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1 Arkivoc 2017, v, 1-32 upplementary Material olvent-free synthesis of (poly)thiacalix[n]arenes: the evaluation of possible mechanism based on semi-preparative HPL separation and mass-spectrometric investigation of the reaction products Igor. Kovalev, a, Matiur Rahman, a, Leila K. adieva, a Dmitry E. Pavlyuk, a Kousik Giri,* c ougata antra,* a Dmitry. Kopchuk, a,b Grigory. V. Zyryanov, a,b Adinath Majee, d Oleg N. hupakhin, a,b and Valery N. harushin a,b a Department of Organic and Biomolecular hemistry, hemical Engineering Institute, Ural Federal University, 19 Mira treet, Yekaterinburg, K-2, , Russian Federation b I. Ya. Postovskiy Institute of Organic ynthesis, Ural Division of the Russian Academy of ciences, 22. Kovalevskoy tr., Yekaterinburg, , Russian Federation c entre for omputational ciences, chool of Basic and Applied ciences, entral University of Punjab, ity ampus, Mansa Road, Bathinda , India d Department of hemistry, Visva-Bharati (A entral University), antiniketan , India Dr. Igor. Kovalev and Dr. Matiur Rahman contributed equally to this article sougatasantra85@gmail.com, kousikgiri@gmail.com Page 1 ARKAT UA, Inc
2 Arkivoc 2017, v, 1-32 Method of analysis The qualitative composition of the mixture of TAs from Methods 1-2 was determined by HPL analysis on Agilent 1200 chromatograph equipped with columns Zorbax B mm (5 µm) and Zorbax B mm (5 µm), detection wavelength 254 nm. Analysis of the crude mixture of TAs (Method 2) ample preparation To the 50 mg of TAs in the 1.5 ml vial was added 700 µl DMO. Vial was sonicated on ultrasonic bath for 5 minutes. The suspension in vial was centrifuged and clear fugate was transferred to clear 1.5 ml vial. The selection of a mobile phase For the optimal condition for HPL analysis was carried out separation of the TAs mixture in isocratic mode in the following systems of solvents: I) М solution of trisodium citrate 5,5-hydrate (channel A) acetonitrile (channel В) (Table 1) Table 1 А В column Flow rate (ml/min) comment Zorbax B mm 0.5 No separation (see. Fig. 1) Zorbax B mm Zorbax B mm 0.3 Partial separation (see. Fig. 2) Zorbax B mm 0.5 No separation (see. Fig. 3) Zorbax B mm 0.5 Total separation (see. Fig. 4) Zorbax B mm Zorbax B mm Zorbax B mm Zorbax B mm Zorbax B mm Zorbax B mm 4 No separation Total separation Page 2 ARKAT UA, Inc
3 Arkivoc 2017, v, 1-32 Figure % water solution of formic acid (channel А) acetonitrile (channel В) (Table 2) Table 2 А В column Flow rate (ml/min) Zorbax B mm Zorbax B mm Zorbax B mm Zorbax B mm Zorbax B mm Zorbax B mm Zorbax B mm 0.5 comment Irreversible sorbtion of analites (see. Fig. 5) Page 3 ARKAT UA, Inc
4 Arkivoc 2017, v, 1-32 Figure М solution of ammonium acetate (channel А) acetonitrile (channel В) (Table 3) Table 3 А В column Flow rate (ml/min) Zorbax B mm Zorbax B mm 0.5 comment Irreversible sorbtion of analites Zorbax B mm Zorbax B mm Zorbax B mm 0.5 Partial separation Page 4 ARKAT UA, Inc
5 Arkivoc 2017, v, 1-32 Figure М solution of ammonium acetate doped with ammonium hydroxyde (channel А) - acetonitrile (channel В) (Table 4) Table 4 А В column Flow rate (ml/min) Zorbax B mm 0.5 comment Partial separation Figure 4. Page 5 ARKAT UA, Inc
6 Arkivoc 2017, v, М solution of ammonium acetate (channel А) acetonitrile (channel В) (Table 5) Table 5 А В column Flow rate (ml/min) Zorbax B mm Zorbax B mm Zorbax B mm 5 comment Total separation Figure 5. Analysis of mixture of TAs (Method 2) triturated with hydrochloric acid ample preparation To the 50 mg of TAs in the 6 ml vial was added 1 ml DMO and 20 µl conc. Hl. Vial was sonicated on ultrasonic bath for 5 minutes. To the solution was added 1 ml of DM and vial was shaked well. After separation of layers the lower layer was taken off and transferred to clear 1.5 ml vial. The choice of mobile phase For the optimal condition for HPL analysis was carried out separation of the TAs mixture in isocratic mode in the following systems of solvents: Page 6 ARKAT UA, Inc
