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On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation

On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation
On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation
A mesoionic bicycle, easily synthesized from a proteinogenic amino acid, L-leucine, behaves as both thiazolium-olate and diazolium-olate dipoles, as unveiled by its dipolar cycloadditions. This chameleonic reactivity has been thoroughly interpreted by dissecting the mechanistic landscape aided by the distortion–interaction model.
1477-0520
4778-4783
García de la Concepción, Juan
d8ca3ced-6c21-4c16-82e8-9b50611f4dc1
Ávalos, Martín
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Cintas, Pedro
8b9e8dcb-111f-4baa-8736-502d4b75b563
Jimenez, Jose
5b1200a0-13b8-4831-8985-2a0e3049ac03
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
García de la Concepción, Juan
d8ca3ced-6c21-4c16-82e8-9b50611f4dc1
Ávalos, Martín
2d0b39c7-15a3-4f90-bdfb-8e4b6e69c64a
Cintas, Pedro
8b9e8dcb-111f-4baa-8736-502d4b75b563
Jimenez, Jose
5b1200a0-13b8-4831-8985-2a0e3049ac03
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161

García de la Concepción, Juan, Ávalos, Martín, Cintas, Pedro, Jimenez, Jose and Light, Mark (2018) On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation. Organic & Biomolecular Chemistry, 16, 4778-4783. (doi:10.1039/C8OB01195H).

Record type: Article

Abstract

A mesoionic bicycle, easily synthesized from a proteinogenic amino acid, L-leucine, behaves as both thiazolium-olate and diazolium-olate dipoles, as unveiled by its dipolar cycloadditions. This chameleonic reactivity has been thoroughly interpreted by dissecting the mechanistic landscape aided by the distortion–interaction model.

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REVISED-Ms-OB-COM-05-2018-001195 - Accepted Manuscript
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Accepted/In Press date: 6 June 2018
e-pub ahead of print date: 6 June 2018

Identifiers

Local EPrints ID: 422118
URI: http://eprints.soton.ac.uk/id/eprint/422118
DOI: doi:10.1039/C8OB01195H
ISSN: 1477-0520
PURE UUID: 81088857-34b4-4531-a007-a5983cc5334d
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 17 Jul 2018 16:30
Last modified: 16 Mar 2024 06:49

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Contributors

Author: Juan García de la Concepción
Author: Martín Ávalos
Author: Pedro Cintas
Author: Jose Jimenez
Author: Mark Light ORCID iD

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