Reaction of Lithium Diethylamide with an Alkyl Bromide and Alkyl Benzenesulfonate: Origins of Alkylation, Elimination, and Sulfonation.
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1 Reaction of Lithium Diethylamide with an Alkyl omide and Alkyl Benzenesulfonate: rigins of Alkylation, Elimination, and ulfonation. Lekha Gupta, Antonio Ramírez and David B. Collum* Contribution from the Department of Chemistry and Chemical Biology Baker Laboratory, Cornell University Ithaca, New York upporting Information Page Part 1: Rate tudies I Plot of k obsd vs [TF] for the reaction of n-c (1) with 2 NLi 3 II Plot of k alk vs [TF] for the N-alkylation of 1 with 2 NLi 4 III Plot of k elim vs [TF] for the elimination of 1 with 2 NLi 5 IV Plot of k obsd vs [ 2 NLi] for the reaction of 1 with 2 NLi 6 V Plot of k alk vs [ 2 NLi] for the N-alkylation of 1 with 2 NLi 7 VI Plot of k elim vs [ 2 NLi] for the elimination of 1 with 2 NLi 8 VII Plot of k obsd vs [TF] in 2,2,5,5-4 TF for the reaction of 1 with 9 2 NLi VIII Plot of k alk vs [TF] in 2,2,5,5-4 TF for the N-alkylation of 1 10 with 2 NLi IX Plot of k elim vs [TF] in 2,2,5,5-4 TF for the elimination of 1 11 with 2 NLi X Plot of k obsd vs [TF] for the reaction of n-c Ph (4) with 2 NLi 12 XI Plot of k sulf vs [TF] for the N-sulfonation of 4 with 2 NLi 13 XII Plot of k alk vs [TF] for the N-alkylation of 4 with 2 NLi 14 XIII Plot of k obsd vs [ 2 NLi] in for the reaction of 4 with 2 NLi 15 XIV Plot of k sulf vs [ 2 NLi] for the N-sulfonation of 4 with 2 NLi 16 1
2 XV Plot of k alk vs [ 2 NLi] for the N-alkylation of 4 with 2 NLi 17 Part 2: DFT Computational tudies XVI Relative free energies for the solvation (ΔG, kcal/mol) of 2 NLi 18 Table I ptimized geometries for the serial solvation of 2 NLi 19 XVII Free energies and enthalpies of activation for the reaction of 24 with 2 NLi calculated using B3LYP level of theory with 6-31G(d)-VP basis set XVIII Free energies of activation for the reaction of with 2 NLi 25 calculated using single point MP2 corrections to B3LYP/6-31G(d)- VP optimized structures Table II ptimized geometries of reactants and transition structures for the reaction of with 2 NLi 26 XIX Free energies and enthalpies of activation for the reaction of 31 2 Ph with 2 NLi calculated using B3LYP level of theory with 6-31G(d)-VP basis set XX Free energies of activation for the reaction of 2 Ph with 2 NLi 32 calculated using single point MP2 corrections to B3LYP/6-31G(d)- VP optimized structures Table III ptimized geometries of reactants and transition structures for the reaction of 2 Ph with 2 NLi 33 Complete Reference: (18) All calculations were performed with Gaussian 03, Revision B.04, Frisch, M. J.; Trucks, G. W.; chlegel,. B.; cuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar,..; Tomasi, J.; Barone, V.; nnucci, B.; Cossi, M.; calmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji,.; ada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; asegawa, J.; Ishida, M.; Nakajima, T.; onda, Y.; Kitao,.; Nakai,.; Klene, M.; Li, X.; Knox, J. E.; ratchian,. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; tratmann, R. E.; Yazyev,.; Austin, A. J.; Cammi, R.; Pomelli, C.; chterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; alvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich,.; Daniels, A. D.; train, M. C.; Farkas,.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; rtiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford,.; Cioslowski, J.; tefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A.; Gaussian, Inc., Wallingford CT,
