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1 This journal is The Royal Society of Chemistry 0 Electronic Supplementary Information Zinc(II) ortho-hydroxyphenylhydrazo-β-diketonate Complexes and their Catalytic Ability towards Diastereoselective Nitroaldol (Henry) Reaction Maximilian N. opylovich, a Tatiana C. O. Mac Leod, a amran T. Mahmudov, a M. Fátima C. Guedes da Silva, a,b and Armando J. L. Pombeiro *a a Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, TU Lisbon, Av. Rovisco Pais, Lisbon, Portugal b Universidade Lusófona de Humanidades e Tecnologias, ULHT Lisbon, Av. Campo Grande nº 3, 49-04, Lisbon (Portugal) Corresponding author. addresses: pombeiro@ist.utl.pt (Armando J. L. Pombeiro).
2 This journal is The Royal Society of Chemistry 0 Analytical data for compounds 4. : Yield: % (based on pentane-,4-dione), black powder soluble in methanol, ethanol, acetone and insoluble in water and chloroform. Anal. Calcd for C H N O 3 (M = 0): C,.00; H, 5.45; N,.3. Found: C, 58.88; H, 5.4; N,.0. IR (Br, selected bands, cm ): 348 (NH), 309 (OH), 8 (C=O), 3 (C=O H), 599 (C=N). H NMR (300.3 MHz, DMSO-d ), δ:.4 (s, 3H, CH 3 ),.48 (s, 3H, CH 3 ),.9-. (4H, Ar H), 0.5 (s, H, OH), 4.58 (s, H, NH). 3 C{ H} NMR 5.48 MHz, DMSO-d ), δ:.5 (CH 3 ), 3. (CH 3 ), 4.9, 5.8, 0., and. (C Ar-H ), 9.3 (C Ar-NH-N ), 33. (C=N), 4.3 (C Ar-OH ), 9. and 9.4 (C=O). : Yield: 85.0 % (based on pentane-,4-dione), dark brown powder, soluble in ethanol, acetone and methanol and insoluble in water and chloroform. Anal. Calcd for C H N 3 O 5 (M=5.): C, 49.8; H, 4.8; N, Found: C, 49.85; H, 4.; N, IR (Br, selected bands, cm ): 34 (s, br) ν(oh), 3095 (s, br) ν(nh), 38 (s) ν(c=o), (s) ν(c=o H), 598 (s) ν(c=n) cm. H NMR (300.3 MHz, DMSO-d ): δ =.45 (s, 3H, CH 3 ),.49 (s, 3H, CH 3 ),.3.8 (m, 3H, Ar H),.55 (s, H, OH), 4. (s, H, NH). 3 C{ H} (5.48 MHz, DMSO-d ): δ =.55 (CH 3 ), 3.38 (CH 3 ), 0. (Ar H), 4.3 (Ar H),.30 (Ar H), (C=N), 3.0 (Ar NO ), 43.5 (Ar NH N), 45. (Ar OH), 9.5 (C=O), 9.44 (C=O) ppm. 3: Yield: 5 % (based on 5,5-dimethylcyclohexane-,3-dione), dark brown powder soluble in methanol, ethanol, acetone and insoluble in water and chloroform. Anal. Calcd for C 4 H N O 3 (M = ): C, 4.; H,.5; N, 0.8. Found: C, 4.09; H,.38; N,. IR (Br, selected bands, cm ): 3 (NH), 95 (OH), 50 (C=O), (C=O H), 594 (C=N). H NMR (300.3 MHz, DMSO-d ), δ:.0 (s, H, CH 3 ),.50 (s, H, CH ),.5 (s, H, CH ),.9-.4 (3H, Ar H), 0.5 (s, H, OH), 5.5 (s, H, NH). 3 C{ H} NMR 5.48 MHz, DMSO-d ), δ: 8.0 (CH 3 ), 30.4 (CH 3 ), 5.8 (CH ), 5.8 (CH ), 38.9 (C ipso ),.0, 0.3,.3 and 8.0 (C Ar-H ), 30.3 (C Ar-NH-N ), 3.0 (C=N), 4. (C Ar-OH ), 04. and 0.0 (C=O). 4: Yield: 83 % (based on 5,5-dimethylcyclohexane-,3-dione), dark brown powder soluble in methanol, ethanol, acetone and insoluble in water and chloroform. Anal. Calcd for C 4 H 5 N 3 O 5 (M = 305): C, 55.08; H, 4.9; N, 3.. Found: C, 55.00; H, 4.98; N, 3.8. IR (Br, selected bands, cm ): 3448 (NH), 300 (OH), 5 (C=O), 8 (C=O H), 59 (C=N). H NMR (0.3 MHz, DMSO-d ), δ: (s, H, CH 3 ),.50 (s, H, CH ),. (s, H, CH ),.