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mesomeric effect

Also contains definition of: resonance effect

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
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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.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.M03844.
Original PDF version: http://www.iupac.org/goldbook/M03844.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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