Is a methyl group always hydrophobic? Hydrophilicity of trimethylamine-N-oxide, tetramethyl urea and tetramethylammonium ion

J Phys Chem B. 2011 Mar 31;115(12):2995-3002. doi: 10.1021/jp108347b. Epub 2011 Mar 9.

Abstract

We have developed what we call the 1-propanol(1P) probing methodology. By using it, we determined the relative hydrophobicity/hydrophilicity indices of 2-butoxyethanol, a typical hydrophobe; urea, a typical hydrophile; and trimethylamine-N-oxide, an amphiphile. By comparing these indices with those for other solutes studied earlier, including tetramethyl urea, tetramethylammonium ion, mono-ols, and polyols, we suggest that methyl groups attached to an N atom, or N-methyl groups, do not promote hydrophobicity but, rather, enhance hydrophilicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Propanol / chemistry
  • Hydrophobic and Hydrophilic Interactions*
  • Methylamines / chemistry*
  • Methylurea Compounds / chemistry*
  • Quaternary Ammonium Compounds / chemistry*
  • Thermodynamics
  • Water / chemistry

Substances

  • Methylamines
  • Methylurea Compounds
  • Quaternary Ammonium Compounds
  • Water
  • 1,1,3,3-tetramethylurea
  • 1-Propanol
  • trimethyloxamine
  • tetramethylammonium