-.4 (3H, Ar H), 0. (s, H, OH), 4.9 (s, H, NH). 3 C{ H} NMR (00. MHz, DMSO-d ), δ: 8.0 (CH 3 ), 30.3 (CH 3 ), 5.0 (CH ), 5.0 (CH ), 38. (C ipso ), 0., 4.5, and 5.3 (C Ar-H ), 3. (C Ar-NH-N ), 3. (C=N), 44.8 (C Ar-NO), 49.0 (C Ar-OH ), 03.4 and 0.3 (C=O).
3 This journal is The Royal Society of Chemistry 0 X-ray data of 5 8 Table S. Selected bond distances (Å) and angles ( ) for compounds Coordinated ligand C O (coordinated carbonyl).4(3).4().55(4).9(8) C O (free carbonyl).3(4).().4(4).(8) N N.83(3).8().(3).8() Coordination sphere of Zn Zn N.09().03(5).05().05(4) (axial sites).3(8) 3.5().(0).0(4) (equatorial sites) 03.8(9).5(9) Zn(μ-O) Zn core 04.3() 33.3() 0.4(9) 39.39(9) 04.(5) 3.(5) ZnOZn 98.(8) - 0.(9) - OZnO 8.84(8) -.8(9) - Longest Zn O.09() -.08() - Shortest Zn O.98() -.9() - Zn Zn () () - -membered metallacycle OZnN 8.38(9) 83.8(9) 8.05(9) 85.(4) Zn O.05().04(4).08().04(9) 5-membered metallacycle OZnN.03(9).4(8) 9.4(8) 8.9(5) Zn O ortho.09().03(4).08().999(0) 3
4 This journal is The Royal Society of Chemistry 0 Table S. Relevant hydrogen bonding distances (Å) and angles (º) [d(d A) / (D H A)] in 5 8. Compound D H A d(d A) (D H A) Symmetry codes 5 O4 H4 O i.9(4) 8(5) i: -x,-y,-z O0 H0A O i.54() 50 i: -x,-y,-z O0 H0B O4 ii.8(8) 0 ii: -x,-y,-z O0 H0A O3 i.9(3) (3) i: -x,-y,-z O0 H0C O3 ii.95(3) 5(3) ii: -+x,y,z 8 O0 H0B O3.0() 3 O0 H0A O3 i.0() 9 i: -x,/+y,/-z O HB O0 ii.() 3 ii: -x,/+y,/-z O HA O iii.5(5) 59 iii: -x,-y,-z O HB O0 iv.9(9) 43 iv: x,/-y,/+z Figure S. Fragments of the crystal packing diagram of 5 (top) and (down) showing the relative arrangement of four zinc dimers which are assembled into D chains (5) or D layers () via hydrogen bonds (dotted lines). The H atoms not involved in relevant interactions are omitted for clarity. 4
5 This journal is The Royal Society of Chemistry 0 Figure S. Structural representation of (top) and 8 (down) showing the intermolecular H-bonds (dotted lines), which generate D chains () or, also with the aid of crystallization water molecules (shown as red ball), a 3D network (8). The H atoms, apart from those involved in H-bonds, are omitted for clarity. Thermodynamics of interaction of zinc(ii) nitrate and ligand in solution ph-metric titration: The apparatus, general conditions, and methods of calculation are the same as those given in previous works. [,5]. The following mixtures (i) (iii) were prepared and titrated potentiometrically against standard 8 mol L NaOH in % (v/v) ethanol-water mixture at 98 : (i) 5.00 ml 0 M HCl ml.00 M Cl + 3 ml ethanol; (ii) 5.00 ml 0 M HCl ml M Cl ml ethanol ml 0 M ligand; (iii) 5.00 ml 0 M HCl ml M Cl ml ethanol ml 0 M ligand ml 0 M zinc salt. 5
