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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.
An example of such a rearrangement is the shift of substituents on tropilidenes (1,3,5-cycloheptatrienes). When heated, the pi-system goes through an electrocyclic ring closing to form bicycle[4,1,0]heptadiene (norcaradiene). Thereafter follows a [1,5] alkyl shift and an electrocyclic ring opening. norcaradiene rearrangement
According to the frontier molecular orbital theory, the sigma bond in the ring will open in such a way that the resulting p-orbitals will have the same symmetry as the HOMO of the product. [4] For the 5,6-dimethylcyclohexa-1,3-diene, only a disrotatory mode would result in p-orbitals having the same symmetry as the HOMO of hexatriene.
An electrocyclic reaction is a pericyclic reaction involving the net loss of a pi bond and creation of a sigma bond with formation of a ring. This reaction proceeds through either a conrotatory or disrotatory mechanism. In the conrotatory ring opening of cyclobutene, there are two electrons moving suprafacially (on the pi bond) and two moving ...
In the halogenation of benzene, the sigma complex comprises the six carbon atoms of the benzene ring, each bonded to a hydrogen atom. An additional halogen atom is bonded to one of the carbon atoms, which is sp 3-hybridized, while the other carbons remain sp 2-hybridized.
For hydrocarbons, the DBE (or IHD) tells us the number of rings and/or extra bonds in a non-saturated structure, which equals the number of hydrogen pairs that are required to make the structure saturated, simply because joining two elements to form a ring or adding one extra bond (e.g., a single bond changed to a double bond) in a structure reduces the need for two H's.
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.