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1 Oxathiirane Peter R. Schreiner, a * Hans Peter Reisenauer, a Jaroslaw Romanski, b and Grzegorz Mloston b * a Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, Giessen, Germany and b University of Lodz, Section of Heteroorganic Compounds, Tamka 12, PL Lodz, Poland Supplementary Information 1. Spectroscopic Data Figure S1. UV-spectrum of the matrix-isolated pyrolysate of 1,3-dithietan-1,3-dioxide (Ar, 10 K); dashed line: after 25 min irradiation with λ = 313 nm S1
2 H 2 C S O 2 h ν λ = 313 nm Ar, 11 K H H 1 S O + 3, 6, 7, H 2 CO, COS, HOH CS, COS, CO Figure S2. IR spectrum of the photolysis products of matrix isolated sulfine (2) in solid argon (11 K). The spectrum is obtained by subtracting the spectrum of the non-irradiated matrix from that of the irradiated matrix (1 h, 313 ± 10 nm). Positive bands: products, negative band: sulfine (2) S2
3 Figure S3. Photolysis of matrix isolated HOH CS complex in solid argon (11 K) with l = 254 nm. The spectrum is obtained by subtracting the spectrum before and after irradiation with λ = 254 nm (10 min). Positive bands: products, negative bands: HOH CS complex; lower part: computed IR spectrum of the complex (CCSD(T)/cc-pVTZ). S3
4 2. Tables of observed and computed IR data Table S1. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of oxathiirane (1) Approx. Mode Computation Experiment ν 7 a CH 2 asym. str (6.7) (vw) ν 1 a CH 2 sym. str (17.7) (w) ν 2 a CH 2 sciss (2.6) n.o. ν 3 a CH 2 wag. + ring def (25.1) (s) ν 8 a CH 2 rock (1.4) (vw) ν 4 a Ring def + CH 2 wag (5.4) (m) ν 9 a CH 2 twist (0.6) (vw) ν 5 a Ring def (29.7) (s) ν 6 a Ring def (1.5) n.o. Table S2. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of [d 2 ]-oxathiirane ([d 2 ]-1) Approx. Mode Computation Experiment ν 7 a CD 2 asym. str (5.9) (vw) ν 1 a CD 2 sym. str (13.0) (w) ν 2 a CD 2 sciss. + ring def (11.3) (m) ν 3 a CD 2 sciss.+ ring def (10.4) (s) ν 4 a CD 2 wag (7.7) (m) ν 8 a CD 2 rock (2.1) (w) ) ν 5 a ring def (24.0) (s) ν 9 a CD 2 twist (0.3) n.o. ν 6 a ring def (1.5) n.o. S4
5 Table S3. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of the H 2 O CS complex. Approx. Mode Computation Experiment ν 1 a OH 2 asym. str (124.7) (m) ν 2 a OH 2 sym. str (194.8) (vs) ν 3 a OH 2 sciss (57.6) (w) ν 4 a CS str (57.9) (s) ν 8 a CHO o.o.p. bend (94.1) n.o. ν 5 a CHO i.p. bend (75.8) n.o. ν 6 a SC HOH str (1.3) n.o. ν 7 a SCH i.p. bend (4.9) n.o. ν 9 a SCH o.o.p. bend (4.2) n.o. Table S4. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of the D 2 O CS complex. Approx. Mode Computation Experiment ν 1 a OD 2 asym. str (88.4) (s, broad) ν 2 a OD 2 sym. str (88.1) (vs) ν 3 a CS str (57.8) (s) ν 4 a OD 2 sciss (29.9) n.o. ν 8 a CDO o.o.p. bend (56.0) n.o. ν 5 a CDO i.p. bend (37.6) n.o. ν 6 a SCD i.p. bend (5.8) n.o. ν 7 a SC DOD str (1.1) n.o. ν 9 a SCD o.o.p. bend (54.6) n.o. S5