6 This journal is The Royal Society of Chemistry 0 For each mixture, the volume was made up to 5 ml with bidistilled water before the titration process. These titrations were also repeated at temperatures of 308 and 38. Calculation of the stability constant (logk) of the Zn(II)-L complex formation by the Martell- Chaberek method: 8a To determine the stability constant, the following relationships were used: 8a ( a) c [H ] + [OH ] [L ] = +, [H ] + H L + + [H ] + + α = + [H ] + [H ], L( H ) k = c H L [L [L ] α ] α L(H) L(H) where c Zn =.00 0 M, c H L =.00 0 M, and and HL ( = / and = / ) and a is the neutralization point. Dissociation constants: a p =.35 = M and p = 0. =.03 0 M. Protonation constants: 0 = / = / =. 0 M and are the protonation constants of L = / = / =. 3 0 M. We titrated 5 ml of a solution with.00 0 M of H L and.00 0 M of Zn +, with a M solution of NaOH. i) After addition of 0.50 ml of M solution of NaOH to 5 ml of.00 0 M solution of Zn + +H L, we observed that ph 4.54 [H + ] = and [OH ] = M. Total concentration of NaOH: 0.50 ml M = 50.5 ml x M Total concentration of Zn + +H L: 5 ml.00 0 M = 50.5 ml x M x 0 4 =.9 M. x 0 4 x. 9 0 Neutralization point: a = = = 0. x α L( H ) k = [L ] = {( a) c H L =.98 M [H ] + [OH ]}/{[H ] + [H ] -3 0 {( - 0.4) } = (3.4 0 ) } = = = + [H ] [H ] = (3.4 0 ) = ( ) = logk = 9.8. M.
7 This journal is The Royal Society of Chemistry 0 (See Table S3). ii) After addition of.00 ml of M solution of NaOH to 5 ml of.00 0 M solution of Zn + +H L we observed that ph 4.3 [H + ] =.8 0 and [OH ] = M. Total concentration of NaOH:.00 ml M = 5.0 ml x M Total concentration of Zn + +H L: 5 ml.00 0 M = 5.0 ml x M x 0 =.5 M. x 0 x. 5 0 Neutralization point: a = = = 0. x. 9 0 α L( H ) k = = [L ] = {( a) c H L =.9 M [H ] + [OH ]}/{[H ] + [H ] -3 0 {( - 0.8) } = (.8 0 ) } = = [H ] + [H ] = (.8 0 ) = (9.9 0 ).3 0 (See Table S3). iii) etc. = logk = 9.8. M. 0 Table S3. Calculation of the stability constant of the zinc(ii) complex with L at 5 o C, in aqueous ethanol solution. V OH, ml a ph [H + ], M [OH ], M [L ], M α L( H ) logk logk = 9.8 ± 4 For determination of the thermodynamic functions of the complexation reaction, the following well known relationships were used: 8b G o ο =.303RTlogk; ΔH = {R(logk (T ) logk(t ) )}/{(/T3 ) (/T )}; S o = ( H o G o )/T. 3
8 This journal is The Royal Society of Chemistry 0 Table S4. Thermodynamic characteristics of the formation of the complex of Zn(II) with L in aqueous ethanol solution. T, logk G o, kj mol H o, kj mol S o, J mol 98± ±4.± ±.8 308± ± 3.8±.8 38± ± Thermal decomposition of 8 00 TG Deriv. Weight (mg/min) 00 TG Deriv. Weight (mg/min) 00 0 TG Derivative Weight (mg/min) 00 TG Derivative Weight (mg/min) 00 0 TG Derivative Weight (mg/min) 00 TG Derivative Weight (mg/min) 8
