Sp2 orbital

The O atom uses one of its sp or sp hybrids to form the CO a bond and antibond. When sp hybrids are used in conceptualizing the bonding, the other sp hybrid forms a lone pair orbital directed away from the CO bond axis one of the atomic p orbitals is involved in the CO n and 71 orbitals, while the other forms an in-plane non-bonding orbital. Alternatively, when sp hybrids are used, the two sp hybrids that do not interact with the C-atom sp2 orbital form the two non-bonding orbitals. Hence, the final picture of bonding, non-bonding, and antibonding orbitals does not depend on which hybrids one uses as intermediates. 

When we discussed sp3 hybrid orbitals in Section 1.6, we said that the four valence-shell atomic orbitals of carbon combine to form four equivalent sp3 hybrids. Imagine instead that the 2s orbital combines with only two of the three available 2p orbitals. Three sp2 hybrid orbitals result, and one 2p orbital remains unchanged- The three sp2 orbitals lie in a plane at angles of 120° to one another, with the remaining p orbital perpendicular to the sp2 plane, as shown in Figure 1.13. 

Figure 1.14 The structure of ethylene. Orbital overlap of two sp hybridized carbons forms a carbon-carbon double bond. One part of the double bond results from a (head-on) overlap of sp2 orbitals (green), and the other part results from (sideways) overlap of unhybridized p orbitals (red/blue). The ir bond has regions of electron density on either side of a line drawn between nuclei.

We saw in Chapter 1 that the carbon-carbon double bond can be described in two ways. In valence bond language (Section 1.8), the carbons are sp2-hybridized and have three equivalent hybrid orbitals that lie in a plane at angles of 120° to one another. The carbons form a cr bond by head-on overlap of sp2 orbitals and a tt bond by sideways overlap of unhybridized p orbitals oriented... 

What accounts for the stability of conjugated dienes According to valence bond theory (Sections 1.5 and 1.8), the stability is due to orbital hybridization. Typical C—C bonds like those in alkanes result from a overlap of 5p3 orbitals on both carbons. In a conjugated diene, however, the central C—C bond results from conjugated diene results in part from the greater amount of s character in the orbitals forming the C-C bond. 

Bonds formed by overlap Bond formed by overfap of sp3 orbitals of sp2 orbitals... 

Figure 15.8 Pyridine and pyrimidine are nitrogen-containing aromatic heterocycles with tt electron arrangements much like that of benzene. Both have a lone pair of electrons on nitrogen in an sp2 orbital in the plane of the ring.

Figure 16.19 An orbital picture and electrostatic potential map of benzyne. The benzyne carbons are sp2-hybridized, and the "third" bond results from weak overlap of two adjacent sp2 orbitals.

A nucleophilic addition reaction to an aldehyde or ketone. The nucleophile approaches the carbonyl group from an angle of approximately 75° to the plane of the sp2 orbitals, the carbonyl carbon rehybridizes from sp2 to sp3, and an alkoxide ion is formed. 

Purine has three basic, pyridine-like nitrogens with lone-pair electrons in sp2 orbitals in the plane of the ring. The remaining purine nitrogen is nonbasic and pyrrole-like, with its lone-pair electrons as part of the aromatic i- electron system. 

An oxygen atom can also form a double bond to carbon thus in propanone (acetone), Me2C=Q , the oxygen atom could use three sp2 hybrid orbitals one to form a a bond by overlap with an sp2 orbital of the carbon atom, and the other two to accommodate the two lone pairs of electrons. This leaves an unhybridised p orbital on both oxygen and carbon, and these can overlap with each other laterally (cf. C=C, p. 9) to form a n bond ... 

Both carbon atoms in ethene undergo sp2 hybridization. The C-H bonds involve overlap of sp1 carbon orbitals with Is orbitals of the H atoms. The carbon-carbon double bond involves the overlap of sp2 orbitals from each carbon to give the o bond and the side-on overlap of a p orbital from each carbon atom to give the n bond. 

Carbon atoms (1) and (4) use sp3 hybrid orbitals to form four sigma bonds, three by overlap with the hydrogen Is orbitals and one by overlap with an sp2 orbital from the central carbon (2). The two carbon atoms involved in the double bond undergo sp2 hybridization. They form C-H bonds by overlapping with Is orbitals of the H atoms. The C=C double bond is formed similarly to that described in (a). 

The sp2 orbitals are equivalent, coplanar and oriented at 120° to each other and form ct bonds by overlap with orbitals of neighbouring atoms, as in the molecule ethene, C2H4, Fig. 1, A2. The remaining p orbital on each C atom forms a n bond by overlap with the p orbital from the neighbouring C atom the bonds formed between two C atoms in this way are represented as Csp2=Csp2, or simply as C=C. 

Photolysis of vinyldiazomethane in an organic glass at 6 K leads to vinylcarbene in its triplet ground state,14,56,57 which — as is indicated by the ESR spectra — forms a pair of the s-cis and s-trans isomer. The delocalization of one unpaired electron in the rr-system is similar to that of the allyl radical, while the other unpaired electron is localized in a sp2-orbital at the carbenic C atom (see formula T-33 ).58... 

It is found experimentally that boron can form three covalent bonds. But as it has only one unpaired valence electron in the ground state, it appears only to be able to form one bond. To create three unpaired electrons, one electron in the 2s orbital is promoted to the 2py orbital. To form three identical bonds with the same energy, two p and one s orbitals mix to give three sp2 orbitals. These three identical and half filled sp2 orbitals enable boron to form three identical bonds. 

In the Walash model each carbon atom has an sp2 orbital which is directed towards the centre of the ring and a p orbital the lobes of which overlap with the p orbitals of the adjacent carbons. These p lobes can overlap with other p lobes in a conjugated n system. So the plane of the ring becomes parallel to the plane in which the rest of the n system lies. 

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