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Radicals decrease in stability as they are closer to the nucleus, because the electron affinity of the orbital increases. As a general rule, hybridizations minimizing s-character increase the stability of radicals, and decreases the bond dissociation energy (i.e. sp 3 hybridization is most stabilizing).
Radical elimination can be viewed as the reverse of radical addition. In radical elimination, an unstable radical compound breaks down into a spin-paired molecule and a new radical compound. Shown below is an example of a radical elimination reaction, where a benzoyloxy radical breaks down into a phenyl radical and a carbon dioxide molecule. [7]
The ethoxy and cyano groups are able to delocalize the radical ion in the transition state, thus stabilizing the radical center. The rate enhancement is due to the captodative effect. When R = H, the reaction has the largest energy of activation because the radical center is not stabilized by the captodative effect.
Hyperconjugation can be used to rationalize a variety of chemical phenomena, including the anomeric effect, the gauche effect, the rotational barrier of ethane, the beta-silicon effect, the vibrational frequency of exocyclic carbonyl groups, and the relative stability of substituted carbocations and substituted carbon centred radicals, and the thermodynamic Zaitsev's rule for alkene stability.
The radical cyclization step usually involves the attack of a radical on a multiple bond. After this step occurs, the resulting cyclized radicals are quenched through the action of a radical scavenger, a fragmentation process, or an electron-transfer reaction. Five- and six-membered rings are the most common products; formation of smaller and ...
Phenyl groups (like all aromatic compounds) have enhanced stability in comparison to equivalent bonding in aliphatic (non-aromatic) groups. This increased stability is due to the unique properties of aromatic molecular orbitals. [2] The bond lengths between carbon atoms in a phenyl group are approximately 1.4 Å. [6]
Benzyl group and derivatives: Benzyl group, benzyl radical, benzyl amine, benzyl bromide, benzyl chloroformate, and benzyl methyl ether. R = heteroatom, alkyl, aryl, allyl etc. or other substituents. In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH 2 −C 6 H 5.
Carbon (6 C) has 14 known isotopes, from 8 C to 20 C as well as 22 C, of which 12 C and 13 C are stable. The longest-lived radioisotope is 14 C, with a half-life of 5.70(3) × 10 3 years. This is also the only carbon radioisotope found in nature, as trace quantities are formed cosmogenically by the reaction 14 N + n → 14 C + 1 H. The most ...