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1 Supplementary Information Conformational Analysis, Experimental and GIA-DFT C NMR Chemical Shift Calculation on 2 -Hydroxy-,4,-trimethoxy-chalcone Fabio Luiz P. Costa, a Paulo F. Gomes, b Andressa K. Silva c and Luciano M. Lião*,c a Departamento de Química and b Departamento de Física, Universidade Federal de Goiás, BR 64, km 92, 800, Jataí-G, Brazil c Instituto de Química, Universidade Federal de Goiás, Av. Esperança s/n, Campus Samambaia, Goiânia-G, Brazil ' H ppm Figure S. C NMR spectrum (2.7 MHz, CDCl ) of 2 -hydroxy-,4,-trimethoxy-chalcone. * fabbioquimica@gmail.com; lucianoliao@ufg.br

2 ppm 0 60 ' 70 H ppm Figure S2. HSQC NMR contour map (00 MHz, CDCl ) of 2 -hydroxy-,4,-trimethoxy-chalcone. ppm 20 ' 40 H ppm Figure S. HMBC NMR contour map (00 MHz, CDCl ) of 2 -hydroxy-,4,-trimethoxy-chalcone.

3 H ' A H H 2 N ' B Me Figure S4. Structure of (E)--(4-hydroxy--methoxyphenyl)--(,-di-tert-butyl-4-hydroxyphenyl)prop-2-en- -one (A) and (E)--(4-aminophenyl)--(,4-dimethoxyphenyl)prop-2-en--one (B). Figure S. Superposition of the four lowest energy conformations of (E)--(4-hydroxy--methoxyphenyl)- -(,-di-tert-butyl-4-hydroxyphenyl)prop-2-en--one molecule.

4 Figure S6. DFT-optimized structures of the four more stable conformers,, 2, and 4, respectively, of (E)--(4-hydroxy--methoxyphenyl)--(,-di-tert-butyl-4-hydroxyphenyl)prop-2-en--one. For relative energies and abundances of the conformers, see Table S. Figure S7. Superposition of the five lowest energy conformations of (E)--(4-aminophenyl)- -(,4-dimethoxyphenyl)prop-2-en--one molecule.

5 Figure S8. DFT-optimized structures of the five more stable conformers,, 2,, 4 and, respectively, of (E)--(4-aminophenyl)--(,4-dimethoxyphenyl)prop-2-en--one. For relative energies and abundances of the conformers, see Table S.

6 Table S. DFT, thermo chemical parameter and DFT population for the 7 more significant conformations of (E)--(4-hydroxy--methoxyphenyl)--(,-di-tert-butyl-4-hydroxyphenyl)prop-2-en--one Conformer ΔE a / Bolt. ΔE c / Bolt. ΔE e / Bolt. ΔG g / Bolt. (kcal mol - ) dist. b / % (kcal mol - ) dist. d / % (kcal mol - ) dist. f / % (kcal mol - ) dist. h / % a Relative MMFF energy of conformers obtained from Monte Carlo analysis; b MMFF Boltzmann population of the conformers; c relative BLYP/6-G(d) single point energy of conformers obtained from Monte Carlo analysis; d BLYP/6-(g) single point energy Boltzmann population of the conformers; e relative mpwpw9/ 6-G(d) energy minimization of the conformers; f mpwpw9/6-g(d) energy minimization Boltzmann population of the conformers; g relative mpwpw9/6-g(d) sum of electronic and free energy of the conformers; h mpwpw9/6-g(d) Boltzmann population calculated from ΔG values of the conformers.

