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1 Supporting Information Structural NMR and ab initio Study of Salicylhydroxamic and p- ydroxybenzohydroxamic acids: Evidence for an Extended Aggregation Begoña García,,* Fernando Secco,, * Saturnino Ibeas, Asunción Muñoz, Francisco. J. oyuelos, José M. Leal, María L. Senent and Marcella Venturini. Universidad de Burgos, Departamento de Qumica, Burgos, Spain Università di Pisa, Dipartimento di himica e himica Industriale, Pisa, Italy onsejo Superior de investigaciones ientificas, Departamento de Astrofisica Molecular e Infrarroja, Instituto de Estructura de la Materia, Madrid, Spain. begar@ubu.es ontent page omputational Data Acid Dissociation Equilibria S2-S45 S46 1 NMR Solution Study S47-S48 Derivation of Equation (5) S49 - S1 -
2 - S2 - N N N N N N N N N B-Z-Amide N N N A-E- Imide B-Z- Imide A-E-4 A-E-1 A-E-5 B-Z-1 B-Z-2 B-Z-3 B-Z-4 B-Z-1 B-Z-5 B-Z-6 B-Z-7
3 - S3 - N N N N B-E-Amide N N N B-E- Imide B-E-1 B-E-2 B-E-3 B-E-4 B-E-1 B-E-5 Scheme S1. Stable geometry for neutral and anionic A-SA and B-SA forms
4 Table S1. Relative Energy (kcal/mol) and Dipole Moment (Debyes) of the Neutral Forms and Anions of SA with the B3LYP/AUG-cc-pVDZ A-Salicylhydroxamic acid Neutral Forms E R µ Z-amide a Z-imide E-amide E-imide Anions Z-1 b Z Z Z Z E E E E E B-Salicylhydroxamic acid Neutral Forms E R µ Z-amide a Z-imide E-amide E-imide Anions Z-1 b Z Z Z Z E E E Z-6 c Z A-SA a) E a = a.u; b) E b = a.u; B-SA a) E a = a.u; b) E b = a.u; c) Ec= a.u. - S4 -
5 Table S2. Dissociation Energies (kcal/mol) of SA A-Salicylhydroxamic acid RF/cc-pVDZ Z-amide Z E-amide E Z-amide Z E-amide E Z-imide Z E-imide E B3LYP/AUG-cc-pVDZ Z-amide Z E-amide E Z-amide Z E-amide E Z-amide Z E-amide E E-imide E Z-imide Z E-imide E B-Salicylhydroxamic acid RF/cc-pVDZ Z-amide Z E-amide E Z-amide Z Z-amide Z E-amide E Z-imide Z Z-imide Z E-imide E Z-3 Z Z-3 Z B3LYP/cc-pVDZ Z-amide Z E-amide E Z-amide Z Z-amide Z E-amide E Z-imide Z Z-imide Z E-imide E Z-3 Z Z-3 Z S5 -
6 Table S6. A-Z-Amide (RF/cc-pVDZ ) N SF Done: E(RF) = A.U. after 9 cycles N SF Done: E(RF) = A.U. after 13 cycles S6 -
7 N SF Done: E(RF) = A.U. after 10 cycles Table S7. A-Z-Imide (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 8 cycles S7 -
8 SF Done: E(RF) = A.U. after 9 cycles X= Y= Z= Tot= SF Done: E(RF) = A.U. after 9 cycles X= Y= Z= Tot= Table S8. A-E-Amide (RF/cc-pVDZ ) N S8 -
9 SF Done: E(RF) = A.U. after 10 cycles N SF Done: E(RF) = A.U. after 10 cycles SF Done: E(RF) = A.U. after 12 cycles - S9 -
10 Table S9. A-Z-1 (RF/cc-pVDZ ) N SF Done: E(RF) = A.U. after 10 cycles X= Y= Z= Tot= Table S10. A-Z-2 (RF/cc-pVDZ ) N SF Done: E(RF) = A.U. after 10 cycles X= Y= Z= Tot= S10 -
11 Table S11. A-Z-3 (RF/cc-pVDZ ) N SF Done: E(RF) = A.U. after 10 cycles X= Y= Z= Tot= Table S12. A-Z-4 (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 9 cycles X= Y= Z= Tot= S11 -
12 Table S13. A-Z-5 (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 10 cycles Dipole moment (Debye): X= Y= Z= Tot= Table S14. A-E-1 (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 12 cycles X= Y= Z= Tot= S12 -
13 Table S15. A-E-2 (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 10 cycles X= Y= Z= Tot= Table S16. A-E-3 (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 10 cycles X= Y= Z= Tot= S13 -
14 Table S17. A-E-4 (RF/cc-pVDZ ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z SF Done: E(RF) = A.U. after 10 cycles X= Y= Z= Tot= Table S18. A-E-5 (RF/cc-pVDZ ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J N X S14 -