6 Table S5. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of Z-methanoic O-acid (Z-7) Approx. Mode Computation Experiment ν 1 a OH str (53.0) (w) ν 2 a CH str (7.7) n.o. ν 3 a HOC + HCO i.p (209.3) (s) bend.+ CS str. ν 4 a CO str (111.6) (m) ν 5 a HOC + HCO i.p. bend (233.3) (s) ν 8 a HC o.o.p. bend (41.4) n.o. ν 6 a CS str (23.4) n.o. ν 9 a HO o.o.p. bend (72.7) (w) ν 7 a SCO i.p. bend (15.2) n.o. Table S6. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of [d 2 ]-Z-methanoic O-acid ([d 2 ]- Z-7) Approx. Mode Computation Experiment ν 1 a OD str (30.7) n.o. ν 2 a CD str (7.4) n.o. ν 3 a OCS asym.str (439.9) (vs) ν 4 a OCS sym.str (1.9) n.o. ν 5 a DOC + DCO i.p (59.9) (w) bend ν 6 a CS str (5.7) (vw) ν 8 a DC o.o.p. bend (8.9) n.o. ν 9 a DO o.o.p. bend (50.2) (w) ν 7 a SCO i.p. bend (16.4) n.o. S6
7 Table S7. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of E-methanoic O-acid (E-7) Approx. Mode Computation Experiment ν 1 a OH str (92.0) n.o. ν 2 a CH str (22.5) n.o. ν 3 a HOC + HCO i.p (92.2) n.o. bend.+ CS str. ν 4 a HOC + HCO i.p. bend (9.2) n.o. ν 5 a CO str (449.8) n.o. ν 6 a CS str (9.7) n.o. ν 8 a HC o.o.p. bend (7.9) n.o. ν 9 a HO o.o.p. bend (111.2) n.o. ν 7 a SCO i.p. bend (4.6) n.o. S7
8 Table S8. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of Z-methanoic S-acid (Z-6) Approx. Mode Computation Experiment (Ar, 10 K) Experiment (Gas) a) ν 1 a CH str (55.5) n.o ν 2 a SH str (1.6) n.o ν 3 a CO str.r (269.1) (vs) ν 4 a HCO i.p. bend (12.9) n.o ν 8 a HC o.o.p. bend (3.7) n.o ν 5 a HSC i.p. bend (46.2) (m) ν 6 a CS str (105.9) (m) ν 7 a SCO i.p. bend (9.7) n.o ν 9 a HS o.o.p. bend (25.1) n.o a) B. P. Winnewisser, W. H. Hocking, J. Phys. Chem. 1980, 84, Table S9. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of [d 2 ]-Z-methanoic S-acid ([d 2 ]- Z-6) Approx. Mode Computation Experiment (Ar, 10 K) ν 1 a CD str (40.7) n.o. ν 2 a SD str (0.8) n.o. ν 3 a CO str.r (277.3) (vs) ν 4 a DCO i.p. bend (40.4) (s) ν 8 a DC o.o.p. bend (0.3) n.o. ν 5 a DSC i.p. bend. + CS str (65.1) (s) ν 6 a CS str. + DSC i.p. bend (41.7) (m) ν 7 a SCO i.p. bend (11.6) n.o. ν 9 a DS o.o.p. bend (16.6) n.o. S8
