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2005•Journal of Physical Organic ChemistryRequires access

Relation between resonance energy and substituent resonance effect in P‐phenols

Tadeusz M. Krygowski, Beata T. Stępień, Michał K. Cyrański, Krzysztof Ejsmont

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Abstract

Abstract Molecular geometries of phenol and its 17 p‐substituted derivatives were optimized at the B3LYP/6–311 + G** level of theory. Three homodesmotic and three isodesmotic reaction schemes were used to estimate aromatic stabilization energies (ASE) and the substituent effect stabilization energy (SESE). Other descriptors of π‐electron delocalization (HOMA and NICS, NICS(1) and NICS(1)zz) were also estimated. The SESE and ASE values correlated well with one another as well as with substituent constants. Much worse correlations with substituent constants were found for other aromaticity indices. The NICS(1)zz values are the most negative for unsubstituted phenol, indicating its highest aromaticity; that was not the case for NICS(1) and NICS. Copyright © 2005 John Wiley & Sons, Ltd.

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Abstract Molecular geometries of phenol and its 17 p‐substituted derivatives were optimized at the B3LYP/6–311 + G** level of theory. Three homodesmotic and three isodesmotic reaction schemes were used to estimate aromatic stabilization energies (ASE) and the substituent effect stabilization energy (SESE). Other descriptors of π‐electron delocalization (HOMA and NICS, NICS(1) and NICS(1)zz) were also estimated. The SESE and ASE values correlated well with one another as well as with substituent constants. Much worse correlations with substituent constants were found for other aromaticity indices. The NICS(1)zz values are the most negative for unsubstituted phenol, indicating its highest aromaticity; that was not the case for NICS(1) and NICS. Copyright © 2005 John Wiley & Sons, Ltd.

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Available abstract

Abstract Molecular geometries of phenol and its 17 p‐substituted derivatives were optimized at the B3LYP/6–311 + G** level of theory. Three homodesmotic and three isodesmotic reaction schemes were used to estimate aromatic stabilization energies (ASE) and the substituent effect stabilization energy (SESE). Other descriptors of π‐electron delocalization (HOMA and NICS, NICS(1) and NICS(1)zz) were also estimated. The SESE and ASE values correlated well with one another as well as with substituent constants. Much worse correlations with substituent constants were found for other aromaticity indices. The NICS(1)zz values are the most negative for unsubstituted phenol, indicating its highest aromaticity; that was not the case for NICS(1) and NICS. Copyright © 2005 John Wiley & Sons, Ltd.

Key concepts: Substituent, Chemistry, Aromaticity, Delocalized electron, Phenol, Resonance (particle physics), Electron delocalization, Computational chemistry

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