Journal of Inorganic and General Chemistry
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
vacuum. After 12 h, [CH3SO2NX3]+[SbF6]– (X = H, D), was obtained
Table 3. Crystal data and structure refinement for CH3SO2NH2 and
[CH3SO2NH3]+[Sb2F11]–.
as a colorless solid. The synthesis of [CH3SO2NH3]+[Sb2F11]– was car-
ried out by the reaction of 9 equiv. of SbF5 under analogous conditions.
The obtained colorless salts are stable up to room temperature.
CH3SO2NH2
[CH3SO2NH3]+[Sb2F11]–
Mr
95.12
orthorhombic
Pnma
9.9598(5)
7.4262(4)
5.3555(3)
90
548.63
monoclinic
P21/c
7.7391(3)
9.8130(3)
15.8449(6)
90
Crystal system
Space group
a /Å
b /Å
c /Å
Acknowledgements
Financial support of this work by the Ludwig-Maximilian-University
Munich (LMU) by the Deutsche Forschungsgemeinschaft (DFG) and
F-Select GmbH is gratefully acknowledged.
α /°
β /°
90
90
396.11(4)
4
1.595
0.637
0.71073
200
173(2)
–9:12; –9:8; –6:5
1518
96.024(4)
90
1196.68(7)
4
3.045
4.826
0.71073
1008
173(2)
–4:9; –12:11; –19:18
5947
2335
0.0252
165
γ /°
V /Å3
Keywords: Methanesulfonamide; Protonation; Superacid
chemistry; Vibrational spectroscopy; X-ray diffraction
Z
ρcalcd, /g·cm–3
μ /mm–1
λ(Mo-Kα) /Å
F(000)
References
T /K
hkl range
Refl. measured
Refl. unique
Rint
[1] V. Padmavathi, P. Thriveni, G. Sudhakar Reddy, D. Deepti, Eur.
J. Med. Chem. 2008, 43, 917–924.
[2] G. L. Grunewald, M. R. Seim, R. C. Regier, J. L. Martin, C. L.
Gee, N. Drinkwater, K. R. Criscione, J. Med. Chem. 2006, 49,
5424–5433.
[3] H. LeMaire, H. J. Lucas, J. Am. Chem. Soc. 1951, 73, 5198–5201.
[4] R. G. Laughlin, J. Am. Chem. Soc. 1967, 89, 4268–4271.
[5] A. Bagno, B. Bujnicki, S. Bertrand, C. Comuzzi, F. Dorigo, P.
Janvier, G. Scorrano, Chem. Eur. J. 1999, 5, 523–536.
[6] B. A. Shainyan, N. N. Chipanina, L. P. Oznobikhina, J. Phys. Org.
Chem. 2012, 25, 738–747.
[7] L. G. Vorontsova, J. Struct. Chem. 1966, 7, 275–277.
[8] J. Weidlein, U. Müller, K. Dehnicke, Schwingungsspektroskopie,
2nd ed., Georg Thieme Verlag, Stuttgart, Germany 1988, p. 30.
[9] A. Blaschette, H. Bürger, Z. Anorg. Allg. Chem. 1970, 378, 104–
116.
439
0.0284
39
Parameters
R(F)/wR(F2)
0.0338
0.0359
a)
(all reflexions)
Weighting scheme
S(GoF)c)
b)
0.0502/0.0727
1.145
0.390/–0.336
0.0071/12.9881
1.240
1.151/–0.720
Residual density
/e·Å–3
Device type
Solution/refinement SHELXS-97
SHELXL-97
Oxford XCalibur
Oxford XCalibur
SHELXS-97
SHELXL-97
[21]
[21]
,
,
[14]
[14]
2
2 2
a) R1 = Σ||Fo|–|Fc||/Σ|Fo|. b) wR2 = [Σ[w(Fo –Fc ) ]/Σ[w(Fo)2]]1/2; w =
[σc (Fo )+(xP)2+yP]–1; P = (Fo + 2Fc )/3. c) GoF = {Σ[w(Fo –Fc ) ]/
(n–p)}1/2 (n = number of reflexions; p = total number of parameters).
2
2
2
2
2
2 2
[10] L. M. Lyapalo, H.-U. Reissig, A. Schäfer, A. Wagner, Helv. Chim.
