ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Differential Effects of Nitrogen Substitution in 5- and 6-Membered Aromatic Motifs.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
7 citing papers in PubMed, 13 citations in OpenAlex.
- Biocompatible Chemistry: A Plug-and-Play Toolbox for Chemical Biology Research.Chembiochem : a European journal of chemical biology · 2025Review
- Combined Inductive and Dispersion Effects Enhance Bioorthogonal Reactivity of Tetrazines Toward Isonitriles.Angewandte Chemie (International ed. in English) · 2025Article
- Mutually Orthogonal Bioorthogonal Reactions: Selective Chemistries for Labeling Multiple Biomolecules Simultaneously.Topics in current chemistry (Cham) · 2024Review
- Orthogonal Inverse-Electron-Demand Cycloaddition Reactions Controlled by Frontier Molecular Orbital Interactions.Organic letters · 2023Article
- Spirocyclization enhances the Diels-Alder reactivities of geminally substituted cyclopentadienes and 4Journal of physical organic chemistry · 2023Article
- Enhancement of oil forensic methodology through the addition of polycyclic aromatic nitrogen heterocycle biomarkers for diagnostic ratios.Environmental monitoring and assessment · 2023Article
- Insights into the Factors Controlling the Origin of Activation Barriers in Group 13 Analogues of the Four-Membered N-Heterocyclic Carbenes.ACS omega · 2021Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The replacement of carbon with nitrogen can affect the aromaticity of organic rings. Nucleus-independent chemical shift (NICS) calculations at the center of the aromatic π-systems reveal that incorporating nitrogen into 5-membered heteroaromatic dienes has only a small influence on aromaticity. In contrast, each nitrogen incorporated into benzene results in a sequential and substantial loss of aromaticity. The contrasting effects of nitrogen substitution in 5-membered dienes and benzene are reflected in their Diels-Alder reactivities as dienes. 1,2-Diazine experiences a 10
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