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The Nature of Protic Ionic Liquids in the Gas Phase Revisited: Fourier Transform Ion Cyclotron

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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,

1649-016 Lisboa, Portugal; E-mail: memp@fc.ul.pt

b

Unidade de Ciências Químicas e Radiofarmacêuticas, Instituto Tecnológico e Nuclear, 2686-953 Sacavém,

Portugal.

c

Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Av. República, Apartado 127,

2780-901 Oeiras, Portugal; www.itqb.unl.pt.

d

Centro de Química Estrutural, Complexo Interdisciplinar, Instituto Superior Técnico da Universidade

Técnica de Lisboa, 1049-001 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)

(2)

Supporting Information

SpinWorks 2.5: MSG10 - DMSO-d6 (1H)

PPM

8.0 7.6 7.2 6.8 6.4 6.0 5.6 5.2 4.8 4.4 4.0 3.6 3.2 2.8 2.4 2.0 1.6 1.2 0.8

0.4

3 .3 3 2 7 2 .5 2 4 6 2 .5 2 0 2 2 .5 1 5 7 2 .5 1 1 1 2 .5 0 6 7

file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\DMSO-d6 (1H)\fid expt: <zg30> transmitter freq.: 400.137471 MHz

time domain size: 65536 points

width: 8223.68 Hz = 20.552147 ppm = 0.125483 Hz/pt number of scans: 16

freq. of 0 ppm: 400.135000 MHz processed size: 32768 complex points LB: 0.000 GB: 0.0000

Figure S1.

1

H NMR spectrum of the solvent DMSO-d

6

recorded at ambient temperature. Chemical shifts

(3)

SpinWorks 2.5: MSG20 - 1,1,3,3-tetrametilguanidina em DMSO-d6 (1H)

PPM

8.0 7.6 7.2 6.8 6.4 6.0 5.6 5.2 4.8 4.4 4.0 3.6 3.2 2.8 2.4 2.0 1.6 1.2 0.8

0.4

1 2 .0 0 1 .0 2 2 5 .3 6 1 6 3 .3 5 2 3 2 .6 2 2 1 2 .5 1 9 8 2 .5 1 5 5 2 .5 1 1 3

file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\1,1,3,3-tetrametilguanidina (1H)\fid expt: <zg30> transmitter freq.: 400.137471 MHz

time domain size: 65536 points

width: 8223.68 Hz = 20.552147 ppm = 0.125483 Hz/pt number of scans: 16

freq. of 0 ppm: 400.135000 MHz processed size: 32768 complex points LB: 0.000 GB: 0.0000

Figure S2.

1

H NMR spectrum of tmg recorded at ambient temperature in DMSO-d

6

. Chemical shifts are

(4)

SpinWorks 2.5: MSG30 - N,N,N`,N`-tetrametil-N``-1H-guanidinio cloreto em DMSO-d6 (1H)

PPM

8.0 7.6 7.2 6.8 6.4 6.0 5.6 5.2 4.8 4.4 4.0 3.6 3.2 2.8 2.4 2.0 1.6 1.2 0.8

0.4

1 2 .0 0 2 .0 0 3 8 .0 2 5 5 3 .3 5 1 8 2 .9 1 0 5 2 .5 2 0 2 2 .5 1 5 9 2 .5 1 1 6

file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\N,N,N',N'-tetrametil-N''-1H-guanidinio cloreto (1H)\fid expt: <zg30> transmitter freq.: 400.137471 MHz

time domain size: 65536 points

width: 8223.68 Hz = 20.552147 ppm = 0.125483 Hz/pt number of scans: 16

freq. of 0 ppm: 400.135000 MHz processed size: 32768 complex points LB: 0.000 GB: 0.0000

Figure S3.

1

H NMR spectrum of [Htmg]Cl (sample 1) recorded at ambient temperature in DMSO-d

6

.

(5)

SpinWorks 2.5: MSG11 - DMSO-d6 (13C)

PPM

180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0

4 0 .1 2 3 0 3 9 .9 1 4 0 3 9 .7 0 5 2 3 9 .4 9 6 1 3 9 .2 8 7 0 3 9 .0 7 8 4 3 8 .8 6 8 5

file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\DMSO-d6 (13C)\fid expt: <jmod> transmitter freq.: 100.624087 MHz

time domain size: 65536 points

width: 24038.46 Hz = 238.893710 ppm = 0.366798 Hz/pt number of scans: 1000

freq. of 0 ppm: 100.614077 MHz processed size: 32768 complex points LB: 0.000 GB: 0.0000

Figure S4.

13

C NMR spectrum of the solvent DMSO-d

6

recorded at ambient temperature. Chemical shifts

(6)

SpinWorks 2.5: MSG21 - 1,1,3,3-tetrametilguanidina em DMSO-d6 (13C)

PPM

180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0

1 6 6 .1 9 7 4 4 0 .1 2 5 5 3 9 .9 1 7 0 3 9 .7 0 8 1 3 9 .4 9 9 0 3 9 .3 9 2 9 3 9 .2 9 0 3 3 9 .0 8 4 8 3 9 .0 4 9 3 3 8 .8 7 2 8

file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\1,1,3,3-tetrametilguanidina (13C)\fid expt: <jmod> transmitter freq.: 100.624087 MHz

time domain size: 65536 points

width: 24038.46 Hz = 238.893710 ppm = 0.366798 Hz/pt number of scans: 1000

freq. of 0 ppm: 100.614077 MHz processed size: 32768 complex points LB: 0.000 GB: 0.0000

Figure S5.

13

C NMR spectrum of tmg recorded at ambient temperature in DMSO-d

6

. Chemical shifts are

(7)

SpinWorks 2.5: MSG31 - N,N,N`,N`-tetrametil-N``-1H-guanidinio cloreto em DMSO-d6 (13C)

PPM

180.0 170.0 160.0 150.0 140.0 130.0 120.0 110.0 100.0 90.0 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0

1 6 0 .8 9 8 9 4 0 .1 2 4 6 3 9 .9 1 5 9 3 9 .7 0 7 1 3 9 .4 9 8 3 3 9 .4 2 6 8 3 9 .4 1 6 9 3 9 .2 8 9 5 3 9 .0 8 0 7 3 8 .8 7 1 4

file: C:\Documents and Settings\IMIDAZOLIUM-PC\Desktop\RMN\TMG Cl\N,N,N',N'-tetrametil-N''-1H-guanidinio cloreto (13C)\fid expt: <jmod> transmitter freq.: 100.624087 MHz

time domain size: 65536 points

width: 24038.46 Hz = 238.893710 ppm = 0.366798 Hz/pt number of scans: 1000

freq. of 0 ppm: 100.614077 MHz processed size: 32768 complex points LB: 0.000 GB: 0.0000

Figure S6.

13

C NMR spectrum of [Htmg]Cl (sample 1) recorded at ambient temperature in DMSO-d

6

.

(8)

(a)

(9)
(10)
(11)

Figure S10.

Isothermal thermogravimetry results for a [Htmg]Cl sample 1 maintained at ambient pressure

and 373 K.

(12)

References

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