3 Part 1: Rate tudies n-c NLi TF/toluene 0 o C n-c N 2 + n-c I. Plot of k obsd vs [TF] in toluene cosolvent for the reaction of 1 (0.004 M) with 2 NLi (0.10 M) at 0 C. The curve depicts an unweighted least-squares fit to k obsd = k[tf] n (k = ( ) x 10-4, n = ). [TF] (M) k obsd 1 x 10 3 (s -1 ) k obsd 2 x 10 3 (s -1 ) k obsd avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E-1 3
4 n-c NLi TF/toluene 0 o C n-c N 2 + n-c II. Plot of k alk vs [TF] in toluene cosolvent for the N-alkylation of 1 (0.004 M) with 2 NLi (0.10 M) at 0 C. The curve depicts an unweighted least-squares fit to k alk = k[tf] n (k = ( ) x 10-4, n = ). [TF] (M) k alk 1 x 10 3 (s -1 ) k alk 2 x 10 3 (s -1 ) k alk avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E-1 4
5 n-c NLi TF/toluene 0 o C n-c N 2 + n-c III. Plot of k elim vs [TF] in toluene cosolvent for the elimination of 1 (0.004 M) with 2 NLi (0.10 M) at 0 C. The curve depicts an unweighted least-squares fit to k elim = k[tf] n (k = (6 + 2) x 10-6, n = ). [TF] (M) k elim 1 x 10 3 (s -1 ) k elim 2 x 10 3 (s -1 ) k elim avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E-2 5
6 n-c NLi TF/toluene 0 o C n-c N 2 + n-c IV. Plot of k obsd vs [ 2 NLi] in TF (3.9 M) and toluene cosolvent for the reaction of 1 (0.004 M) with 2 NLi at 0 C. The curve depicts an unweighted least-squares fit to k obsd = k[ 2 NLi] n (k = ( ) x 10-3, n = ). [ 2 NLi] (M) k obsd 1 x 10 3 (s -1 ) k obsd 2 x 10 3 (s -1 ) k obsd avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E E E E E E E-1 6
7 n-c NLi TF/toluene 0 o C n-c N 2 + n-c V. Plot of k alk vs [ 2 NLi] in TF (3.9 M) and toluene cosolvent for the N- alkylation of 1 (0.004 M) with 2 NLi at 0 C. The curve depicts an unweighted least-squares fit to k alk = k[ 2 NLi] n (k = ( ) x 10-3, n = ). [ 2 NLi] (M) k alk 1 x 10 3 (s -1 ) k alk 2 x 10 3 (s -1 ) k alk avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E E E E E E E-2 7
8 n-c NLi TF/toluene 0 o C n-c N 2 + n-c VI. Plot of k elim vs [ 2 NLi] in TF (3.9 M) and toluene cosolvent for the elimination of 1 with 2 NLi (0.004 M) at 0 C. The curve depicts an unweighted least-squares fit to k elim = k[ 2 NLi] n (k = ( ) x 10-4, n = ). [ 2 NLi] (M) k elim 1 x 10 3 (s -1 ) k elim 2 x 10 3 (s -1 ) k elim avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E E E E E E E-3 8
9 n-c NLi TF/toluene 0 o C n-c N 2 + n-c VII. Plot of k obsd vs [TF] in 2,2,5,5-4 TF cosolvent for the reaction of 1 (0.004 M) with 2 NLi (0.10 M) at 0 C. The curve depicts an unweighted least-squares fit to k obsd = k[tf] n (k = ( ) x 10-4, n = ). [TF] (M) k obsd 1 x 10 3 (s -1 ) k obsd 2 x 10 3 (s -1 ) k obsd avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E-1 9
10 n-c NLi TF/toluene 0 o C n-c N 2 + n-c VIII. Plot of k alk vs [TF] in 2,2,5,5-tetramethyltetrahydrofuran cosolvent for the N-alkylation of 1 (0.004 M) with 2 NLi (0.10 M) at 0 C. The curve depicts an unweighted least-squares fit to k alk = k[tf] n (k = ( ) x 10-4, n = ). [TF] (M) k alk 1 x 10 3 (s -1 ) k alk 2 x 10 3 (s -1 ) k alk avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E-1 10
11 n-c NLi TF/toluene 0 o C n-c N 2 + n-c IX. Plot of k elim vs [TF] in 2,2,5,5-tetramethyltetrahydrofuran cosolvent for the elimination of 1 (0.004 M) with 2 NLi (0.10 M) at 0 C. The curve depicts an unweighted least-squares fit to k elim = k[tf] n (k = ( ) x 10-5, n = ). [TF] (M) k elim 1 x 10 3 (s -1 ) k elim 2 x 10 3 (s -1 ) k elim avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E-2 11