7 Arkivoc 2017, v, 1-32 Deionized water (channel А) acetonitrile (channel В) (Table 6) Table 6 А В column Flow rate (ml/min) Zorbax B mm Zorbax B mm Zorbax B mm Zorbax B mm 0.5 comment Irreversible sorbtion of analites М solution of trisodium citrate 5.5-hydrate (channel A) acetonitrile (channel В) (Table 7) Table 7 А В column Flow rate (ml/min) Zorbax B mm Zorbax B mm :40 (3 min.) then gradient Zorbax B mm 0.5 to 50:50 60:40 (3 min.) then gradient Zorbax B mm 0.5 to 25:75 comment Irreversible sorbtion of analites After completion of all seven methods it was found that the most clear separation of TAs mixture was observed using the eluent system I with the phase relation А:В = 30:70. emi-preparative separation of TAs For the obtaining of TAs enriched fractions was carried out semi-preparative separation in manual mode on the semi-preparative column Zorbax B mm. Elution was accomplished in isocratic mode by using system consisting of 30% М solution of trisodium citrate 5.5-hydrate (channel A) 70% acetonitrile (channel В) (see. Fig. 6). Fractions which were obtained after separation were analyzed by direct input massspectrometry with EI ionization in negative mode. Page 7 ARKAT UA, Inc
8 Arkivoc 2017, v, 1-32 Figure 6. HPL-analysis for the reaction mixture obtained according to Method 2 (way ii). Peak number ompound number I 1 II 2 III 3 IV 4 V 5 ummary from HPL report are presented below: Page 8 ARKAT UA, Inc
9 Arkivoc 2017, v, 1-32 Mass-spectrometric investigation of fractions I-V was disturbed by high background signal from mobile phase due to peaks of clusters of trisodium citrate (see Fig. 7). But none of the fraction with TAs had targeted peaks overlapped with background peaks. Intens. [%] M, min #(1-8) m/z Figure Page 9 ARKAT UA, Inc
10 Arkivoc 2017, v, 1-32 Fraction I contained peak of ion [M-H] - = Da (Fig. 8): H 3 HO Molecular Weight = Exact Mass = Molecular Formula =30H36O36 Figure 8 Page 10 ARKAT UA, Inc
11 Arkivoc 2017, v, 1-32 Fraction II contained peak of ion [M-H] - = (Fig. 9): H 3 HO H 3 Molecular Weight = Exact Mass = Molecular Formula =20H24O26 Figure 9 Fraction III contained peak of ion [M-H] - = (Fig. 10): H 3 HO Molecular Weight = Exact Mass = Molecular Formula =30H36O37 Figure 10 Page 11 ARKAT UA, Inc
12 Arkivoc 2017, v, 1-32 Fraction IV contained peak of ion [M-H] - = (Fig. 11): H 3 HO Molecular Weight = Exact Mass = Molecular Formula =30H36O39 Figure 11 Fraction V contained peak of ion [M-H] - = (Fig. 12): Intens. [%] M, min #(1-8) HO [%] H48O44, M-nH, Molecular Weight = Exact Mass = Molecular Formula =40H48O m/z Figure 12 Page 12 ARKAT UA, Inc
13 Arkivoc 2017, v, 1-32 ummary table of results of investigation of fractions by direct input massspectrometry (Table 8): Table 8 Fraction Proposed molecular formula number I II 1 2 H 3 H 3 HO HO H 3 III IV 3 H 3 2 HO 4 H 3 HO Page 13 ARKAT UA, Inc
14 Arkivoc 2017, v, 1-32 V 5 HO Page 14 ARKAT UA, Inc
15 Arkivoc 2017, v, 1-32 Mass-spectrometric study of reaction mass from Method 2 by direct input The sample of solid sediment from Method 2 was dissolved in 100 µl of DMO and then it was diluted by 1 ml of acetonitrile. This solution was injected into mass-spectrometer by means of direct input. The results are presented on Fig and Table 9 below. Page 15 ARKAT UA, Inc
16 Arkivoc 2017, v, 1-32 Intens. [%] -M, min #(1-15) 10 H 12 O m/z Figure 13. urvey mass-spectra of reaction mass from Method 2, mass range Da. Page 16 ARKAT UA, Inc
17 Arkivoc 2017, v, 1-32 Intens. [%] -M, min #(1-15) H 12 O m/z Figure. 14 urvey mass-spectra of reaction mass from Method 2, mass range Da. Page 17 ARKAT UA, Inc
18 Arkivoc 2017, v, 1-32 Intens. [%] M, min #(1-15) m/z Figure 15 urvey mass-spectra of reaction mass from Method 2, mass range Da. Page 18 ARKAT UA, Inc
19 Arkivoc 2017, v, 1-32 Intens. [%] M, min #(1-15) m/z Figure 16 urvey mass-spectra of reaction mass from Method 2, mass range Da. Page 19 ARKAT UA, Inc
20 Arkivoc 2017, v, 1-32 Table 9 mass-list of mass-spectra of probe from Method 2 # m/z Res. /N I FWHM Page 20 ARKAT UA, Inc
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29 Arkivoc 2017, v, 1-32 Mass-spectrometric study of reaction mass from Method 3 by direct input The sample of solid sediment from Method 3 was dissolved in 100 µl of DMO and then it was diluted by 1 ml of acetonitrile. This solution was injected into mass-spectrometer by means of direct input. The results are presented on Fig. 17 and Table 10 below. Intens. [%] -M, min #(1-15) HO m/z Figure 17 Table 10 List of observed peaks in mass-spectra of sample from Method 3 # m/z Res. /N I FWHM Page 29 ARKAT UA, Inc
30 Arkivoc 2017, v, Page 30 ARKAT UA, Inc
31 Normalized Intensity 1.22 General Papers Arkivoc 2017, v, H NMR spectra of thiacalix[4]arene (5): 3126MR13_001001R.EP HO Acetone 0.2 HLOROFORM-d TM hemical hift (ppm) Page 31 ARKAT UA, Inc
32 Normalized Intensity General Papers Arkivoc 2017, v, NMR spectra of thiacalix[4]arene (5): 1206MR-13-_013001r HO 0.6 hloroform hemical hift (ppm) Page 32 ARKAT UA, Inc
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