15 SF Done: E(RF) = A.U. after 7 cycles X= Y= Z= Tot= Table S19. A-E-6 (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 9 cycles X= Y= Z= Tot= Table S20. A-E-7 (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 11 cycles X= Y= Z= Tot= S15 -
16 Table S21. A-Z-Amide (RF/cc-pVDZ ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J N SF Done: E(RF) = A.U. after 13 cycles Dipole moment (Debye): X= Y= Z= Tot= Table S22. A-Z-Imide (E r = 7.7 kcal/mol) (RF/cc-pVDZ ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J N S16 -
17 SF Done: E(RF) = A.U. after 12 cycles X= Y= Z= Tot= Table S23. A-E-Amide (E r = 2.5kcal/mol) (RF/cc-pVDZ ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J N SF Done: E(RF) = A.U. after 10 cycles Dipole moment (Debye): X= Y= Z= Tot= S17 -
18 Table S24. A-E-Imide (14.92 kcal/mol) (RF/cc-pVDZ ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J N SF Done: E(RF) = A.U. after 9 cycles Dipole moment (Debye): X= Y= Z= Tot= Table S25. B-Z-Amide (RF/cc-pVDZ ) N SF Done: E(RF) = A.U. after 10 cycles - S18 -
19 N E(RF) = A.U. after 13 cycles Table S26. B-Z-Imide (RF/cc-pVDZ ) ( 1) ( 2) ( 18) ( 3) ( 19) ( 34) ( 4) ( 20) ( 35) ( 5) ( 21) ( 36) ( 6) ( 22) ( 37) ( 7) ( 23) ( 38) N ( 8) ( 24) ( 39) ( 9) ( 25) ( 40) ( 10) ( 26) ( 41) ( 11) ( 27) ( 42) ( 12) ( 28) ( 43) ( 13) ( 29) ( 44) ( 14) ( 30) ( 45) ( 15) ( 31) ( 46) ( 16) ( 32) ( 47) ( 17) ( 33) ( 48) 0 SF Done: E(RF) = A.U. after 9 cycles ( 1) ( 2) ( 18) ( 3) ( 19) ( 34) 0 - S19 -
20 ( 4) ( 20) ( 35) ( 5) ( 21) ( 36) ( 6) ( 22) ( 37) ( 7) ( 23) ( 38) N ( 8) ( 24) ( 39) ( 9) ( 25) ( 40) ( 10) ( 26) ( 41) ( 11) ( 27) ( 42) ( 12) ( 28) ( 43) ( 13) ( 29) ( 44) ( 14) ( 30) ( 45) ( 15) ( 31) ( 46) ( 16) ( 32) ( 47) ( 17) ( 33) ( 48) 0 SF Done: E(RF) = A.U. after 9 cycles ( 1) ( 2) ( 18) ( 3) ( 19) ( 34) ( 4) ( 20) ( 35) ( 5) ( 21) ( 36) ( 6) ( 22) ( 37) ( 7) ( 23) ( 38) N ( 8) ( 24) ( 39) ( 9) ( 25) ( 40) ( 10) ( 26) ( 41) ( 11) ( 27) ( 42) ( 12) ( 28) ( 43) ( 13) ( 29) ( 44) ( 14) ( 30) ( 45) ( 15) ( 31) ( 46) ( 16) ( 32) ( 47) ( 17) ( 33) ( 48) 0 SF Done: E(RF) = A.U. after 9 cycles Table S27. B-E-Amide (RF/cc-pVDZ ) N S20 -
21 SF Done: E(RF) = N A.U. after 12 cycles SF Done: E(RF) = A.U. after 15 cycles - S21 -
22 Table S28. B-Z-1 (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 11 cycles X= Y= Z= Tot= Table S29. B-Z-2 (E=33.3) (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 9 cycles X= Y= Z= Tot= S22 -
23 Table S30. B-Z-3 (E r =3.8) (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 9 cycles X= Y= Z= Tot= Table S31. B-Z-4 (E r =21.8) (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 11 cycles X= Y= Z= Tot= S23 -
24 Table S32. B-Z-5 (RF/cc-pVDZ ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J N X SF Done: E(RF) = A.U. after 7 cycles X= Y= Z= Tot= Table S33. B-E-1 (RF/cc-pVDZ ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J N X S24 -
25 SF Done: E(RF) = A.U. after 6 cycles X= Y= Z= Tot= Table S34. B-E-2 (RF/cc-pVDZ ) converge to B-E-3 Table S35. B-E-3 (RF/cc-pVDZ ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J N X SF Done: E(RF) = A.U. after 14 cycles X= Y= Z= Tot= Table S36. B-E-4 (RF/cc-pVDZ ) converge to B-E-5 - S25 -
26 Table S37. B-E-5 (RF/cc-pVDZ ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J SF Done: E(RF) = A.U. after 8 cycles X= Y= Z= Tot= Table S38. B-E-6 (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 14 cycles X= Y= Z= Tot= S26 -
