Is there hydrogen bonding for gas phase SN2 pre-reaction complexes?

Jing Xie, Jiaxu Zhang, William L. Hase

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Abstract For some gas-phase X- + CH3Y → XCH3 + Y- SN2 nucleophilic substitution reactions a pre-reaction complex is formed in which the attacking anion binds to a H-atom to form X-⋯HCH2Y. In this work properties of this complex are investigated, for the OH- + CH3I and F- + CH3I reactions, to determine whether the HO-⋯HCH2I and F-⋯HCH2I complexes should be considered hydrogen-bonded complexes. Properties considered for these complexes are their structures, vibrational frequencies, well depths, and partial atomic charges. Also considered is the role of the HO-⋯HCH2I complex in proton transfer for both the proton transfer and SN2 reaction pathways. The results of these analyses indicate that these X-⋯HCH2Y complexes are hydrogen bonding complexes.

Original languageEnglish
Article number15151
Pages (from-to)14-19
Number of pages6
JournalInternational Journal of Mass Spectrometry
Volume378
DOIs
StatePublished - Feb 15 2015

Keywords

  • Hydrogen bond
  • Mulliken charge
  • Pre-reaction complex
  • Proton-donor

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