Pushing the boundaries of intrinsically stable radicals: inverse design using the thiadiazinyl radical as a template.

Published

Journal Article

In this study, for the first time inverse design was applied to search for the intrinsically most stable radical system in a predefined chemical space of enormous size by scanning in a rational way that entire chemical space. The focus was predominantly on thermodynamic stabilization effects, such as stabilization through resonance. Two different properties were optimized: a newly introduced descriptor called the radical delocalization value and the intrinsic stability via a previously established bond dissociation enthalpy model. The thiadiazinyl radical was chosen as case study of this new approach of inverse design in stable radical chemistry. The resulting optimal structure is found to be highly stable, intrinsically more so than other well-known stable radicals, such as verdazyls and N,N-diphenyl-N'-picrylhydrazyl, and even rivaling the intrinsic stability of nitrogen monoxide.

Full Text

Duke Authors

Cited Authors

  • De Vleeschouwer, F; Chankisjijev, A; Yang, W; Geerlings, P; De Proft, F

Published Date

  • April 2013

Published In

Volume / Issue

  • 78 / 7

Start / End Page

  • 3151 - 3158

PubMed ID

  • 23461465

Pubmed Central ID

  • 23461465

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo400101d

Language

  • eng