The Nature of Protic Ionic Liquids in the Gas Phase Revisited: Fourier Transform Ion Cyclotron
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1 The Nature of Protic Ionic Liquids in the Gas Phase Revisited: Fourier Transform Ion Cyclotron Resonance Mass Spectrometry Study of 1,1,3,3-Tetramethylguanidinium Chloride Joana Vitorino, a,b João P. Leal, a,b Manuel E. Minas da Piedade,*,a José N. Canongia Lopes, c,d José M. S. S. Esperança, c Luís Paulo N. Rebelo c a Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Lisboa, Portugal; memp@fc.ul.pt b Unidade de Ciências Químicas e Radiofarmacêuticas, Instituto Tecnológico e Nuclear, Sacavém, Portugal. c Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Av. República, Apartado 127, Oeiras, Portugal; d Centro de Química Estrutural, Complexo Interdisciplinar, Instituto Superior Técnico da Universidade Técnica de Lisboa, Lisboa, Portugal. RECEIVED DATE (to be automatically inserted after your manuscript is accepted if required according to the journal that you are submitting your paper to) KEYWORDS: Ionic liquids / protic ionic liquids / 1,1,3,3-tetramethylguanidinium chloride / FT-ICR-MS / gas-phase reactions BRIEFS (WORD Style BH_Briefs ). Vaporization of 1,1,3,3-Tetramethylguanidinium Chloride 1
2 Supporting Information SpinWorks 2.5: MSG10 - DMSO-d6 (1H) PPM file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\DMSO-d6 (1H)\fid expt: <zg30> transmitter freq.: MHz time domain size: points width: Hz = ppm = Hz/pt number of scans: 16 freq. of 0 ppm: MHz processed size: complex points LB: GB: Figure S1. 1 H NMR spectrum of the solvent DMSO-d 6 recorded at ambient temperature. Chemical shifts are given relative to TMS. 2
3 SpinWorks 2.5: MSG20-1,1,3,3-tetrametilguanidina em DMSO-d6 (1H) PPM file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\1,1,3,3-tetrametilguanidina (1H)\fid expt: <zg30> transmitter freq.: MHz time domain size: points width: Hz = ppm = Hz/pt number of scans: 16 freq. of 0 ppm: MHz processed size: complex points LB: GB: Figure S2. 1 H NMR spectrum of tmg recorded at ambient temperature in DMSO-d 6. Chemical shifts are given relative to TMS. 3
4 SpinWorks 2.5: MSG30 - N,N,N`,N`-tetrametil-N``-1H-guanidinio cloreto em DMSO-d6 (1H) PPM file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\N,N,N',N'-tetrametil-N''-1H-guanidinio cloreto (1H)\fid expt: <zg30> freq. of 0 ppm: MHz transmitter freq.: MHz processed size: complex points time domain size: points LB: GB: width: Hz = ppm = Hz/pt number of scans: 16 Figure S3. 1 H NMR spectrum of [Htmg]Cl (sample 1) recorded at ambient temperature in DMSO-d 6. Chemical shifts are given relative to TMS. 4
5 SpinWorks 2.5: MSG11 - DMSO-d6 (13C) PPM file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\DMSO-d6 (13C)\fid expt: <jmod> transmitter freq.: MHz time domain size: points width: Hz = ppm = Hz/pt number of scans: 1000 freq. of 0 ppm: MHz processed size: complex points LB: GB: Figure S4. 13 C NMR spectrum of the solvent DMSO-d 6 recorded at ambient temperature. Chemical shifts are given relative to TMS. 5
6 SpinWorks 2.5: MSG21-1,1,3,3-tetrametilguanidina em DMSO-d6 (13C) PPM file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\1,1,3,3-tetrametilguanidina (13C)\fid expt: <jmod> transmitter freq.: MHz time domain size: points width: Hz = ppm = Hz/pt number of scans: 1000 freq. of 0 ppm: MHz processed size: complex points LB: GB: Figure S5. 13 C NMR spectrum of tmg recorded at ambient temperature in DMSO-d 6. Chemical shifts are given relative to TMS. 6
7 SpinWorks 2.5: MSG31 - N,N,N`,N`-tetrametil-N``-1H-guanidinio cloreto em DMSO-d6 (13C) PPM file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\N,N,N',N'-tetrametil-N''-1H-guanidinio cloreto (13C)\fid expt: <jmod> freq. of 0 ppm: MHz transmitter freq.: MHz processed size: complex points time domain size: points LB: GB: width: Hz = ppm = Hz/pt number of scans: 1000 Figure S6. 13 C NMR spectrum of [Htmg]Cl (sample 1) recorded at ambient temperature in DMSO-d 6. Chemical shifts are given relative to TMS. 7
8 (a) (b) Figure S7. DSC measuring curves obtained for sample 1 [Htmg]Cl (sample 1, unsublimed) at a scan rate of 10 K min -1. (a) First run; (b) second run. 8
![sample 1 [Htmg]Cl (sample 1,](/docs-images/48/18348188/images/page_8.jpg "unsublimed) at a scan rate of 10 K min")
9 (a) (b) Figure S8. DSC measuring curves obtained for sample 2 [Htmg]Cl (sample 2, sublimed) at a scan rate of 10 K min -1. (a) First run; (b) second run. 9
![sample 2 [Htmg]Cl (sample 2, sublimed)](/docs-images/48/18348188/images/page_9.jpg "at a scan rate of 10 K min -1.")
10 Figure S9. Results of the TG analysis of [Htmg]Cl (sample 1) carried out at 10 K min
![analysis of [Htmg]Cl](/docs-images/48/18348188/images/page_10.jpg "(sample 1) carried out")
11 Figure S10. Isothermal thermogravimetry results for a [Htmg]Cl sample 1 maintained at ambient pressure and 373 K. 11
![results for a [Htmg]Cl](/docs-images/48/18348188/images/page_11.jpg "sample 1 maintained at")
12 Figure S11. Isothermal thermogravimetry results for a [Htmg]Cl sample 1 maintained at ambient pressure and 423 K. 12
![results for a [Htmg]Cl](/docs-images/48/18348188/images/page_12.jpg "sample 1 maintained at")
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