Acta 2002, 85, 4206–4215.
[11] S. Seidel, K. Seppelt, Angew. Chem. Int. Ed. 2001, 40, 4225–
1555585 (for CH3SO2NH2) (Fax: +44-1223-336-033; E-Mail:
deposit@ccdc.cam.ac.uk, http://www.ccdc.cam.ac.uk).
4227.
[12] G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford Uni-
versity Press, Oxford, UK 1997.
Synthesis of [CH3SO2NX3]+[AsF6]– (X = H, D). Anhydrous hydrogen
fluoride, HF, (ca. 2 mL) or deuterium fluoride, DF, (ca. 2 mL) and
arsenic pentafluoride, AsF5, (1.10 mmol, 187 mg) were condensed at
–196 °C into a reactor (FEP tube). The mixture was allowed to warm
up to 0 °C to mix the components and form the superacid system.
Methanesulfonamide, CH3SO2NH2, (95 mg, 1.00 mmol) or its isotopo-
mere, CH3SO2ND2, (98 mg, 1.00 mmol) were added in an inert nitro-
gen atmosphere at –196 °C. The mixture was warmed to –50 °C for
10 min. A colorless perticipate was formed. Afterwards the reactor was
cooled to –78 °C. Excess anhydrous hydrogen fluoride (or deuterium
fluoride) and arsenic pentafluoride were removed in dynamic vacuum.
After 12 h, [CH3SO2NH3]+[AsF6]– (or [CH3SO2ND3]+[AsF6]–) was
obtained as colorless solid. The moisture sensitive salts are stable up
to room temperature.
[13] F. Belaj, C. Kratky, E. Nachbaur, A. Popitsch, Monatsh. Chem.
1987, 118, 427–433.
[14] D. E. Sands, Z. Kristallogr. 1963, 119, 245–251.
[15] T. Soltner, N. R. Goetz, A. Kornath, Eur. J. Inorg. Chem. 2011,
20, 3076–3081.
[16] J. Axhausen, C. Ritter, A. Kornath, Z. Anorg. Allg. Chem. 2013,
639, 65–72.
[17] CrysAlisCCD, Version 1.171.35.11 (release 16–05–2011 CrysAlis
171.NET), Oxford Diffraction Ltd., UK, 2011.
[18] CrysAlisRED, Version 1.171.35.11 (release 16–05–2011 CrysAlis
171.NET), Oxford Diffraction Ltd., UK, 2011.
[19] G. M. Sheldrick, SHELXS-97, Program for Crystal Structure
Solution, University of Göttingen, Germany, 1997.
[20] G. M. Sheldrick, SHELXL-97, Program for the Refinement of
Crystal Structures, University of Göttingen, Germany, 1997.
[21] L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837–838.
Synthesis of [CH3SO2NX3]+[SbF6]– (X
=
H, D) and [22] A. L. Spek, PLATON, A Multipurpose Crystallographic Tool,
[CH3SO2NH3]+[Sb2F11]–: Antimony pentafluoride, SbF5, (0.35 mmol,
76 mg), and anhydrous hydrogen fluoride (ca. 2 mL) were condensed
into a reactor (FEP tube) at –196 °C. The reactor was warmed for
10 min to 0 °C to allow the mixture of the components and form the
superacid system. Methanesulfonamide, CH3SO2NH2, (0.35 mmol,
33 mg), or its isotopomere, CH3SO2ND2, (0.35 mmol, 34 mg) were
added in an inert nitrogen atmosphere at – 196 °C. The mixture was
warmed to –50 °C for 10 min. Afterwards the reactor was cooled to
–78 °C. Excess anhydrous hydrogen fluoride was removed in dynamic
Utrecht University, Utrecht, The Netherlands, 1999.
[23] SCALE3 ABSPACK, an Oxford Diffraction Program, Oxford Dif-
fraction Ltd., UK, 2005.
[24] G. W. T. M. J. Frisch, H. B. Schlegel, G. E. Scuseria, M. A. Robb,
J. R. Cheeseman, J. A. Montgomery, T. V. K. N. Kudin Jr., J. C.
Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B.
Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H.
Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hase-
gawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M.
Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo,
Z. Anorg. Allg. Chem. 0000, 0–0
5
© 0000 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim