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1 SUPPORTING INFORMATION CO 2 -selective absorbents in air: Reverse lipid bilayer structure forming neutral carbamic acid in water without hydration Fuyuhiko Inagaki*, Chiaki Matsumoto, Takashi Iwata and Chisato Mukai Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University Kakuma-machi, Kanazawa (Japan) *Correspondence should be directed to Dr. Fuyuhiko Inagaki at finagaki@p.kanazawa-u.ac.jp S1
2 General. Infrared spectra were measured with a Thermo Fisher Scientific NICOLET is5(atr) in neat. 1 H NMR spectra were measured with JNM-ECS400 or JNM-ECA600 spectrometers for samples in chloroform-d (CDCl 3 ), and heavy water (D 2 O), using either tetramethylsilane (for compound with a phenyl group), CHCl 3 (7.26 ppm), and D 2 O (4.79 ppm) as an internal reference. 13 C NMR spectra were measured with JNM-ECS400 or JNM-ECA600 spectrometers for samples in chloroform-d (CDCl 3 ), and heavy water (D 2 O), using CDCl 3 (77.0 ppm) as an internal reference. One dimensional 13 C CP-MAS solid state NMR spectra was measured by JEOL ECA300 spectrometer operating at nad MHz resonance frequencies for 1 H and 13 C, respectively. The spinning frequency was set to 50 KHz for 1H. MAS speed was 12 khz. Elemental analysis was conducted with a J-SCIENCE LAB JM10. Concentration of CO 2 was measured with Good ability GC-02 (sealed space) or SATOTECH MCH-383SD (open space). Melting or CO 2 generating points were measured with YANAGIMOTO micro melting point apparatus, and were uncorrected. Commercially available monoethanolamine (MEA, Tokyo Chemical Industry), benzylamine (BZA, 4a, Nacalai Tesque), phenetylamine (PEA, 4b, Tokyo Chemical Industry), N-methylbenzylamine (NMBZA, 4c, Nacalai Tesque), p-methoxybenzylamine (PMBZA, 4d, KANTO Chemical), m-xylylenediamine (MXDA, 4e, Tokyo Chemical Industry), p-xylylenediamine (PXDA, 4f, Tokyo Chemical Industry), o-xylylenediamine (OXDA, 4g, Aldrich) were employed for reactions. Silica gel (Silica gel 60 N, µm, Kanto Chemical) was used for chromatography. Concentration of atmospheric CO 2 was recorded between approximately 300 and 600 ppm. All reactions were conducted under air at room temperature unless otherwise stated. S2
3 Experimental Details 1, General Procedure for CO 2 Absorption Experiment in Sealed Box S1 Amine derivative (5.0 mmol: benzylamine (BZA, 4a), phenetylamine (PEA, 4b), N-methylbenzylamine (NMBZA, 4c), p-methoxybenzylamine (PMBZA, 4d), m-xylylenediamine (MXDA, 4e), p-xylylenediamine (PXDA, 4f), and o-xylylenediamine (OXDA, 4g)) was set on the petri dish in a desiccator (35.7 L). After closing the door, the CO 2 concentration was measured by CO 2 monitor for 24 h. The results are summarized in Figure 2a and Table S1. Table S1. CO 2 Concentration in Sealed Box. S3