7 Table S2. Calculated (scaled) and differences between experimental C NMR chemical shifts (in ppm) in the (E)--(4-hydroxy--methoxyphenyl)--(,-di-tert-butyl-4-hydroxyphenyl)prop-2-en--one relative to TMS, for approaches (I) and (II) Nuclei δ exp Approach (I) Approach (II) δ a calc (δ scal ) b δ calc (δ scal ) δ a calc (δ scal ) b δ calc (δ scal ) C (26.) 4.79 (0.07) 20.8 (2.6).7 ( 0.7) *C (2.).2 (-0.4) 20. (2.).0 ( 0.7) *C 6.. (6.9) 4.97 (0.8) 0.9 (6.2).62 ( 0.29) C (7.).28 (.06) 0.7 (7.0).74 (0.7) *C 6.. (6.9).2 (0.8) 0.9 (6.2).62 ( 0.29) *C (2.).26 ( 0.4) 20. (2.).0 ( 0.7) **C (6.8).8 (2.44) 4. (.0) 0.09 (0.9) **C (.7).4 (.49) 29. (29.8) 0.68 ( 0.4) α (.) 8.06 (.74) 09.9 (7.) 8.9 (.67) β (48.).8 (2.) 4. (47.4) 4.06 (.79) β (8.4).8 (.6) 7.6 (8.2).8 (.82) C. 2.7 (0.8).80 ( 0.7) 24.9 (0.0) 6.6 (.) C (2.8) 4.48 (0.2) 8.0 (22.7).47 ( 0.79) C (.2) 4.68 ( 0.4) 08.0 (2.2).72 (.4) C (0.) 6.00 ( 0.0) 4.6 (49.) 6.4 ( 0.8) C (44.6) 8.02 ( 2.29) 8. (44.0) 8.6 ( 2.86) C (2.) 2.47 (.72) 07. (.).29 (0.86) (6.2).4 (0.06). (4.).00 (.6) a Calculated chemical shifts (δ calc = σ TMS σ aver or σ lowe ) obtained by TMS subtraction; b scaled chemical shifts (δ scal =.0δ calc.22) obtained by the generated universal scaling factor. *The δ calc and δ scal for C2 and C6, C and C were arithmetically averaged; **the δ calc and δ scal for C7 and C8, were arithmetically averaged from the two t-butyl carbons and of the methyl carbons of the two t-butyl ligands, respectively.

8 Table S. DFT, thermo chemical parameter and DFT population for the more significant conformations of (E)--(4-aminophenyl)--(,4-dimethoxyphenyl)prop-2-en--one Conformer ΔE a / Bolt. ΔE c / Bolt. ΔE e / Bolt. ΔG g / Bolt. (kcal mol - ) dist. b / % (kcal mol - ) dist. d / % (kcal mol - ) dist. f / % (kcal mol - ) dist. h / % a Relative MMFF energy of conformers obtained from Monte Carlo analysis; b MMFF Boltzmann population of the conformers; c relative BLYP/6-G(d) single point energy of conformers obtained from Monte Carlo analysis; d BLYP/6-(g) single point energy Boltzmann population of the conformers; e relative mpwpw9/ 6-G(d) energy minimization of the conformers; f mpwpw9/6-g(d) energy minimization Boltzmann population of the conformers; g relative mpwpw9/6-g(d) sum of electronic and free energy of the conformers; h mpwpw9/6-g(d) Boltzmann population calculated from ΔG values of the conformers.

9 Table S4. Calculated (scaled) and differences between experimental ¹³C NMR chemical shifts (in ppm) in the (E)--(4-aminophenyl)--(,4-dimethoxyphenyl)prop-2-en--one relative to TMS, for approaches (I) and (II) Nuclei δ exp Approach (I) Approach (II) δ a calc (δ scal ) b δ calc (δ scal ) δ a calc (δ scal ) b δ calc (δ scal ) C (28.8) 4.9 (0.7) (26.9).9 (.06) C (22.40).9 (.08).09 (7.) 8.2 (.79) C (.7).68 (.) 0.67 (09.7) 7.4 (.7) C (0.78) 6.8 ( 0.6) 4.88 (49.8) 7.46 (.49) C (49.0) 6.9 ( 0.26) 4.94 (47.8) 7. (.48) C (8.99) 0.04 (4.46). (.86).02 (.) Cα (7.) 9.74 (.0).6 (.70).49 ( 7.) Cβ (46.84) 4.29 (.4) (46.07).02 (0.77) C (8.44).0 (.) 7.4 (82.96).6 ( 6.0) C (29.77). (.) 2.6 (28.2) 8.9 (.2) *C (.69) 7 (.98) 26.8(.69) (0.) *C (.09) (0.) 07.0 (.44) 7.06 ( 2.92) C (48.) 2. ( 6.64) 4.68 (47.). ( 7.64) *C (.09).0 (.27) 07.0 (.44) 7.06 ( 2.92) *C (.69) (0.) 26.8 (.69) (0.) (7.4) 0. (.42) 2.7 (4.7).26 (.84) (7.4) 0. (.42) 2.7 (4.7).26 (.84) a Calculated chemical shifts (δ calc = σ TMS σ aver or σ lowe ) obtained by TMS subtraction; b scaled chemical shifts (δ scal =.0δ calc.22) obtained by the generated universal scaling factor. *The δ calc and δ scal for C2 and C6, C and C were arithmetically averaged. Reference. Costa, F. L. P.; de Albuquerque, A. C. F.; Borges, R. M.; dos Santos Jr., F. M.; de Amorim, M. B.; J. Comput. Theor. Nanosci. 204,, 29.

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