Vicinal (chemistry) explained

In chemistry the descriptor vicinal (from Latin vicinus = neighbor), abbreviated vic, is a descriptor that identifies two functional groups as bonded to two adjacent carbon atoms (i.e., in a 1,2-relationship). It may arise from vicinal difunctionalization.

Relation of atoms in a molecule

For example, the molecule 2,3-dibromobutane carries two vicinal bromine atoms and 1,3-dibromobutane does not. Mostly, the use of the term vicinal is restricted to two identical functional groups.

Likewise in a gem-dibromide the prefix gem, an abbreviation of geminal, signals that both bromine atoms are bonded to the same atom (i.e., in a 1,1-relationship). For example, 1,1-dibromobutane is geminal. While comparatively less common, the term hominal has been suggested as a descriptor for groups in a 1,3-relationship.[1]

Like other descriptors, such as syn, anti, exo or endo, the description vicinal helps explain how different parts of a molecule are related to each other either structurally or spatially. The vicinal adjective is sometimes restricted to those molecules with two identical functional groups. The use of the term can also be extended to substituents on aromatic rings.

1H-NMR spectroscopy

\phi

is described by the Karplus relation.

Notes and References

  1. Book: Nickon, Alex. Organic Chemistry: The Name Game. Silversmith. Ernest F.. Pergamon Press. 1987. 0-08-034481-X. New York. registration.
  2. D. H. Williams, I. Fleming: Strukturaufklärung in der organischen Chemie; Eine Einführung in die spektroskopischen Methoden, 6. überarbeitete Auflage, Georg Thieme Verlag, Stuttgart 1991, S. 105.