Aromaticity and Antiaromaticity in Five‐Membered C4H4X Ring Systems: “Classical” and “Magnetic” Concepts May Not Be “Orthogonal”

Paul von Ragué Schleyer; Haijun Jiao; Bernd Goldfuß; Peter K. Freeman

doi:10.1002/anie.199503371

Abstract

Energetic, geometric, and magnetic criteria yield quantitatively the same order of aromaticity (antiaromaticity) for the five-membered ring systems 1: the aromatic 6π electron systems are stabilized, their bond lengths are equalized, and the magnetic susceptibility exaltations are diamagnetic. In contrast, the antiaromatic 4π electron systems are destabilized, double bonds are localized, and susceptibility exaltations are paramagnetic.

Keywords

AntiaromaticityAromaticityDiamagnetismRing (chemistry)Magnetic susceptibilityChemistryParamagnetismYield (engineering)CrystallographyRing currentComputational chemistryMaterials scienceCondensed matter physicsPhysicsMoleculeMagnetic fieldOrganic chemistryQuantum mechanics

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Publication Info

Year: 1995
Type: article
Volume: 34
Issue: 3
Pages: 337-340
Citations: 542
Access: Closed

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APA Style

                            
                                
                                    Paul von Ragué Schleyer, 
                                
                                    Haijun Jiao, 
                                
                                    Bernd Goldfuß
                                
                                et al.
                            
                            (1995). 
                            Aromaticity and Antiaromaticity in Five‐Membered C<sub>4</sub>H<sub>4</sub>X Ring Systems: “Classical” and “Magnetic” Concepts May Not Be “Orthogonal”. 
                            Angewandte Chemie International Edition in English
                            , 34
                            (3)
                            , 337-340.
                            https://doi.org/10.1002/anie.199503371
                        

Identifiers

DOI: 10.1002/anie.199503371