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According to the sigma bond rule, the number of sigma bonds in a molecule is equivalent to the number of atoms plus the number of rings minus one. N σ = N atoms + N rings − 1. This rule is a special-case application of the Euler characteristic of the graph which represents the molecule. A molecule with no rings can be represented as a tree ...
A simple ring contains the same number of sigma bonds as atoms, and a polycyclic ring system contains more sigma bonds than atoms. A molecule containing one or more rings is called a cyclic compound, and a molecule containing two or more rings (either in the same or different ring systems) is termed a polycyclic compound.
One electron forms a sigma bond with the hydrogen atom, and one is used in covalently bonding to each of the two neighboring carbons. This leaves six electrons, shared equally around the ring in delocalized pi molecular orbitals the size of the ring itself. [5] This represents the equivalent nature of the six carbon-carbon bonds all of bond order 1
In organic chemistry, neighbouring group participation (NGP, also known as anchimeric assistance) has been defined by the International Union of Pure and Applied Chemistry (IUPAC) as the interaction of a reaction centre with a lone pair of electrons in an atom or the electrons present in a sigma or pi bond contained within the parent molecule but not conjugated with the reaction centre.
The reaction center can be a p-or sp n-orbital (Woodward-Hoffmann symbol ω), a conjugated system (π) or even a sigma bond (σ). The relationship is antarafacial when opposite faces of the π system or isolated orbital are involved in the process (think anti). For a σ bond, it corresponds to involvement of one "interior" lobe and one ...
Bond length: Hyperconjugation is suggested as a key factor in shortening of sigma bonds (σ bonds). For example, the single C–C bonds in 1,3-butadiene and propyne are approximately 1.46 Å in length, much less than the value of around 1.54 Å found in saturated hydrocarbons. For butadiene, this can be explained as normal conjugation of the ...
The σ-π model differentiates bonds and lone pairs of σ symmetry from those of π symmetry, while the equivalent-orbital model hybridizes them. The σ-π treatment takes into account molecular symmetry and is better suited to interpretation of aromatic molecules ( Hückel's rule ), although computational calculations of certain molecules tend ...
In molecules which have resonance or nonclassical bonding, bond order may not be an integer.In benzene, the delocalized molecular orbitals contain 6 pi electrons over six carbons, essentially yielding half a pi bond together with the sigma bond for each pair of carbon atoms, giving a calculated bond order of 1.5 (one and a half bond).