Computational details, X-ray datas and spectral copies of 1 H, 13 C NMR of compounds obtained in this study

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1 Stereo, Regio-, and Chemoselective [3+2]-Cycloaddition of (2E,4E)-Ethyl 5-(Phenylsulfonyl)penta-2,4-dienoate with Various Azomethine Ylides, Nitrones, and Nitrile Oxides: Synthesis of Pyrrolidine, Isoxazolidine, and Isoxazoline Derivatives and a Computational Study Ulaganathan Sankar a, Ch. Venkata Surya Kumar b, V. Subramanian b *, K. K. Balasubramanian c * and S. Mahalakshimi a a Department of Chemistry, Pachaiyappa s College, University of Madras, Chennai , India. b Chemical Laboratory, CSIR-Central Leather Research Institute, Adyar, Chennai , India. c INSA Senior Scientist, Department of Chemistry, Indian Institute of Technology Madras, Chennai , India. kkbalu@hotmail.com, subuchem@hotmail.com Computational details, X-ray datas and spectral copies of 1 H, 13 C NMR of compounds obtained in this study Table of Contents 1. Computational Data..S2-S30 2. X-ray data of 4a and 9a...S31-S34 3. Spectral Data....S35-S86 S1

2 1. Computational Data Test calculations have been performed on Scheme 1 with dispersion corrected wb97xd/6-31g(d) method to verify the results. The solvent (1,4-dioxane) effect has also been included with PCM model. The results are similar to the B3LYP/6-31G(d) method. The activation energy difference ranges from kcal/mol. However, there is no significant change in the trend in the energies. (a) B3LYP/6-31G(d) in gas phase (b) wb97xd/6-31g(d) with solvent (1,4-Dioxane) Figure S1 Energy profiles for scheme 1 with (a) B3LYP/6-31G(d) method and (b) wb97xd/6-31g(d) method with solvent effects. (a) (b) Figure S2 Energy profile for (1,3) dipolar cycloaddition of (a) s-cis diene and (b) s-trans diene with 3a (Scheme 1). S2

3 Figure S3 Optimized geometries of TSs for exo and endo conformations of (Scheme 2). Figure S4 Energy profile for the formation of exo and endo confirmations of Scheme 2 (1 + 8a). Figure S5 Optimized geometries of TSs for exo and endo conformations of the reaction of 1 with ylide of 11a (Scheme 3), computed using B3LYP/6-31g(d) level. S3

4 Figure S6 Energy profile diagram for exo and endo conformations of the reaction of 1 with ylide of 11a (Scheme 3). Figure S7 Optimized geometries of TSs for exo and endo conformations of the reaction of 1 with ylide of 2a (Scheme 4). S4

5 Figure S8 Energy profile diagram of the reaction of 1 with ylide of 2a (Scheme 4). Figure S9 Optimized geometries of TSs for exo and endo conformations of the reaction of 1 with ylide of 20b (Scheme 6). S5

6 Figure S10 Energy profile diagram of exo-endo confirmations for the reaction of 1 with dipole of 20b (Scheme 6). Figure S11 Optimized geometries of TSs for exo and endo conformations of the reaction of 1 with ylide of 22b (Scheme 6). S6

7 Figure S12 Energy profile diagram of exo-endo confirmations for the reaction of 1 with dipole of 22b (Scheme 6). Table S1 HOMO, LUMO energies (in a.u.) and electronic chemical potential (μ, in a.u.), chemical hardness (η, in a.u.), global electrophilicity (ω, in ev), global softness (s, in a.u.) and global nucleophilicity (N, in ev) of diene 1 and all the ylides with different substitutions. Reactant HOMO LUMO μ=(el+eh)/2 η=el-eh ω s N a Dipoles of 3 3a b c d e Dipoles of 8 8a b c d e Dipoles of 11 11a b S7