4 2, CO 2 Absorption Experiment on Scale S1 Amine derivatives (75 mmol; 4b,d-f) was set on the petri dish. The increment was measured with scale. The results are summarized in Figure 2b and Table S2. Table S2. Increment of x(co 2 ) y(amines) z(h 2 O) under Atmosphere. 3, CO 2 Absorption Experiment in Air S1 Amine derivative (4b,d-g) was set on the petri dish in open space, and reacted with air at room temperature. After more than 2 weeks, the products 5b,d-g were measured by elemental analysis. The results are summarized in Figure 2c and Table S3. Table S3. Elemental analysis of the product between amines 4b,d-g and air. 4(CO 2 ) 9(PEA) (H 2 O) (5b) colorless powder: Anal. Calcd for C 76 H 101 N 9 O 9 : C, 71.05; H, 7.92; N, Found: C, 70.87; H, 7.95; N, (CO 2 ) 9(PMBZA) (H 2 O) (5d) S4
5 colorless powder: Anal. Calcd for C 76 H 101 N 9 O 18 : C, 63.89; H, 7.13; N, Found: C, 64.06; H, 6.97; N, [3-(Aminomethyl)benzyl]carbamic acid (MXDA CO 2, 5e) colorless powder: solid 13 C NMR δ 165.2, 142.1, 136.6, 128.6, 45.4, IR 3338, 3033, 2993, 2909, 2870, 2632, 2200, 1662, 1597, 1541, 1415, 1368, 1321, 1246, 1186, 1160, 1082, 1032, 1003, 941, 823, 790, 729, 710, 694, 649, 619, 605, 566 cm -1, mp C (CO 2 emission). Anal. Calcd for C 9 H 12 N 2 O 2 : C, 59.99; H, 6.71; N, Found (1st): C, 60.07; H, 6.70; N, 15.64, (2nd): C, 60.10; H, 6.63; N, 6.88, (3rd): C, 60.00; H, 6.88; N, X-ray: Crystal was recrystallized in water (CCDC ). [4-(Aminomethyl)benzyl]carbamic acid (PXDA CO 2, 5f) S2 colorless powder: solid 13 C NMR δ 164.3, 140.5, 134.8, 130.2, 127.4, 46.3, IR 3336, 3021, 2954, 1900, 2863, 2137, 1662, 1596, 1490, 1452, 1434, 1384, 1283, 1227, 1211, 1143, 1034, 992, 941, 923, 898, 870, 810, 771, 743, 700, 607, 583, 462 cm -1. Temperature of CO 2 emission (5f covered with silicon oil) C. Anal. Calcd for C 9 H 12 N 2 O 2 : C, 59.99; H, 6.71; N, Found: C, 60.04; H, 7.07; N, f, which was derived from PXDA and 1 atm of CO 2 (not air), was reported by one paper in Japanese. 29 [2-(Aminomethyl)benzyl]carbamic acid (OXDA CO 2, 5g) pale yellow powder: solid 13 C NMR δ 163.4, 143.3, 136.6, 134.8, 128.8, 48.2, IR 3336, 3021, 2954, 1900, 2863, 2137, 1662, 1596, 1490, 1452, 1434, 1384, 1283, 1227, 1211, 1143, 1034, 992, 941, 923, 898, 870, 810, 771, 743, 700, 607, 583, 462 cm -1, mp C (CO 2 emission). Anal. Calcd for C 9 H 12 N 2 O 2 : C, 59.99; H, 6.71; N, Found: C, 60.25; H, 6.80; N, According to the above method, alkylamines (N-methylaminoethanol (MAE), ethylenediamine (EDA), N,N -dimethylethylenediamine (DMEDA), diethylenetriamine (DETA)) were also reacted with air at room temperature. The result is summarized in Table S4. Table S4. Elemental analysis of the product between alkylamines and air. S5
