The seeming lack of CFHO intramolecular hydrogen bonds in linear aliphatic fluoroalcohols in solution

R. A. Cormanich, R. Rittner, M. P. Freitas*, M. Buehl

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

No CFHO intramolecular hydrogen bonds (IHBs) in 2-fluoroethanol, 3-fluoropropanol and 4-fluorobutanol can be detected experimentally in solution by NMR and infrared spectroscopies. According to ab initio (MP2/aug-cc-pVDZ) and DFT calculations (B3LYP), a CFHO IHB has no influence on the conformational behavior of 2-fluoroethanol, while it stabilises the global minima of 3-fluoropropanol and 4-fluorobutanol for the isolated molecules. Entropy and bulk solvation effects, even in nonpolar media, such as CCl4, cyclohexane and dichloromethane, are indicated to diminish the population of these global minima, apparently below the detection limit.

Original languageEnglish
Pages (from-to)19212-19217
Number of pages6
JournalPhysical Chemistry Chemical Physics
Volume16
Issue number36
Early online date24 Jul 2014
DOIs
Publication statusPublished - 28 Sept 2014

Keywords

  • Phase electron-diffraction
  • Spin coupling-constants
  • Conformational-analysis
  • AB-initio
  • Fluorine
  • Acceptor

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