8 11c d e Dipoles of 2a 2a Dipoles of 16 16a b c d Dipoles of 18 18a b c d Dipoles of 20 20a b Dipoles of 22 22a b Table S2 Local reactive indices of reactants calculated using B3LYP/dnd method, local electrophilicity (ω k in ev) and local nucleophilicity in (N k, in ev). Reactant Atom F + F - F 0 ω k N N k 1 C C C C Dipoles of 3 3a C C b C C c C C d C C Dipoles of 8 8a C C b C C c C S8

9 C d C C Dipoles of 11 11a C C b C C c C C d C C Dipoles of 2a 2a C C Dipoles of 16 16a C C b C C c C C d C C Dipoles of 18 18a C C b C C c C C d C C Dipoles of 20 C a O C b O Dipoles of 22 C a O C b O Table S3 Imaginary frequencies (cm -1 ) and lengths of bond forming C-C bonds (in Å) of the TSs. TS Frequency Bond length (TSs) d TS/P Scheme:1 3aTS i C1-C C2-C aTS i C2-C C1-C S9

10 3aTS i 3aTS i 8aTS i 8aTS i 8aTS i 8aTS i 11aTS i 11aTS i 11aTS i C3-C C4-C C4-C C3-C Scheme:2 C1-C C2-C C2-C C1-C C3-C C4-C C4-C C3-C Scheme:3 C1-C C2-C C2-C C1-C C3-C C4-C aTS i C4-C C3-C Scheme:4 2aTS i C1-C C2-C aTS i C4-C C3-C Scheme:5(16) 16aTS i C1-C C2-C aTS i C2-C C1-C aTS i C4-C C3-C aTS i C3-C C4-C Scheme:5(18) 18aTS i C1-C C2-C aTS i C2-C C1-C aTS i C4-C C3-C aTS i C3-C C4-C Scheme:6 20bTS i C4-O C3-C bTS i C3-O S10

11 20bTS i 20bTS i 22bTS i 22bTS i 22bTS i 22bTS i C4-C C1-O C2-C C2-O C1-C C4-O C3-C C3-O C4-C C1-O C2-C C2-O C1-C Table S4 Distortion, interaction and activation energies of 1,3-dipolar cycloaddition reactions. TS E dist (kcal/mol) Diene Dipole Total E int(kcal/mol) E (kcal/mol) Scheme 1 TS TS TS TS Scheme 2 TS TS TS TS Scheme 3 TS TS TS TS Scheme 4 TS TS Scheme 5 (16) TS TS TS TS Scheme 5 (18) TS TS TS TS Scheme 6 (20b) TS TS TS TS Scheme 6 (22b) TS TS TS S11

12 TS Scheme 7 (Bis addition) 25C_TS C _TS Table S5 Distortion, interaction and activation energies of exo-endo isomers TS E dist (kcal/mol) Diene Dipole Total E int(kcal/mol) E (kcal/mol) Scheme 1 TS1ex TS1en Scheme 2 TS1ex TS1en Scheme 3 TS1ex TS1en Scheme 4 TS2ex TS2en Scheme 6 (20b) TS2ex TS2en Scheme 6 (22b) TS4ex TS4en Table S6 Activation of Gibbs Free Energies (in kcal/mol), Enthalpies (in kcal/mol) and energies (in kcal/mol) of stationary points computed at gas phase using B3LYP/6-31g (d). Reactants G G H H E E Scheme:1 3aTS aTS aTS aTS Scheme:2 8aTS aTS aTS aTS Scheme:3 11aTS S12

13 11aTS aTS aTS Scheme:4 2aTS aTS Scheme:5(16) 16aTS aTS aTS aTS Scheme:5(18) 18aTS aTS aTS aTS Scheme:6 20bTS bTS bTS bTS bTS bTS bTS bTS Table S7 Activation of Gibbs Free Energies (in kcal/mol), Enthalpies (in kcal/mol) and energies (in kcal/mol) of stationary points of Exo and Endo isomers computed at gas phase using B3LYP/6-31g (d). TS G G H H E E Scheme:1 3aTS1ex S13