27 Table S39. B-E-7 (E r =2.2kcal/mol) (RF/cc-pVDZ ) SF Done: E(RF) = A.U. after 10 cycles X= Y= Z= Tot= Table S40. A-Z-Amide (Rb3lyp/aug-cc-pVDZ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J SF Done: E(RB+F-LYP) = A.U. after 9 cycles X= Y= Z= Tot= S27 -
28 Table S41. A-Z-Imide (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z SF Done: E(RB+F-LYP) = A.U. after 9 cycles X= Y= Z= Tot= Table S42. A-E-Amide (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z S28 -
29 SF Done: E(RB+F-LYP) = A.U. after 10 cycles X= Y= Z= Tot= Table S43. A-E-Imide (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z SF Done: E(RB+F-LYP) = A.U. after 10 cycles X= Y= Z= Tot= Table S44. A-Z-1 (Rb3lyp/aug-cc-pVDZ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J S29 -
30 SF Done: E(RB+F-LYP) = A.U. after 14 cycles X= Y= Z= Tot= Table S45. A-Z-2 (Rb3lyp/aug-cc-pVDZ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J SF Done: E(RB+F-LYP) = A.U. after 23 cycles Dipole moment (Debye): X= Y= Z= Tot= S30 -
31 Table S46. A-Z-3 (Rb3lyp/aug-cc-pVDZ) Z-MATRIX (ANGSTRMS AND DEGREES) D ent Atom N1 Length/X N2 Alpha/Y N3 Beta/Z J SF Done: E(RB+F-LYP) = A.U. after 14 cycles X= Y= Z= Tot= Table S47. A-Z-4 (Rb3lyp/aug-cc-pVDZ) converge to A-Z-1 Table S48. A-Z-5 (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z S31 -
32 SF Done: E(RB+F-LYP) = A.U. after 10 cycles X= Y= Z= Tot= Table S49. A-E-1 (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z SF Done: E(RB+F-LYP) = A.U. after 10 cycles X= Y= Z= Tot= Table S50. A-E-2 (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z S32 -
33 SF Done: E(RB+F-LYP) = A.U. after 11 cycles X= Y= Z= Tot= Table S51. A-E-3 (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z SF Done: E(RB+F-LYP) = A.U. after 10 cycles X= Y= Z= Tot= S33 -
34 Table S52. A-E-4 (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z SF Done: E(RB+F-LYP) = A.U. after 11 cycles X= Y= Z= Tot= Table S53. A-E-5 (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z S34 -
35 SF Done: E(RB+F-LYP) = A.U. after 9 cycles X= Y= Z= Tot= Table S54. A-E-6 (Rb3lyp/aug-cc-pVDZ) SF Done: E(RB+F-LYP) = A.U. after 13 cycles X= Y= Z= Tot= Table S55. A-E-7 (Rb3lyp/aug-cc-pVDZ) SF Done: E(RB+F-LYP) = A.U. after 17 cycles X= Y= Z= Tot= S35 -
36 Table S56. B-Z-Amide (RF/cc-pVDZ) N SF Done: E(RF) = A.U. after 10 cycles X= Y= Z= Tot= Table S57. B-Z-Imide (E r =0.1 kcal/mol) (RF/cc-pVDZ) SF Done: E(RF) = A.U. after 8 cycles X= Y= Z= Tot= S36 -
37 Table S58. B-E-Amide (E r =6.9 Kcal/mol) (RF/cc-pVDZ) N SF Done: E(RF) = A.U. after 13 cycles X= Y= Z= Tot= Table S59. B-E-Imide (E r =8.5 Kcal/mol) (RF/cc-pVDZ) SF Done: E(RF) = A.U. after 12 cycles X= Y= Z= Tot= S37 -
38 Table S60. B-Z-Amide (Rb3lyp/aug-cc-pVDZ) enter Atomic Atomic oordinates (Angstroms) Number Number Type X Y Z SF Done: E(RB+F-LYP) = A.U. after 10 cycles X= Y= Z= Tot= Table S61. B-Z-Imide (Rb3lyp/aug-cc-pVDZ) S38 -
39 SF Done: E(RB+F-LYP) = A.U. after 13 cycles X= Y= Z= Tot= Table S62. B-E-Amide (Rb3lyp/aug-cc-pVDZ) SF Done: E(RB+F-LYP) = A.U. after 9 cycles X= Y= Z= Tot= Table S63. B-E-Imide (Rb3lyp/aug-cc-pVDZ) S39 -
40 SF Done: E(RB+F-LYP) = A.U. after 11 cycles X= Y= Z= Tot= Table S64. B-Z-1 (Rb3lyp/aug-cc-pVDZ) SF Done: E(RB+F-LYP) = A.U. after 12 cycles X= Y= Z= Tot= Table S65. B-Z-2 (Rb3lyp/aug-cc-pVDZ) SF Done: E(RB+F-LYP) = A.U. after 12 cycles X= Y= Z= Tot= S40 -
41 Table S66. B-Z-3 (Rb3lyp/aug-cc-pVDZ) SF Done: E(RB+F-LYP) = A.U. after 11 cycles X= Y= Z= Tot= Table S67. B-Z-4 (Rb3lyp/aug-cc-pVDZ) SF Done: E(RB+F-LYP) = A.U. after 17 cycles X= Y= Z= Tot= S41 -
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