12 n-c Ph 2 NLi TF/toluene 2 N 2 Ph + n-c 7 15 N 2-30 o C X. Plot of k obsd vs [TF] in toluene cosolvent for the reaction of 4 (0.004 M) with 2 NLi (0.10 M) at -30 C. The curve depicts an unweighted least-squares fit to k obsd = c[tf] + k (c = ( ) x 10-5, k = ( ) x 10-3 ). [TF] (M) k obsd 1 x 10 3 (s -1 ) k obsd 2 x 10 3 (s -1 ) k obsd avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E-2 12
13 n-c Ph 2 NLi TF/toluene 2 N 2 Ph + n-c 7 15 N 2-30 o C XI. Plot of k sulf vs [TF] in toluene cosolvent for the N-sulfonation of 4 (0.004 M) with 2 NLi (0.10 M) at -30 C. The curve depicts an unweighted least-squares fit to k obsd = c[tf] + k (c = ( ) x 10-4, k = ( ) x 10-3 ). [TF] (M) k sulf 1 x 10 3 (s -1 ) k sulf 2 x 10 3 (s -1 ) k sulf avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E-2 13
14 n-c Ph 2 NLi TF/toluene 2 N 2 Ph + n-c 7 15 N 2-30 o C XII. Plot of k alk vs [TF] in toluene cosolvent for the N-alkylation of 4 (0.004 M) with 2 NLi (0.10 M) at -30 C. The curve depicts an unweighted least-squares fit to k alk = k[tf] n (k = ( ) x 10-6, n = ). [TF] (M) k alk 1 x 10 3 (s -1 ) k alk 2 x 10 3 (s -1 ) k alk avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E-3 14
15 n-c Ph 2 NLi TF/toluene 2 N 2 Ph + n-c 7 15 N 2-30 o C XIII. Plot of k obsd vs [ 2 NLi] in TF (6.0 M) and toluene cosolvent for the reaction of 4 (0.004 M) with 2 NLi at -30 C. The curve depicts an unweighted least-squares fit to k obsd = k[ 2 NLi] n (k = ( ) x 10-2, n = ). [ 2 NLi] (M) k obsd 1 x 10 3 (s -1 ) k obsd 2 x 10 3 (s -1 ) k obsd avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E E E E E E E-1 15
16 n-c Ph 2 NLi TF/toluene 2 N 2 Ph + n-c 7 15 N 2-30 o C XIV. Plot of k sulf vs [ 2 NLi] in TF (6.0 M) and toluene cosolvent for the N- sulfonation of 4 (0.004 M) with 2 NLi at -30 C. The curve depicts an unweighted least-squares fit to k sulf = k[ 2 NLi] n (k = ( ) x 10-2, n = ). [ 2 NLi] (M) k sulf 1 x 10 3 (s -1 ) k sulf 2 x 10 3 (s -1 ) k sulf avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E E E E E E E-1 16
17 n-c Ph 2 NLi TF/toluene 2 N 2 Ph + n-c 7 15 N 2-30 o C XV. Plot of k alk vs [ 2 NLi] in TF (6.0 M) and toluene cosolvent for the N- alkylation of 4 (0.004 M) with 2 NLi at -30 C. The curve depicts an unweighted least-squares fit to k alk = k[ 2 NLi] n (k = ( ) x 10-4, n = ). [ 2 NLi] (M) k alk 1 x 10 3 (s -1 ) k alk 2 x 10 3 (s -1 ) k alk avg x 10 3 (s -1 ) E E E E E E E E E E E E E E E E E E E E E E E
18 Part 2: DFT Computational tudies N Li Li N 0.0 N Li Li N -8.1 N Li Li N N Li Li N XVI. Relative free energies for the solvation (ΔG, kcal/mol) of 2 NLi with TF ( = TF) calculated using B3LYP level of theory with 6-31G(d) basis set at -90 C. 18
19 Table I. ptimized geometries at B3LYP level of theory with 6-31G(d) basis set for the serial solvation of 2 NLi with TF with free energies (G, artrees) and cartesian coordinates (X, Y, Z) at -90 C. G = (-90 C) Atom X Y Z Atom X Y Z C C C C N Li Li N G = (-90 C) = TF Atom X Y Z Atom X Y Z N C C Li Li N C C C C C C
20 Table I (Continued). N Li Li N G = (-90 C) = TF Atom X Y Z Atom X Y Z Li C C C C N C C Li N C C C C C C C C C C
21 Table I (Continued). N Li Li N G = (-90 C) = TF Atom X Y Z Atom X Y Z Li N Li N C C C C C C C C C C C C C C C C C C C C
22 Table I (Continued). N Li Li N G = (-90 C) = TF Atom X Y Z Atom X Y Z Li C C C C C C C C N C C C C Li N C C C C C C C C
