bicyclobutane derivatives characterized by the 2,4-carbons trigonally coordinated that were discussed earlier in this section, formal theory shows there is no 1,3-bond. The ion is not homoaromatic and there is no cyclopropane ring. In the case of n = 5,... 

Consider the electronic configuration of the cyclopentadienyl anion (Fig. 10.5). Each carbon, trigonally hybridized, is held by a a bond to two other carbons... 

As in the case of NH4 the charge is distributed over the whole ion. By considering each multiple bond to behave spatially as a single bond we are again able to use Table 2.8 to correctly deduce that the carbonate ion has a trigonal planar symmetry. Structures for other covalently-bonded ions can readily be deduced. 

In ethene the situation is rather different here, each carbon atom has one 2s and two 2p orbitals hybridised to form three sp single-pear orbitals which are trigonal planar (shown shaded in each half of Figure 2. JO). The remaining 2p orbital is not hybridised,... 

The element before carbon in Period 2, boron, has one electron less than carbon, and forms many covalent compounds of type BX3 where X is a monovalent atom or group. In these, the boron uses three sp hybrid orbitals to form three trigonal planar bonds, like carbon in ethene, but the unhybridised 2p orbital is vacant, i.e. it contains no electrons. In the nitrogen atom (one more electron than carbon) one orbital must contain two electrons—the lone pair hence sp hybridisation will give four tetrahedral orbitals, one containing this lone pair. Oxygen similarly hybridised will have two orbitals occupied by lone pairs, and fluorine, three. Hence the hydrides of the elements from carbon to fluorine have the structures... 

Carbon symmetry -letraheJnil isp ) C -C bond length 15.4 nm. trigonal planar sp ) C C bond length 14.2 nm interplanar distance 3J.5 nm... 

The carbon atoms of the double bond have a trigonal planar configuration and free rotation about the C—C bond is prevented by the n bond. The inability to rotate means that geometrical isomers can be produced, with substituents a and b, thus ... 

To ensure that the arrangement of four atoms in a trigonal planar environment (e.g., a sp -hybridized carbon atom) remains essentially planar, a quadratic term like V(0) = (fe/2) is used to achieve the desired geometry. By calculating the angle 9 between a bond from the central atom and the plane defined by the central... 

Formaldehyde (H2CO) H C=0 H Carbon has two bonded pairs + one double bond which is counted as one bonded pair Trigonal planar Trigonal planar ... 

Multiple bonds are treated as a single unit m the VSEPR model Formaldehyde is a trigonal planar molecule m which the electrons of the double bond and those of the two single bonds are maximally separated A linear arrangement of atoms m carbon diox ide allows the electrons m one double bond to be as far away as possible from the elec Irons m the other double bond... 

The geometry at carbon changes from tetrahedral trigonal planar linear... 

The chemistry of propylene is characterized both by the double bond and by the aHyUc hydrogen atoms. Propylene is the smallest stable unsaturated hydrocarbon molecule that exhibits low order symmetry, ie, only reflection along the main plane. This loss of symmetry, which implies the possibiUty of different types of chemical reactions, is also responsible for the existence of the propylene dipole moment of 0.35 D. Carbon atoms 1 and 2 have trigonal planar geometry identical to that of ethylene. Generally, these carbons are not free to rotate, because of the double bond. Carbon atom 3 is tetrahedral, like methane, and is free to rotate. The hydrogen atoms attached to this carbon are aUyflc. 

This comparison is further demonstrated by observing that the chemistry of both trigonal boron and carbonyl carbon are strongly influenced by the ready acceptance of attacking nucleophiles. 

Complex carbides are very numerous. Many newer compounds of this class have been discovered and their stmctures elucidated (20). The octahedron M C is typical where the metals arrange around a central carbon atom. The octahedra may be coimected via corners, edges, or faces. Trigonal prismatic polyhedra also occur. Defining T as transition metal and M as metal or main group nonmetal, the complex carbides can be classified as (/)... 

The C NMR spectrum of the metabolite shows 16 signals instead of 8 as expected from the elemental composition determined by high-resolution mass spectrometry. Moreover, aromaticity of the 2,6-xylenol is obviously lost after metabolism because two ketonic carbonyl carbon atoms (5c = 203.1 and 214.4) and four instead of twelve carbon signals are observed in the shift range of trigonal carbon nuclei (5c = 133.1, 135.4, 135.6 and 139.4) in the C NMR spectra. To conclude, metabolism involves oxidation of the benzenoid ring. 

Fumaric acid is converted to L-malic acid by hydration in the presence of the enzyme fumamse. From the structure of the substrate and the configuration of the product, it is apparent that the hydroxyl group has been added to the si fiice of one of the carbon atoms of the double bond. Each of the trigonal carbon atoms of an alkene has its fiice specified separately. The molecule of fumaric acid shown below is viewed fixjm the re-re fiice. 

Similarly, the two faces at a trigonal earbon in a molecule containing a stereogenic center are diastereotopie. Both ehiral and achiral reactants can distinguish between these diastereotopie faces. Many examples of diastereotopie transformations of sueh eompounds are known. One of the cases that has been examined elosely is addition reactions at a trigonal center adjacent to an asymmetric carbon. Particular attention has been given to the case of nucleophilie addition to carbonyl groups. 

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