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The Collaborative International Dictionary

Substituent \Sub*stit"u*ent\, n. [L. substituens, p. pr. See Substitute.] (Chem.) Any atom, group, or radical substituted for another, or entering a molecule in place of some other part which is removed.


n. 1 (context chemistry English) any atom, group, or radical substituted for another, or entering a molecule in place of some other part which is removed 2 (context grammar English) pro-form


In organic chemistry and biochemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon, becoming a moiety of the resultant new molecule. The terms substituent, side chain, group, branch, or pendant group are used almost interchangeably to describe branches from a parent structure, though certain distinctions are made in the context of polymer chemistry. In polymers, side chains extend from a backbone structure. In proteins, side chains are attached to the alpha carbon atoms of the amino acid backbone.

The suffix yl is used when naming organic compounds that contain a single bond replacing one hydrogen; -ylidene and -ylidyne are used with double bonds and triple bonds, respectively. In addition, when naming hydrocarbons that contain a substituent, positional numbers are used to indicate which carbon atom the substituent attaches to when such information is needed to distinguish between isomers. The polar effect exerted by a substituent is a combination of the inductive effect and the mesomeric effect. Additional steric effects result from the volume occupied by a substituent.

The phrases most-substituted and least-substituted are frequently used to describe molecules and predict their products. In this terminology, methane is used as a reference of comparison. Using methane as a reference, for each hydrogen atom that is replaced or "substituted" by something else, the molecule can be said to be more highly substituted. For example:

  • Markovnikov's rule predicts that the hydrogen adds to the carbon of the alkene functional group that has the greater number of hydrogen atoms (fewer alkyl substituents).
  • Zaitsev's rule predicts that the major reaction product is the alkene with the more highly substituted (more stable) double bond.