The effect (on reaction rates,
ionization equilibria, etc.) attributed to a substituent due to overlap of its p- or
π-orbitals with the p- or
π-orbitals of the rest of the
molecular entity.
Delocalization is thereby introduced or extended, and electronic charge may flow to or from the substituent. The effect is symbolized by M. Strictly understood, the mesomeric effect operates in the ground
electronic state of the molecule. When the molecule undergoes electronic excitation or its energy is increased on the way to the
transition state of a
chemical reaction,
the mesomeric effect may be enhanced by the
electromeric effect, but this term is not much used, and the mesomeric and electromeric effects tend to be subsumed in the term
resonance effect of a
substituent.
Source:
PAC, 1994, 66, 1077
(Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994))
on page 1139
Cite as:
IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A.Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8.
doi:10.1351/goldbook.