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In organic chemistry, planar, three-connected carbon centers that are trigonal planar are often described as having sp 2 hybridization. [2] [3] Nitrogen inversion is the distortion of pyramidal amines through a transition state that is trigonal planar. Pyramidalization is a distortion of this molecular shape towards a tetrahedral molecular ...
In chemistry, orbital hybridisation (or hybridization) is the concept of mixing atomic orbitals to form new hybrid orbitals (with different energies, shapes, etc., than the component atomic orbitals) suitable for the pairing of electrons to form chemical bonds in valence bond theory.
In traditional hybridisation theory, the hybrid orbitals are all equivalent. [12] [27] Namely the atomic s and p orbital(s) are combined to give four sp i 3 = 1 ⁄ √ 4 (s + √ 3 p i) orbitals, three sp i 2 = 1 ⁄ √ 3 (s + √ 2 p i) orbitals, or two sp i = 1 ⁄ √ 2 (s + p i) orbitals. These combinations are chosen to satisfy two ...
They have central angles from 104° to 109.5°, where the latter is consistent with a simplistic theory which predicts the tetrahedral symmetry of four sp 3 hybridised orbitals. The most common actual angles are 105°, 107°, and 109°: they vary because of the different properties of the peripheral atoms (X).
Planarity results from the sp 2-hybridization of the mutually double-bonded carbon and the nitrogen atoms. The C=N distance is 1.29–1.31 Å for nonconjugated imines and 1.35 Å for conjugated imines. By contrast, C−N distances in amines and nitriles are 1.47 and 1.16 Å respectively. [4]
Bredt's rule also applies to carbocations and, to a lesser degree, free radicals, because these intermediates also prefer a planar geometry with 120° angles and sp 2 hybridization. It generally does not apply to hypervalent heteroatoms, although they are commonly written with a formal double bond. [6]
With nitrogen, we see the two molecular orbitals mixing and the energy repulsion. This is the reasoning for the rearrangement from a more familiar diagram. The σ from the 2p is more non-bonding due to mixing, and same with the 2s σ. This also causes a large jump in energy in the 2p σ* orbital.
In chemical bonds, an orbital overlap is the concentration of orbitals on adjacent atoms in the same regions of space. Orbital overlap can lead to bond formation. Linus Pauling explained the importance of orbital overlap in the molecular bond angles observed through experimentation; it is the basis for orbital hybridization.