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Inverse design of molecules with optimal reactivity properties: acidity of 2-naphthol derivatives.

Publication ,  Journal Article
De Vleeschouwer, F; Yang, W; Beratan, DN; Geerlings, P; De Proft, F
Published in: Physical chemistry chemical physics : PCCP
December 2012

The design of molecules with optimal properties is an important challenge in chemistry because of the astronomically large number of possible stable structures that is accessible in chemical space. This obstacle can be overcome through inverse molecular design. In inverse design, one uses the computation of certain indices to design molecules with an optimal target property. In this study, for the first time, inverse design was used to optimize reactivity properties of molecules. Specifically, we optimized the acidity of substituted 2-naphthols, both in the ground and the excited state. Substituted 2-naphthols belong to the class of photoacids, showing enhanced acidity when excited from the singlet ground state to the first singlet excited state. The focus of this work is the ground state. As a measure of acidity, three different properties are optimized: the charge on the hydroxyl hydrogen atom of the acid, the charge on the negatively charged oxygen atom of the conjugate base and the energy difference between acid and conjugate base. Both the practical use of the methodology and the results for ground and excited states are discussed.

Duke Scholars

Published In

Physical chemistry chemical physics : PCCP

DOI

EISSN

1463-9084

ISSN

1463-9076

Publication Date

December 2012

Volume

14

Issue

46

Start / End Page

16002 / 16013

Related Subject Headings

  • Naphthols
  • Models, Chemical
  • Hydrogen-Ion Concentration
  • Drug Design
  • Computer Simulation
  • Combinatorial Chemistry Techniques
  • Chemical Physics
  • 51 Physical sciences
  • 40 Engineering
  • 34 Chemical sciences
 

Citation

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De Vleeschouwer, F., Yang, W., Beratan, D. N., Geerlings, P., & De Proft, F. (2012). Inverse design of molecules with optimal reactivity properties: acidity of 2-naphthol derivatives. Physical Chemistry Chemical Physics : PCCP, 14(46), 16002–16013. https://doi.org/10.1039/c2cp42623d
De Vleeschouwer, Freija, Weitao Yang, David N. Beratan, Paul Geerlings, and Frank De Proft. “Inverse design of molecules with optimal reactivity properties: acidity of 2-naphthol derivatives.Physical Chemistry Chemical Physics : PCCP 14, no. 46 (December 2012): 16002–13. https://doi.org/10.1039/c2cp42623d.
De Vleeschouwer F, Yang W, Beratan DN, Geerlings P, De Proft F. Inverse design of molecules with optimal reactivity properties: acidity of 2-naphthol derivatives. Physical chemistry chemical physics : PCCP. 2012 Dec;14(46):16002–13.
De Vleeschouwer, Freija, et al. “Inverse design of molecules with optimal reactivity properties: acidity of 2-naphthol derivatives.Physical Chemistry Chemical Physics : PCCP, vol. 14, no. 46, Dec. 2012, pp. 16002–13. Epmc, doi:10.1039/c2cp42623d.
De Vleeschouwer F, Yang W, Beratan DN, Geerlings P, De Proft F. Inverse design of molecules with optimal reactivity properties: acidity of 2-naphthol derivatives. Physical chemistry chemical physics : PCCP. 2012 Dec;14(46):16002–16013.
Journal cover image

Published In

Physical chemistry chemical physics : PCCP

DOI

EISSN

1463-9084

ISSN

1463-9076

Publication Date

December 2012

Volume

14

Issue

46

Start / End Page

16002 / 16013

Related Subject Headings

  • Naphthols
  • Models, Chemical
  • Hydrogen-Ion Concentration
  • Drug Design
  • Computer Simulation
  • Combinatorial Chemistry Techniques
  • Chemical Physics
  • 51 Physical sciences
  • 40 Engineering
  • 34 Chemical sciences