9 Table S10. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of E-methanoic S-acid (E-6) Approx. Mode Computation Exp. (Ar, 10 K) Exp. (Gas) a) ν 1 a CH str (56.5) n.o ν 2 a SH str (0.4) n.o ν 3 a CO str.r (303.2) (vs) ν 4 a HCO i.p. bend (21.6) n.o ν 5 a HSC i.p. bend (52.6) (m) ν 8 a HC o.o.p. bend (2.9) n.o ν 6 a CS str (77.8) (m) ν 7 a SCO i.p. bend (3.7) n.o ν 9 a HS o.o.p. bend (2.5) n.o a) B. P. Winnewisser, W. H. Hocking, J. Phys. Chem. 1980, 84, Table S11. Experimental (Ar matrix, 10 K) and computed (CCSD(T))/cc-pVTZ, intensities (km/mol) in parentheses) IR spectrum of [d 2 ]-E-methanoic S-acid ([d 2 ]-E-6) Approx. Mode Computation Exp. (Ar, 10 K) ν 1 a CD str n.o. ν 2 a SD str n.o. ν 3 a CO str.r (vs) ν 4 a DCO i.p. bend (s) ν 8 a DC o.o.p. bend n.o. ν 5 a DSC i.p. bend. + CS str (s) ν 6 a CS str. + DSC i.p. bend (m) ν 7 a SCO i.p. bend n.o. ν 9 a DS o.o.p. bend n.o. S9
10 3. Computational Results (CCSD(T)/cc-pVTZ) All coupled cluster computations were performed with the ACES2 or Cfour program: ACES2 J.F. Stanton, J. Gauss, J.D. Watts, P.G. Szalay, R.J. Bartlett with contributions from A.A. Auer, D.E. Bernholdt, O. Christiansen, M.E. Harding, M. Heckert, O. Heun, C. Huber, D. Jonsson, J. Jusélius, W.J. Lauderdale, T. Metzroth, C. Michauk, D.P. O'Neill, D.R. Price, K. Ruud, F. Schiffmann, M.E. Varner, J. Vázquez and the integral packages MOLECULE (J. Almlöf and P.R. Taylor), PROPS (P.R. Taylor), and ABACUS (T. Helgaker, H.J. Aa. Jensen, P. Jørgensen, and J. Olsen). For the current version, see CFOUR J.F. Stanton, J. Gauss, M.E. Harding, P.G. Szalay with contributions from A.A. Auer, R.J. Bartlett, U. Benedikt, C. Berger, D.E. Bernholdt, Y.J. Bomble, O. Christiansen, M. Heckert, O. Heun, C. Huber, T.-C. Jagau, D. Jonsson, J. Jusélius, K. Klein, W.J. Lauderdale, D.A. Matthews, T. Metzroth, D.P. O'Neill, D.R. Price, E. Prochnow, K. Ruud, F. Schiffmann, S. Stopkowicz, A. Tajti, J. Vázquez, F. Wang, J.D. Watts and the integral packages MOLECULE (J. Almlöf and P.R. Taylor), PROPS (P.R. Taylor), ABACUS (T. Helgaker, H.J. Aa. Jensen, P. Jørgensen, and J. Olsen), and ECP routines by A. V. Mitin and C. van Wüllen. For the current version, see S10
11 xyz-coordinates, energies, ZPVEs, and vibrational frequencies of all CCSD(T)/cc-pVTZ optimized geometries Oxathiirane Symmetry: Cs, CCSD(T) = Hartree, ZPVE = kcal/mol S C O H H Vibrations (sym. species, frequency (cm -1 ), intensity (km mol -1 )): A' A' A'' A' A'' A' A' A' A'' Thioformaldehyde-S-oxide (Sulfine) Symmetry: Cs, Energy (Hartree): , ZPVE (kcal mol -1 ): 18.3 Cartesian coordinates (Å): O S C H H S11
12 Vibrations (sym. species, frequency (cm -1 ), intensity (km mol -1 )): A' A'' A'' A' A' A' A' A' A' Trans,trans-Hydroxysulfaacetylen (HOSCH)(3): Symmetry: Cs, Energy (Hartree): ZPVE (kcal mol -1 ): 17.3 Cartesian coordinates (Å): H O S C H A'' A' A' A' A'' A' A' A' A' S12
