Dissected Nucleus-Independent Chemical Shift Analysis of π-Aromaticity and Antiaromaticity

Paul von Ragué Schleyer; Mariappan Manoharan; Zhi-Xiang Wang; Boggavarapu Kiran; Haijun Jiao; Ralph Puchta; Nicolaas J R van Eikema Hommes

doi:10.1021/ol016217v

Dissected Nucleus-Independent Chemical Shift Analysis of π-Aromaticity and Antiaromaticity

Org Lett. 2001 Aug 9;3(16):2465-2468. doi: 10.1021/ol016217v.

Authors

Paul von Ragué Schleyer¹, Mariappan Manoharan¹, Zhi-Xiang Wang¹, Boggavarapu Kiran¹, Haijun Jiao¹, Ralph Puchta¹, Nicolaas J R van Eikema Hommes¹

Affiliation

¹ Department of Chemistry, Computational Chemistry Annex, University of Georgia, Athens, Georgia 30602, and Computational Chemistry Center and Institute of Organic Chemistry, University of Erlangen-Nuremberg, Henkestrasse 42, D-91054 Erlangen, Germany.

PMID: 29446959
DOI: 10.1021/ol016217v

Abstract

Analysis of the basic π-aromatic (benzene) and antiaromatic (cyclobutadiene) systems by dissected nucleus-independent chemical shifts (NICS) shows the contrasting diatropic and paratropic effects, but also reveals subtleties and unexpected details.