23 C C C C
24 2 N Li 3 Li 3 N (+18.9) (12) (+16.8) (11) Li 2 N C (+13.0) (10) /2 N Li N Li + 3 C XVII. Free energies of activation (ΔG, kcal/mol) for the reaction of with 2 NLi calculated using B3LYP level of theory with VP basis set for and 6-31G(d) basis set for the rest of atoms at 25 C ( = 2 ). Values in parentheses correspond to the enthalpies of activation (Δ, kcal/mol). 24
25 2 N Li (12) Li 3 N (11) Li 2 N C (10) + 2 1/2 N Li N Li + 3 C XVIII. Free energies of activation (ΔG, kcal/mol) for the reaction of with 2 NLi calculated using single point MP2 corrections to B3LYP/6-31G(d)-VP optimized structures at 25 C ( = 2 ). 25
26 Table II. ptimized geometries of reactants and transition structures calculated at B3LYP level of theory using VP basis set for and 6-31G(d) basis set for the rest of atoms, for the reaction of with 2 NLi, with free energies (G, artrees), enthalpies (, artrees), and cartesian coordinates (X,Y,Z) at 25 C. (Note: G MP2 includes single point MP2 corrections to B3LYP/6-31G(d)-VP optimized structures) N Li N Li G = = G MP2 = = 2 Atom X Y Z Atom X Y Z N C C Li Li N C C C C C C
27 Table II (Continued). 3 C G = = G MP2 = Atom X Y Z C C C C 3 G = = G MP2 = Atom X Y Z C C
28 Table II (Continued). 3 Li 2 N C 3 G = = G MP2 = = 2 Atom X Y Z Atom X Y Z C C N C C Li C C C C C C
29 Table II (Continued). N Li 3 G = = G MP2 = = 2 Atom X Y Z Atom X Y Z C C N C C Li C C C C C C
30 Table II (Continued). 2 N Li 3 G = = G MP2 = = 2 Atom X Y Z Atom X Y Z N C C Li C C C C C C C C
31 2 N Li 3 2 Ph (+17.9) (17) Li 3 N Ph (16.8) (16) 3 Li Ph 2 N C (+12.3) (14) Li N Li Ph N (+3.1) (15) -1/2 ( 2 NLi) /2 ( 2 NLi) Li Ph 2 N C (+15.5) (13) -1/2 ( 2 NLi) N Li N Li + 3 C 2 Ph XIX. Free energies of activation (ΔG, kcal/mol) for the reaction of 2 Ph with 2 NLi calculated using B3LYP level of theory with VP basis set for and 6-31G(d) basis set for the rest of atoms at 25 C ( = 2 ). Values in parentheses correspond to the enthalpies of activation (Δ, kcal/mol). 31
32 2 N Li 3 2 Ph (17) Li 3 N Ph (16) 3 Li 2 N C (14) Ph Li N Li Ph N (15) -1/2 ( 2 NLi) /2 ( 2 NLi) Li 2 N C (13) -1/2 ( 2 NLi) Ph N Li N Li + 3 C 2 Ph XX. Free energies of activation (ΔG, kcal/mol) for the reaction of 2 Ph with 2 NLi calculated using single point MP2 corrections to B3LYP/6-31G(d)-VP optimized structures at 25 C ( = 2 ). 32
33 Table III. ptimized geometries of reactant and transition structure calculated at B3LYP level of theory using VP basis set for and 6-31G(d) basis set for the rest of atoms, for the reaction of 2 Ph with 2 NLi, with free energies (G, artrees), enthalpies (, artrees) and cartesian coordinates (X,Y,Z) at 25 C. (Note: G MP2 includes single point MP2 corrections to B3LYP/6-31G(d)-VP optimized structures) 3 C Ph G = = G MP2 = Atom X Y Z Atom X Y Z C C C C C C C C
34 Table III (Continued). 2 Li 2 N Ph (13) G = = G MP2 = = 2 C 3 Atom X Y Z Atom X Y Z C C N C C Li C C C C C C C C C C
35 Table III (Continued). 3 Li 2 N Ph (14) G = = G MP2 = = 2 C 3 Atom X Y Z Atom X Y Z Li N C C C C C C C C C C C C C C C C
36 Table III (Continued). Ph Li N Li N (15) G = = G MP2 = = 2 Atom X Y Z Atom X Y Z Li Li N C C N C C C C C C C C C C C C C C
37 Table III (Continued). N Li 3 Ph (16) G = = G MP2 = = 2 Atom X Y Z Atom X Y Z C C N Li C C C C C C C C C C C C C C
38 Table III (Continued). 2 N Li 3 2 Ph (17) G = = G MP2 = = 2 Atom X Y Z Atom X Y Z C C C C Li N C C C C C C C C C C C C
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