13 trans,cis-hydroxysulfaacetylen (HOSCH)(3): Symmetry: Cs, Energy (Hartree): , ZPVE (kcal mol -1 ): 17.2 Cartesian coordinates (Å): H O S C H Vibrations (sym. species, frequency (cm -1 ), intensity (km mol -1 )): A' VIBRATION A'' VIBRATION A' VIBRATION A'' VIBRATION A' VIBRATION A' VIBRATION A' VIBRATION A' VIBRATION A' VIBRATION cis,trans-hydroxysulfaacetylen (HOSCH)(3): Symmstry: Cs, Energy (Hartree): , ZPVE (kcal mol -1 ): 17.2 Cartesian coordinates (Å): H O S C H S13
14 A'' A' A' A' A'' A' A' A' A' cis,cis-hydroxysulfaacetylen (HOSCH)(3): Symmetry: Cs, Energy (Hartree): , ZPVE (kcal mol -1 ): 17.2 Cartesian coordinates (Å): H O S C H A'' A' A' A' A'' A' A' S14
15 A' A' Trans,trans-Hydroxymercaptocarbene (HOCSH)(5) Symmetry: Cs, Energy (Hartree): , ZPVE (kcal mol -1 ): 17.8 Cartesian coordinates (Å): H O C S H A' A'' A'' A' A' A' A' A' A' Trans,cis-Hydroxymercaptocarbene (HOCSH)(5) Symmetry: Cs, Energy (Hartree): , ZPVE (kcal mol -1 ): 17.3 Cartesian coordinates (Å): H O C S H S15
16 A' A'' A' A'' A' A' A' A' A' cis,trans-hydroxymercaptocarbene (HOCSH)(5) Symmetry: Cs, Energy (Hartree): , ZPVE (kcal mol -1 ): 17.5 Cartesian coordinates (Å): H O C S H A' A'' A' A'' A' A' S16
17 A' A' A' cis,cis-hydroxymercaptocarbene (HOCSH)(5) Symmetry: Cs, Energy (Hartree): ZPVE (kcal mol -1 ): 17.0 Cartesian coordinates (Å): H O C S H A' A'' A' A'' A' A' A' A' A' Z-Methanethioic O-acid (Z-7) Symmetry: Cs, Energy = Hartrees, ZPVE = 17.7 kcal/mol Cartesian coordinates: S C O H H S17
18 A' A'' A' A'' A' A' A' A' A' E-Methanethioic O-acid (E-7) Symmetry: Cs, Energy = , ZPVE = kcal/mol Cartesian coordinates: S C O H H A' A'' A'' S18
19 A' A' A' A' A' A' Z-Methanethioic S-acid (Z-6) Symmetry: Cs, CCSD(T) = ZPVE = kcal/mol Cartesian coordinates: O C S H H A'' A' A' A' A'' A' A' A' A' E-Methanethioic S-acid (E-6) Symmetry: Cs, CCSD(T) = , ZVPE = kcal/mol Cartesian coordinates: O C S H H S19
20 A'' A' A' A'' A' A' A' A' A' Formaldehyde O-sulfide Symmetry: Cs, CCSD(T) = , ZPVE = kcal/mol Cartesian coordinates: S O C H H A'' A' A' A' A' A' Complex H2O CS Symmetry: Cs, CCSD(T) = , ZPVE = kcal/mol S20
21 Cartesian coordinates: S C H O H A'' A' A' A' A'' A' A' A' A' Formaldehyde Symmetry: C2v, CCSD(T) = , ZPVE = kcal/mol Cartesian coordinates: O C H H B B A A A B S21
22 Thioformaldehyde Symmetry: C 2v, Energy = hartree, ZPVE = 15.8 kcal mol -1 Cartesian Coordinates (Å): S C H H B A B A A B Dioxirane Point group: C 2v, Energy = hartree, ZPVE = 20.7 kcal mol -1 Cartesian Coordinates (Å): C O O H H S22
23 A B A B A B A A B Formaldehyde O-oxide Symmetry: Cs, Energy = hartree, ZPVE = 17.8 kcal mol -1 Cartesian Coordinates (Å): H C H O O Carbon monosulfide (CS) Energy (Hartree): , ZPVE (kcal mol -1 ): 1.8 Cartesian coordinates (Å): C S SG S23
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