Substituent Effects on the Basicity of Patriscabrin A and Lettucenin A: Evolution Favors the Aromatic?

[Image: see text] Basicities for derivatives of patriscabrin A and lettucenin A were calculated with density functional theory. A significant correlation is observed between the basicity and Hammett σ parameters. Protonation increases the aromatic character of the cyclic moieties of each natural pro...

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Autores principales: Prasad, Supreeth, Tantillo, Dean J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8582057/
https://www.ncbi.nlm.nih.gov/pubmed/34778640
http://dx.doi.org/10.1021/acsomega.1c04051
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author Prasad, Supreeth
Tantillo, Dean J.
author_facet Prasad, Supreeth
Tantillo, Dean J.
author_sort Prasad, Supreeth
collection PubMed
description [Image: see text] Basicities for derivatives of patriscabrin A and lettucenin A were calculated with density functional theory. A significant correlation is observed between the basicity and Hammett σ parameters. Protonation increases the aromatic character of the cyclic moieties of each natural product. The naturally occurring structures are predicted to be the most aromatic.
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spelling pubmed-85820572021-11-12 Substituent Effects on the Basicity of Patriscabrin A and Lettucenin A: Evolution Favors the Aromatic? Prasad, Supreeth Tantillo, Dean J. ACS Omega [Image: see text] Basicities for derivatives of patriscabrin A and lettucenin A were calculated with density functional theory. A significant correlation is observed between the basicity and Hammett σ parameters. Protonation increases the aromatic character of the cyclic moieties of each natural product. The naturally occurring structures are predicted to be the most aromatic. American Chemical Society 2021-10-29 /pmc/articles/PMC8582057/ /pubmed/34778640 http://dx.doi.org/10.1021/acsomega.1c04051 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Prasad, Supreeth
Tantillo, Dean J.
Substituent Effects on the Basicity of Patriscabrin A and Lettucenin A: Evolution Favors the Aromatic?
title Substituent Effects on the Basicity of Patriscabrin A and Lettucenin A: Evolution Favors the Aromatic?
title_full Substituent Effects on the Basicity of Patriscabrin A and Lettucenin A: Evolution Favors the Aromatic?
title_fullStr Substituent Effects on the Basicity of Patriscabrin A and Lettucenin A: Evolution Favors the Aromatic?
title_full_unstemmed Substituent Effects on the Basicity of Patriscabrin A and Lettucenin A: Evolution Favors the Aromatic?
title_short Substituent Effects on the Basicity of Patriscabrin A and Lettucenin A: Evolution Favors the Aromatic?
title_sort substituent effects on the basicity of patriscabrin a and lettucenin a: evolution favors the aromatic?
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8582057/
https://www.ncbi.nlm.nih.gov/pubmed/34778640
http://dx.doi.org/10.1021/acsomega.1c04051
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