9 This journal is The Royal Society of Chemistry TG Derivative Weight (mg/min) 00 TG Figure S3. TG and curves of Derivative Weight (mg/min) Table S5. Thermal behaviour of 8. Compound Temperature range, o C Weight loss, % peak temperature ( o C)
10 This journal is The Royal Society of Chemistry 0 Catalytic studies 00 Yield (%) 0 0 complex ligand Time (h) Figure S4. Accumulation of β-nitroalkanol (along the initial 48 h) in the Henry reaction of benzaldehyde and nitroethane, catalyzed by complex ( ) and ligand ( ). Table S. Variation of benzaldehyde concentration with time Time, h [benzaldehyde], mol L ln[benzaldehyde], mol L ln[benzaldehyde], mol L y = -454x 0.54 R = Time, h Figure S5. Plot of ln[benzaldehyde] vs. time. 0
11 This journal is The Royal Society of Chemistry 0 A benzaldehyde + nitroethane 5 + benzaldehyde nitroethane λ, nm Figure S. UV-vis spectra of starting materials and products for the Henry reaction: benzaldehyde (), nitroethane (), benzaldehyde + nitroethane (3), (4), benzaldehyde + nitroethane + (5), 5 (), benzaldehyde + nitroethane + 5 (); [benzaldehyde] = [nitroethane] = M, [5] = [] =.00 0 M in methanol. A h h 30 min 0 min λ, nm Figure S. UV-vis monitoring of Henry reaction: [benzaldehyde] = [nitroethane] = M; [] =.00 0 M in methanol.
12 This journal is The Royal Society of Chemistry 0 Calculation of the yield and selectivity for complex in the Henry reaction Total amount of compounds (see Fig. S): Bezaldehyde + erythro + threo = = 9. Percentage of the unreacted bezaldehyde: % x =.4 % x Conversion of benzaldehyde = yield of β-nitroalkanols = 00.4 = 9. %. Yield of erythro: % x x = 3. % Yield of threo: % x x = 4.5 %. See Table, Entry 9. Selectivity: Sum of erythro + threo = = 9.. Selectivity of erythro: % x x = 4 %. Selectivity of threo: % x x = %.
13 This journal is The Royal Society of Chemistry 0 Figure S8. Example of integration in the H NMR spectrum for the determination of Henry reaction products (Table, Entry 9). Table S. Compositon of some catalysts from Table Reference f Lanthanum (La(O i Pr) 3 )/sodium source/amide ligand heterobimetallic catalyst f Neodymium (Nd(O i Pr) 3 )/sodium source/amide ligand heterobimetallic catalyst g Rh complex in the presence of a silyl ketene acetal 3
14 This journal is The Royal Society of Chemistry 0 n Chiral binuclear Cu(II) Schiff base complexes o,,3,3-tetramethyl guanidine (TMG)-based ionic liquid m Zn Brucine-derived aminoalcohol p Ferrocenyl-substituted aziridinylmethanol (Fam) as a catalyst with Zn c Phenoxide substituted Cu complex r Mono ethylenediamine Zn complex 4
15 This journal is The Royal Society of Chemistry 0 s Zn(II) complexes with chiral guanidine ligands RHN t N NH O HN O HN O NHR R= O CH 3CH3 C C O CH 3 RHN NHR 3 Tertiary amines dendritically encapsulated within a flexible peptidic shell 5
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