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Issue 23, 2010

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

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Abstract

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.

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

Supplementary files

Article information


Submitted
12 Jul 2010
Accepted
23 Aug 2010
First published
27 Sep 2010

Org. Biomol. Chem., 2010,8, 5367-5374
Article type
Paper

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

D. Cantillo, M. Ávalos, R. Babiano, P. Cintas, J. L. Jiménez, M. E. Light, J. C. Palacios and V. Rodríguez, Org. Biomol. Chem., 2010, 8, 5367 DOI: 10.1039/C0OB00416B

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