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Push-pull 1,3-thiazolium-5-thiolates. Formation via concerted and stepwise pathways, and theoretical evaluation of NLO properties

Record type: Article

The transformation of münchnones (mesoionic rings featuring the 1,3-oxazolium-5-olate core) into their sulfur counterparts (1,3-thiazolium-5-thiolates) by reaction with CS2, pioneered by Huisgen and his group in the early 1970s, has been re-investigated in detail by means of both experimental and theoretical methods. The synthetic strategy can be tuned to incorporate donor and acceptor groups in appropriate positions. Calculations of molecular hyperpolarizabilities together with orbital topologies evidence that these sulfur-containing heterocycles exhibit nonlinear optical responses, thereby pointing to potential applications of mesoionic structures in the NLO field. From a mechanistic viewpoint, modeling of the whole systems at the B3LYP/6-31G(d) level reveals that concerted and stepwise pathways are operative depending on the substitution pattern of the parent münchnone, which also account for the experimental results.


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Citation

Cantillo, David, Ávalos, Martín, Babiano, Reyes, Cintas, Pedro, Jiménez, José L., Light, Mark E., Palacios, Juan C. and Rodríguez, Valentín (2010) Push-pull 1,3-thiazolium-5-thiolates. Formation via concerted and stepwise pathways, and theoretical evaluation of NLO properties Organic and Biomolecular Chemistry, 8, (23), pp. 5367-5374. (doi:10.1039/c0ob00416b). (PMID:20871910).

More information

Published date: 2010

Identifiers

Local EPrints ID: 179405
URI: http://eprints.soton.ac.uk/id/eprint/179405
ISSN: 1477-0520
PURE UUID: 6211daa5-dd97-49bb-8bc0-6ee2432dd577
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 05 Apr 2011 08:24
Last modified: 18 Jul 2017 12:03

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Contributors

Author: David Cantillo
Author: Martín Ávalos
Author: Reyes Babiano
Author: Pedro Cintas
Author: José L. Jiménez
Author: Mark E. Light ORCID iD
Author: Juan C. Palacios
Author: Valentín Rodríguez

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