Short-lived molecule formed as a step of a chemical reaction
Not to be confused with Reaction intermediate.
In chemistry, a reactive intermediate or an intermediate is a short-lived, high-energy, highly reactive molecule. When generated in a chemical reaction, it will quickly convert into a more stable molecule. Only in exceptional cases can these compounds be isolated and stored, e.g. low temperatures, matrix isolation. When their existence is indicated, reactive intermediates can help explain how a chemical reaction takes place.[1][2][3][4]
Most chemical reactions take more than one elementary step to complete, and a reactive intermediate is a high-energy, hence unstable, product that exists only in one of the intermediate steps. The series of steps together make a reaction mechanism. A reactive intermediate differs from a reactant or product or a simple reaction intermediate only in that it cannot usually be isolated but is sometimes observable only through fast spectroscopic methods. It is stable in the sense that an elementary reaction forms the reactive intermediate and the elementary reaction in the next step is needed to destroy it.
When a reactive intermediate is not observable, its existence must be inferred through experimentation. This usually involves changing reaction conditions such as temperature or concentration and applying the techniques of chemical kinetics, chemical thermodynamics, or spectroscopy. Reactive intermediates based on carbon are radicals, carbenes, carbocations, carbanions, arynes, and carbynes.
^Carey, Francis A.; Sundberg, Richard J.; (1984). Advanced Organic Chemistry Part A Structure and Mechanisms (2nd ed.). New York N.Y.: Plenum Press. ISBN 0-306-41198-9.
^March Jerry; (1992). Advanced Organic Chemistry reactions, mechanisms and structure (4th ed.). New York: John Wiley & Sons ISBN 0-471-60180-2
^Gilchrist, T. L. (1966). Carbenes nitrenes and arynes. Springer US. ISBN 9780306500268.
^Moss, Robert A.; Platz, Matthew S.; Jones, Jr., Maitland (2004). Reactive intermediate chemistry. Hoboken, N.J.: Wiley-Interscience. ISBN 9780471721499.
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