An Acyclic Trialkylamine Virtually Planar at Nitrogen. Some Chemical Consequences of Nitrogen Planarity.
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1 Page 1 of 18 An Acyclic Trialkylamine Virtually Planar at Nitrogen. Some Chemical Consequences of Nitrogen Planarity. Yuanping Jie, Peter Livant,* Hui Li, Minmin Yang, Wei Zhu, Vince Cammarata, Phillip Almond, Tyler Sullens, Yu Qin, Eric Bakker Department of Chemistry and Biochemistry, Auburn University, Auburn, Alabama Supporting Information Table of Contents Figure S1. ORTEP drawing of compound Figure S2. ORTEP drawing of compound 9H + Cl...3 Figure S3. H-bonding contacts involving Cl in 9H + Cl...4 Figure S4. 1 H NMR Spectrum of Figure S5. 1 H NMR Spectrum of Figure S6. 13 C NMR Spectrum of Figure S7. 1 H NMR Spectrum of Figure S8. 13 C NMR Spectrum of Figure S9. DEPT-135 NMR Spectrum of Figure S10. 1 H NMR Spectrum of Figure S11. Expanded 1 H NMR Spectrum of Figure S C NMR Spectrum of Figure S13. 1 H NMR Spectrum of Figure S C NMR and DEPT-135 Spectra of Figure S15. 1 H NMR Spectrum of 9H + Cl...16 Figure S C NMR and DEPT-135 Spectra of 9H + Cl...17 Table S1. Effect on 15 N chemical shift of one N-C-CH 3 N-C-CH 2 OH transformation, A...18
2 Figure S1. ORTEP plot of 9 at the 50% probability level Page 2 of 18
3 Figure S2. ORTEP plot of 9H + Cl at the 50% probability level Page 3 of 18
4 Page 4 of 18 Figure S3. H-bonding contacts involving Cl in 9H + Cl. Atoms are represented by spheres of arbitrary size. Hydrogens bonded to carbon have been omitted.
5 Figure S4. 1 H-NMR spectrum of 13. (400 MHz; CDCl 3 ) Page 5 of 18
6 Figure S5. 1 H-NMR spectrum of 16. (400 MHz; CDCl 3 ) Page 6 of 18
7 Figure S6. 13 C-NMR spectrum of 16. (100 MHz; CDCl 3 ) Page 7 of 18
8 Figure S7. 1 H-NMR spectrum of 17. (400 MHz; CDCl 3 ) Page 8 of 18
9 Figure S8. 13 C-NMR spectrum of 17. (100 MHz; CDCl 3 ) Page 9 of 18
10 Figure S9. 13 C-DEPT-135 spectrum of 17. (100 MHz; CDCl 3 ) Page 10 of 18
11 Page 11 of 18 Figure S10. 1 H-NMR spectrum of 9. (400 MHz; D 2 O) Methanol, added as a chemical shift standard, appears at 3.34 ppm.
12 Page 12 of 18 Figure S11. Expanded 1 H-NMR spectrum of 9. (400 MHz; D 2 O) The spectrum has been resolution-enhanced by Gaussian multiplication. Added methanol appears at 3.34 ppm.
13 Page 13 of 18 Figure S C-NMR spectrum of 9. (100 MHz; D 2 O) Methanol was added to provide a chemical shift standard (49.5 ppm).
14 Figure S13. 1 H NMR Spectrum of 18. (400 MHz; CDCl 3 ) Page 14 of 18
15 Figure S C NMR and DEPT-135 Spectra of 18. (100 MHz; CDCl 3 ) Page 15 of 18
16 Page 16 of 18 Figure S15. 1 H-NMR Spectrum of 9H + Cl. (400 MHz; D 2 O). Methanol, added as a chemical shift standard, appears at 3.34 ppm.
17 Page 17 of 18 Figure S C and DEPT-135 Spectra of 9H + Cl. (100 MHz; D 2 O). Methanol, added as a chemical shift standard, appears at 49.5 ppm.
18 Page 18 of 18 Table S1. Effect on 15 N chemical shift of one N-C-CH 3 N-C-CH 2 OH transformation, A Entry 1 2 Amine Š355.4 (CH NH 3 OH) a Š365.7 (no solvent) b HO 2 NH Š Š355.1 (cyclohexane) a Š361.7 (no solvent) c Š363.5 (no solvent) d NH 2 Š338.1 (CH 3 OH) a NH 2 HO Š337.2 (cyclohexane) a β-hydroxyamine Š346.0 (no solvent) b A (ppm) Š NH 2 Š324.3 (CH 3 OH) a NH 2 HO Š322.4 (cyclohexane) a Š332.9 (no solvent) b Š NH 2 Š342.2 (CH 3 OH) a HO NH 2 Š342.4 (cyclohexane) a Š351.0 (no solvent) b Š8.7 5 N H Š334.0 (no solvent) b HO NH 2 Š351.4 (no solvent) d Š8.7 6 Š332.0 (CH N 3 OH) a HO Š6.55 Š333.6 (cyclohexane) a N Š345.9 (no solvent) d 2 7 HO N 2 Š345.9 (no solvent) d HO N 3 Š354.0 (no solvent) d Š352.3 (D 2 O) e Š N Š340.5 (CH 3 OH) a Š343.1 (cyclohexane) a HO N 2 Š353.2 (no solvent) d Š5.7 9 N Š351.3 (CH 3 OH) a Š355.2 (cyclohexane) a HO N Š358.0 (no solvent) d Š4.75 Average A = Š7.4 ± 1.5 ppm a Duthaler, R. O.; Roberts, J. D. J. Am. Chem. Soc. 1978, 100, b Lichter, R. L.; Roberts, J. D. J. Am. Chem. Soc. 1972, 94, c Levy, G. C.; Holloway, C. E.; Rosanske, R. C.; Hewitt, J. M.; Bradley, C. H. Org. Magn. Reson. 1976, 8, d Liepins, E.; Birgele, I.; Zelcans, G.; Urtane, I.; Lukevics, E. Zh. Obshch. Khim. 1980, 50, e This work. Note: Each A value was obtained by subtracting the average of all chemical shift entries for the amine from the average of all chemical shift entries for the corresponding β-hydroxylamine and dividing by the number of β methyls altered.
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