Term: cross-conjugation
https://doi.org/10.1351/goldbook.C01404

Definition:
In a system XC6H4GY this is conjugation involving the substituent X, the benzene ring and the side-chain connective-plus-reaction site GY, i.e. either X is a +R group and GY is a -R group, or X is a -R group and GY is a +R group. In Hammett correlations this situation can lead to the need to apply exalted substituent constants σ + or σ-, respectively, as in electrophilic or nucleophilic aromatic substitution, respectively. The term 'through resonance' is synonymous. Cross conjugation has also been used to describe the interactions occurring in 2-phenylallyl and similar systems.

Related Terms:
1) conjugation (http://doi.org/10.1351/goldbook.C01267).
2) resonance (http://doi.org/10.1351/goldbook.R05326).

Source: PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1101 (https://doi.org/10.1351/pac199466051077)

Citation: 'cross-conjugation' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. https://doi.org/10.1351/goldbook.C01404

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