6 The ratio of x(co 2 ) y(alkylamines) z(h 2 O) was calculated as follows. (a) 0.34(CO 2 ) (MAE) (H 2 O) Elemental analysis (%) (1) C H N O Molar ratio = (1)/atomic weight 29.44/ / / /16 = : : : = ) 1 mol (= y) of MAE (C 3 H 9 NO) = x(co 2 ) z(h 2 O) ) 0.34 mol (= x) of CO = z(h 2 O) (b) 0.27(CO 2 ) (EDA) (H 2 O) : : : C H N O Elemental analysis (%) (1) Molar ratio = (1)/atomic weight 18.17/ / / /16 = = ) 1 mol (= y) of EDA (C 2 H 8 N 2 ) = x(co 2 ) z(h 2 O) ) 0.27 mol (= x) of CO = z(h 2 O) (c) 0.86(CO 2 ) (DMEDA) (H 2 O) : : : C H N O Elemental analysis (%) (1) Molar ratio = (1)/atomic weight 28.16/ / / /16 = = ) 1 mol (= y) of DMEDA (C 4 H 12 N 2 ) = x(co 2 ) z(h 2 O) ) 0.86 mol (= x) of CO = z(h 2 O) (d) 0.35(CO 2 ) (DETA) 4.8-5(H 2 O) : : : C H N O Elemental analysis (%) (1) Molar ratio = (1)/atomic weight 25.50/ / / /16 = = ) 1 mol (= y) of DETA (C 4 H 13 N 3 ) = x(co 2 ) z(h 2 O) ) 0.35 mol (= x) of CO = z(h 2 O) S6
7 4, General Procedure for Grignard Reaction with CO 2 absorbents a) Grignard Reaction with (CO 2 ) 3(MEA) 3(H 2 O) (1) (i) For generating CO 2 gas, (CO 2 ) 3(MEA) 3(H 2 O) (1, 7.5 ml, 50 mmol) S1 was heated at 120 C. (ii) To a suspension of Mg (288 mg, 12 mmol) in THF (10 ml) was added beomobenzene or bromocyclohexane (10 mmol) at room temperature under N 2 atmosphere, and the resulting mixture was heated at 50 C for 1 h. After cooling at 0 C, genareted gas from (i) was added to the mixture, and stirred for 3 h at the same temperature. The reaction mixture was quenched with aqueous NH 4 Cl and extracted with Et 2 O. The organic layer was washed with water, brine, dried with Na 2 SO 4. The residue was chromatographed with hexane-acoet-meoh (1:1:0 to 0:10:1) to afford the corresponding carboxylic acid. The results are summarized in Figure 5. b) Grignard Reaction with MXDA CO 2 (5e) (i) For generating CO 2 gas, MXDA CO 2 (5e, 9.01 g, 50 mmol) was heated at reflux in toluene. (ii) To a suspension of Mg (288 mg, 12 mmol) in THF (10 ml) was added beomobenzene or bromocyclohexane (10 mmol) at room temperature under N 2 atmosphere, and the resulting mixture was heated at 50 C for 1 h. After cooling at 0 C, genareted gas from (i) was added to the mixture, and stirred for 3 h at the same temperature. The reaction mixture was quenched with aqueous NH 4 Cl and extracted with Et 2 O. The organic layer was washed with water, brine, dried with Na 2 SO 4. The residue was chromatographed with hexane-acoet-meoh (1:1:0 to 0:10:1) to afford the corresponding carboxylic acid. The results are summarized in Figure 5. Benzoic acid (7a) IR 3071, 2981, 2827, 2665, 2604, 2551, 1680, 1601, 1582, 1453, 1420, 1323, 1288, 1180, 1127 cm -1 ; 1 H NMR δ (m, 2H), (m, 1H), (m, 2H); 13 C NMR δ 172.3, 133.8, 130.2, 129.3, Cyclohexanecarboxylic acid (7b) IR 2930, 2855, 1698, 1451, 1417, 1311, 1256, 1213, 1182, 1136 cm -1 ; 1 H NMR δ 2.31 (tt, J = 3.8, 11.3 Hz, 1H), (m, 2H), 1.74 (dt, J = 3.8, 11.3 Hz, 2H), 1.62 (dt, J = 3.8, 11.3 Hz, 1H), (m, 2H), (m, 3H); 13 C NMR δ 182.6, 42.9, 28.8, 25.7, S7
8 References S1) Inagaki, F.; Okada, Y.; Matsumoto, C.; Yamada, M.; Nakazawa, K.; Mukai, C. Chem. Pharm. Bull. 2016, 64, S2) Nishi, T.; Abe, Y., J. Synth. Org. Chem. Jpn. 1969, 27, S8
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