14 3aTS1en Scheme:2 8aTS1ex aTS1en Scheme:3 11aTS1ex aTS1en Scheme:4 2aTS2ex aTS2en Scheme:6 20bTS2ex bTS2en bTS4ex bTS4en Table S8 Activation of Gibbs Free Energies (in kcal/mol), Enthalpies (in kcal/mol) and energies (in kcal/mol) of stationary points of bis reaction computed at gas phase using B3LYP/6-31g (d). Bis reaction TS G G H H E E 25c_TS c _TS Table S9 B3LYP/6-31G(d) optimized cartesian coordinates and the corresponding electronic and free energies for all the reactants and the transition state geometries. 1 E= a.u. G= a.u. C C C C C C H H H H H S O O C C C a E= a.u. G= a.u. C C C C C C H H H H C C C N O O C S14

15 C H H H H C O O C H H C H H H a E= a.u. G= a.u. C C C C C C H H H H C C N H O N C H H H C H H aTS1(1 + 3a) E= a.u. G= a.u. Imaginary Frequency= cm -1 C C C C C C H H H H C C C N O O H H C H H H a E= a.u. G= a.u. C C C C C C H H H C C H C C H H C C O N C H H C H H H aTS2(1 + 3a) E= a.u. G= a.u. Imaginary Frequency= cm -1 C C C C C C H H H H C C C N O O S15

16 C H H C H H H C C C C C C H H H H H S O O C C C C H H H C O O C H H C H H H H aTS3(1 + 3a) E= a.u. G= a.u. Imaginary Frequency= cm -1 C C C C C C H H H H C C C N O O C H H C H H H C H H C H H H C C C C C C H H H H H S O O C C C C H H H C O O C H H C H H H H aTS4(1 + 3a) E= a.u. G= a.u. Imaginary Frequency= cm -1 C C C C C C H H H H C C C N O O C H H C H H H S16

17 C C C C C C H H H H H S O O C C C C H H H C O O C H H C H H H H aTS1(1 + 8a) E= a.u. G= a.u. Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H C O O C H H C H H C C C C C C H H H H H S O O C C C C H H H C O O C H H C H H H H aTS2(1 + 8a) E= a.u. G= a.u. Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H C O O C H H C H H S17

18 H C C C C C C H H H H C C N H O N C H H H C H H H aTS3(1 + 8a) E= a.u. G= a.u Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H C O O C H H C H H H C C C C C C H C C C C C C H H H H C C N H O N C H H H C H H H aTS4(1 + 8a) E= a.u. G= a.u Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H C O O C H H C H H H C C C C C C S18

19 H H H H C C N H O N C H H H C H H H aTS1(1 + 11a) E= a.u. G= a.u. Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H H C O O C H H C H H H C C C C C C H H H C C H H H H H C C N H O N C H H H C H H H aTS2(1 + 11a) E= a.u. G= a.u. Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H H C O O C H H C H H H C C C C C C H H H C C H S19

20 C C H H C C O N C H H C H H H aTS3(1 + 11a) E= a.u. G= a.u Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H H C O O C H H C H H H C C C C C C H H H C C H C C H C C H H C C O N C H H C H H H aTS4(1 + 11a) E= a.u. G= a.u Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H H C O O C H H C H H H C C C C C C H H H C C H C C H S20

21 H C C O N C H H C H H H aTS1(1 + 2a) E= a.u. G= a.u Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H H C O O C H H C H H H C N C H H C C C C C H C H C H H H H C C O N C H H C H H H aTS2(1 + 2a) E= a.u. G= a.u Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H H C O O C H H C H H H C N C H H C C C C C H C H C H H H S21

22 H H H H aTS1(1 + 20a) E= a.u. G= a.u Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H H C O O C H H C H H H C C C C C C H H H H C H N O C H H H F aTS3(1 + 20a) E= a.u. G= a.u Imaginary Frequency= cm -1 C H H H H aTS2(1 + 20a) E= a.u. G= a.u Imaginary Frequency= cm -1 C C C C C C H H H H H S O O C C C C H H H H C O O C H H C H H H C C C C C C H H H H C H N O C H H H F aTS4(1 + 20a) E= a.u. G= a.u Imaginary Frequency= cm -1 C S22

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