Dynamic Exchange in Intramolecular Lewis Pairs with Multiple Lewis-acidic Functions
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1 Dynamic Exchange in Intramolecular Lewis Pairs with Multiple Lewis-acidic Functions Leif A. Körte, Sebastian Blomeyer, Jan-Hendrik Peters, Andreas Mix, Beate Neumann, Hans-Georg Stammler and Norbert W. Mitzel Lehrstuhl für Anorganische Chemie und Strukturchemie und Centrum für Molekulare Materialien CM 2, Fakultät für Chemie, Universität Bielefeld, Universitätstraße 25, Bielefeld (Germany) N,N-Diallyl-N-methylamine (2) Additional Spectra Figure S1. 1 H NMR spectrum (500 MHz, CDCl 3 ) of N,N-diallyl-N-methylamine (2). Figure S2. 13 C{ 1 H} NMR spectrum (126 MHz, CDCl 3 ) of N,N-diallyl-N-methylamine (2).
2 Diallylmethylphosphane (4) Figure S3. 1 H NMR spectrum (300 MHz, C 6 D 6 ) of diallylmethylphosphane (4). Figure S4. 13 C{ 1 H} NMR spectrum (76 MHz, C 6 D 6 ) of diallylmethylphosphane (4). Figure S5. 31 P{ 1 H} NMR spectrum (121 MHz, C 6 D 6 ) of diallylmethylphosphane (4).
3 Me 2 N-CH 2 -CH 2 -CH 2 -BBN (6) Figure S6. 1 H NMR spectrum (500 MHz, Tol-d 8, 373 K) of Me 2 N-CH 2 -CH 2 -CH 2 -BBN (6). Figure S7. 11 B NMR spectrum (192 MHz, Tol-d 8, 383 K) of Me 2 N-CH 2 -CH 2 -CH 2 -BBN (6). Figure S8. 13 C{ 1 H} NMR spectrum (126 MHz, Tol-d 8, 373 K) of Me 2 N-CH 2 -CH 2 -CH 2 -BBN (6).
4 MeN-(CH 2 -CH 2 -CH 2 -BBN) 2 (7) For 11 B NMR spectra see main paper. Figure S9. 1 H NMR spectrum (600 MHz, Tol-d 8, 363 K) of MeN(CH 2 -CH 2 -CH 2 -BBN) 2 (7). Due to fast exchange only one set of signals can be observed for both (CH 2 ) 3 BBN side arms. During the measurement decomposition at high temperature, probably by dehydroboration occurs. Therefore, some signals of decomposition products can be observed. Figure S C{ 1 H} NMR spectrum (126 MHz, Tol-d 8, 373 K) of MeN(CH 2 -CH 2 -CH 2 -BBN) 2 (7). Due to fast exchange only one set of signals can be observed for both (CH 2 ) 3 BBN side arms. During the measurement decomposition at high temperature, probably by dehydroboration occurs. Therefore, many signals of decomposition products can be observed. Figure S C{ 1 H} NMR spectrum (126 MHz, C 6 D 6, 298 K) of MeN(CH 2 -CH 2 -CH 2 -BBN) 2 (7). Due to dynamic exchange at ambient temperature the resonances are broadened and not all expected resonances can be observed.
5 N-(CH 2 -CH 2 -CH 2 -BBN) 3 (9) For 11 B NMR see VT-NMR spectra in the main paper. Figure S12. 1 H NMR spectrum (300 MHz, C 6 D 6, 298 K) of N(CH 2 -CH 2 -CH 2 -BBN) 3 (9). Figure S C{ 1 H} NMR spectrum (76 MHz, C 6 D 6, 298 K) of N(CH 2 -CH 2 -CH 2 -BBN) 3 (9). MeP-(CH 2 -CH 2 -CH 2 -BBN) 2 (10) For 11 B NMR see VT-NMR spectra in the main paper. Figure S14. 1 H NMR spectrum (500 MHz, C 6 D 6, 298 K) of MeP(CH 2 -CH 2 -CH 2 -BBN) 2 (10).
6 Figure S15. 1 H NMR spectrum (500 MHz, Tol-d 8, 393 K) of MeP(CH 2 -CH 2 -CH 2 -BBN) 2 (10). Due to a severe overlap of the resonances no assignment was possible, even when measured at elevated temperature. Figure S C{ 1 H} DEPT-135 NMR spectrum (76 MHz, Tol-d 8, 393 K) of MeP(CH 2 -CH 2 -CH 2 -BBN) 2 (10). Due to a severe overlap of the resonances in the 1 H NMR spectra as well as line broadening due to the exchange of the boron Lewis acids no assignment of all resonances was possible. Figure S P{ 1 H} NMR spectrum (202 MHz, C 6 D 6, 298 K) of MeP(CH 2 -CH 2 -CH 2 -BBN) 2 (10).
7 Crystallographic data: Table S1. Crystallographic data of compounds 6, 7 and 9. Empirical formula C 13 H 26 BN C 23 H 43 B 2 N C 33 H 60 B 3 N M r F(000) Crystal system monoclinic monoclinic triclinic Space group P2 1 /n P2 1 /c P1 a [Å] (2) (5) (7) b [Å] (2) (2) (2) c [Å] (2) (4) (2) α [ ] (1) β [ ] (2) (4) (8) γ [ ] (9) V [Å 3 ] (4) (1) (3) Z ρ calcd. [g cm 3 ] μ [mm 1 ] θ max [ ] Index range h 11 h h 18, 10 h 10, Index range k 15 k k k 16 Index range l 13 l l l 17 Refl. collect Indep. refl R int Observed refl., I>2σ(I) Parameters R 1, I>2σ(I) wr 2, I>2σ(I) R 1 (all data) wr 2 (all data) GoF ρ max/min [e Å 3 ] 0.33/ / / 0.28 CCDC-No
8 Computational details E(PW6B95-D3BJ(abc)/def2-TZVP//PBEh-3c) + δ thermo(pbeh-3c) + δ solvation(pw6b95-d3bj(abc)/def2-tzvp/cosmo(toluene)//pbeh-3c) closed-7 Figure S18. Calculated structure of closed kj mol kj mol kj mol kj mol 1
9 open-7 Figure S19. Calculated structure of open kj mol kj mol kj mol kj mol 1 TS-7 Figure S20. Calculated structure of TS-7. ṽ imag = kj mol kj mol kj mol kj mol cm 1
10 closed-10 Figure S21. Calculated structure of closed kj mol kj mol kj mol kj mol 1 open-10 Figure S22. Calculated structure of open kj mol kj mol kj mol kj mol 1
11 TS-10 Figure S23. Calculated structure of TS-10. ṽ imag = kj mol kj mol kj mol kj mol cm 1
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