PMID- 32930587
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20210210
LR  - 20210210
IS  - 1520-5207 (Electronic)
IS  - 1520-5207 (Linking)
VI  - 124
IP  - 40
DP  - 2020 Oct 8
TI  - Insights into the Stabilization of Fluoride Ions in Ionic Liquids: Pointers to 
      Better Fluorinating Agents.
PG  - 8844-8856
LID - 10.1021/acs.jpcb.0c04939 [doi]
AB  - The fluorination efficiency of a fluorinating agent depends on the free 
      availability of the fluoride ions, which in turn depends on its interaction with 
      its solvation shell. A stable fluoride-based poor solvate ionic liquid (SIL) 
      comprising 1-ethyl-3-methylimidazolium (EMIM) cation and ethylene glycol (EG) was 
      recently reported and demonstrated as a fluorinating agent. Herein, we performed 
      ab initio calculations and ab initio molecular dynamics simulations to gain a 
      microscopic understanding of the intermolecular interactions in this SIL in gas, 
      liquid, and crystalline phases. Ethylene glycol (EG), being capable of forming 
      hydrogen bond(s) with the fluoride ion, prevents the latter from reacting with 
      the EMIM cation. Fluoride forms hydrogen bonds with both the cation and the EG 
      molecule, but it was found to have more affinity toward EG, forming a stronger 
      hydrogen bond with its hydroxyl proton than with the acidic proton of the cation. 
      An optimal concentration of EG in the SIL balances its contribution to 
      stabilizing the fluoride ion and yet making fluoride available for fluorination.
FAU - Gaur, Anjali
AU  - Gaur A
AD  - Chemistry and Physics of Materials Unit, Jawaharlal Nehru Centre for Advanced 
      Scientific Research, Bangalore 560 064, India.
FAU - Avula, Nikhil V S
AU  - Avula NVS
AD  - Chemistry and Physics of Materials Unit, Jawaharlal Nehru Centre for Advanced 
      Scientific Research, Bangalore 560 064, India.
FAU - Balasubramanian, Sundaram
AU  - Balasubramanian S
AUID- ORCID: 0000-0002-3355-6764
AD  - Chemistry and Physics of Materials Unit, Jawaharlal Nehru Centre for Advanced 
      Scientific Research, Bangalore 560 064, India.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20200929
PL  - United States
TA  - J Phys Chem B
JT  - The journal of physical chemistry. B
JID - 101157530
SB  - IM
EDAT- 2020/09/16 06:00
MHDA- 2020/09/16 06:01
CRDT- 2020/09/15 12:13
PHST- 2020/09/16 06:00 [pubmed]
PHST- 2020/09/16 06:01 [medline]
PHST- 2020/09/15 12:13 [entrez]
AID - 10.1021/acs.jpcb.0c04939 [doi]
PST - ppublish
SO  - J Phys Chem B. 2020 Oct 8;124(40):8844-8856. doi: 10.1021/acs.jpcb.0c04939. Epub 
      2020 Sep 29.