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Acidity constant (pKa) calculation of large solvated dye molecules : evaluation of two advanced molecular dynamics methods

(2016) CHEMPHYSCHEM . 17(21). p.3447-3459
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Abstract
pH-Sensitive dyes are increasingly applied on polymer substrates for the creation of novel sensor materials. Recently, these dye molecules were modified to form a covalent bond with the polymer host. This had a large influence on the pH-sensitive properties, in particular on the acidity constant (pKa). Obtaining molecular control over the factors that influence the pK(a) value is mandatory for the future intelligent design of sensor materials. Herein, we show that advanced molecular dynamics (MD) methods have reached the level at which the pK(a) values of large solvated dye molecules can be predicted with high accuracy. Two MD methods were used in this work: steered or restrained MD and the insertion/deletion scheme. Both were first calibrated on a set of phenol derivatives and afterwards applied to the dye molecule bromothymol blue. Excellent agreement with experimental values was obtained, which opens perspectives for using these methods for designing dye molecules.
Keywords
Physical and Theoretical Chemistry, Atomic and Molecular Physics, and Optics, DENSITY-FUNCTIONAL THEORY, PH-SENSITIVE FUNCTION, TEXTILE MATERIALS, AQUEOUS-SOLUTION, LIQUID WATER, FREE-ENERGY, PKA VALUES, HALOCHROMIC PROPERTIES, SULFONPHTHALEINE DYES, NITRAZINE YELLOW

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Chicago
De Meyer, Thierry, Bernd Ensing, Sven Rogge, Karen De Clerck, Evert Jan Meijer, and Veronique Van Speybroeck. 2016. “Acidity Constant (pKa) Calculation of Large Solvated Dye Molecules : Evaluation of Two Advanced Molecular Dynamics Methods.” Chemphyschem 17 (21): 3447–3459.
APA
De Meyer, Thierry, Ensing, B., Rogge, S., De Clerck, K., Meijer, E. J., & Van Speybroeck, V. (2016). Acidity constant (pKa) calculation of large solvated dye molecules : evaluation of two advanced molecular dynamics methods. CHEMPHYSCHEM , 17(21), 3447–3459.
Vancouver
1.
De Meyer T, Ensing B, Rogge S, De Clerck K, Meijer EJ, Van Speybroeck V. Acidity constant (pKa) calculation of large solvated dye molecules : evaluation of two advanced molecular dynamics methods. CHEMPHYSCHEM . Wiley-Blackwell; 2016;17(21):3447–59.
MLA
De Meyer, Thierry, Bernd Ensing, Sven Rogge, et al. “Acidity Constant (pKa) Calculation of Large Solvated Dye Molecules : Evaluation of Two Advanced Molecular Dynamics Methods.” CHEMPHYSCHEM 17.21 (2016): 3447–3459. Print.
@article{8501546,
  abstract     = {pH-Sensitive dyes are increasingly applied on polymer substrates for the creation of novel sensor materials. Recently, these dye molecules were modified to form a covalent bond with the polymer host. This had a large influence on the pH-sensitive properties, in particular on the acidity constant (pKa). Obtaining molecular control over the factors that influence the pK(a) value is mandatory for the future intelligent design of sensor materials. Herein, we show that advanced molecular dynamics (MD) methods have reached the level at which the pK(a) values of large solvated dye molecules can be predicted with high accuracy. Two MD methods were used in this work: steered or restrained MD and the insertion/deletion scheme. Both were first calibrated on a set of phenol derivatives and afterwards applied to the dye molecule bromothymol blue. Excellent agreement with experimental values was obtained, which opens perspectives for using these methods for designing dye molecules.},
  author       = {De Meyer, Thierry and Ensing, Bernd and Rogge, Sven and De Clerck, Karen and Meijer, Evert Jan and Van Speybroeck, Veronique},
  issn         = {1439-4235},
  journal      = {CHEMPHYSCHEM },
  keyword      = {Physical and Theoretical Chemistry,Atomic and Molecular Physics,and Optics,DENSITY-FUNCTIONAL THEORY,PH-SENSITIVE FUNCTION,TEXTILE MATERIALS,AQUEOUS-SOLUTION,LIQUID WATER,FREE-ENERGY,PKA VALUES,HALOCHROMIC PROPERTIES,SULFONPHTHALEINE DYES,NITRAZINE YELLOW},
  language     = {eng},
  number       = {21},
  pages        = {3447--3459},
  publisher    = {Wiley-Blackwell},
  title        = {Acidity constant (pKa) calculation of large solvated dye molecules : evaluation of two advanced molecular dynamics methods},
  url          = {http://dx.doi.org/10.1002/cphc.201600734},
  volume       = {17},
  year         = {2016},
}

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