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cross-conjugation

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.
Source:
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1101
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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.C01404.
Original PDF version: http://www.iupac.org/goldbook/C01404.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 The PDF version is out of date and is provided for reference purposes only.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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