The Effect of Substituents on Indirect Nuclear Spin-Spin Coupling Constants: Methan- and Ethanimine, Methanal- and Ethanaloxime
Abstract
:Introduction
Computational Aspects
- The RCN bond length is close to 128 pm in all molecules.
- The substituent -OH leads to an increase of the angle by ~ 5° and to a decrease of the and angles by 2° to 3°.
- The C=N-Z group is roughly rigid with respect to both its internal distances and angles.
Results
Coupling | Molecule | KOD | KOP | KSD | KFC | K | J | Jexpt. |
C-15N | methanimine | 0.04 | -28.07 | 4.59 | 30.75 | 7.30 | -2.23 | |
(Z)-ethanimine | 0.11 | -26.70 | 4.49 | 28.51 | 6.41 | -1.96 | ||
(E)-ethanimine | 0.11 | -27.02 | 4.40 | 33.16 | 10.65 | -3.26 | ||
methanaloxime | 0.14 | -26.71 | 8.20 | 30.62 | 12.25 | -3.75 | |2.96| [68]a | |
(Z)-ethanaloxime | 0.21 | -26.68 | 7.69 | 27.88 | 9.10 | -2.79 | |2.3| [68]a | |
(E)-ethanaloxime | 0.21 | -26.34 | 7.99 | 32.59 | 14.46 | -4.43 | |4.0| [68]a | |
15N-HZ | methanimine | 0.11 | 0.43 | -0.14 | 40.15 | 40.55 | -49.39 | |
(Z)-ethanimine | 0.15 | 0.72 | -0.13 | 39.45 | 40.19 | -48.95 | ||
(E)-ethanimine | 0.14 | 0.71 | -0.11 | 40.92 | 41.65 | -50.73 | ||
C-HX | methanimine | 0.16 | -0.12 | 0.04 | 56.80 | 56.89 | 171.86 | 172.9 [65] |
(Z)-ethanimine | 0.25 | -0.19 | 0.03 | 55.08 | 55.17 | 166.68 | ||
methanaloxime | 0.20 | -0.01 | -0.01 | 58.72 | 58.90 | 177.95 | ||
(Z)-ethanaloxime | 0.28 | -0.09 | -0.02 | 57.77 | 57.94 | 175.05 | 177 ± 1 [69] | |
C-HY | methanimine | 0.16 | -0.09 | 0.05 | 52.86 | 52.99 | 160.07 | 163.7 [66] |
(E)-ethanimine | 0.25 | -0.18 | 0.04 | 51.66 | 51.77 | 156.41 | ||
methanaloxime | 0.22 | -0.04 | 0.03 | 55.60 | 55.81 | 168.60 | ||
(E)-ethanaloxime | 0.30 | -0.12 | 0.02 | 54.47 | 54.66 | 165.14 | 163 ± 1 [69] | |
C-CX | (E)-ethanimine | 0.22 | -1.64 | 0.97 | 63.51 | 63.06 | 47.92 | |
(E)-ethanaloxime | 0.24 | -1.35 | 0.93 | 67.94 | 67.76 | 51.49 | 48.42 [69] | |
C-CY | (Z)-ethanimine | 0.22 | -1.56 | 0.98 | 51.72 | 51.36 | 39.02 | |
(Z)-ethanaloxime | 0.26 | -1.43 | 0.92 | 57.18 | 56.92 | 43.25 | 40.51 [69] |
Triplet instabilities and quasi-instabilities
Coupling | Molecule | Angles in H2C=N | KOD | KOP | KSD | KFC | K |
1K(C,N) | H2C=NH | Optimized | 0.04 | -28.07 | 4.59 | 30.75 | 7.30 |
from H2C=NOH | 0.03 | -28.63 | 4.47 | 30.26 | 6.17 | ||
H2C=NOH | Optimized | 0.14 | -26.71 | 8.20 | 30.62 | 12.25 | |
from H2C=NH | -0.13 | -26.28 | 8.32 | 31.50 | 13.68 | ||
1K(C,HX) | H2C=NH | Optimized | 0.16 | -0.12 | 0.04 | 56.80 | 56.89 |
from H2C=NOH | 0.16 | -0.13 | 0.04 | 58.08 | 58.16 | ||
H2C=NOH | Optimized | 0.20 | -0.01 | -0.01 | 58.72 | 58.90 | |
from H2C=NH | 0.20 | -0.00 | -0.01 | 57.66 | 57.84 | ||
1K(C,HY) | H2C=NH | Optimized | 0.16 | -0.09 | 0.05 | 52.86 | 52.99 |
from H2C=NOH | 0.17 | -0.09 | 0.05 | 53.73 | 53.86 | ||
H2C=NOH | Optimized | 0.22 | -0.04 | 0.03 | 55.60 | 55.81 | |
from H2C=NH | 0.21 | -0.03 | 0.03 | 54.81 | 55.02 | ||
2K(N,HX) | H2C=NH | Optimized | -0.24 | -1.14 | 0.12 | 8.78 | 7.52 |
from H2C=NOH | -0.23 | -1.18 | 0.13 | 7.77 | 6.49 | ||
H2C=NOH | Optimized | -0.17 | -1.13 | 0.05 | 11.10 | 9.85 | |
From H2C=NH | -0.18 | -1.09 | 0.04 | 12.09 | 10.85 | ||
2K(N,HY) | H2C=NH | Optimized | -0.29 | -0.85 | 0.19 | -2.80 | -3.75 |
From H2C=NOH | -0.28 | -0.93 | 0.19 | -2.36 | -3.37 | ||
H2C=NOH | Optimized | -0.23 | -0.99 | 0.06 | -1.74 | -2.90 | |
From H2C=NH | -0.25 | -0.89 | 0.07 | -1.94 | -3.00 | ||
3K(HX,HY) | H2C=NH | Optimized | -0.31 | 0.31 | 0.03 | 1.27 | 1.31 |
From H2C=NOH | -0.34 | 0.34 | 0.02 | 1.74 | 1.77 | ||
H2C=NOH | Optimized | -0.32 | 0.34 | 0.02 | 0.66 | 0.69 | |
From H2C=NH | -0.05 | 0.31 | 0.03 | 0.23 | 0.28 |
Coupling | Molecule | KOD | KOP | KSD | KFC | K | J | Jexpt. |
15N-HX | methanimine | -0.24 | -1.14 | 0.12 | 8.78 | 7.52 | -9.16 | |
(Z)-ethanimine | -0.20 | -1.01 | 0.10 | 10.04 | 8.93 | -10.88 | ||
methanaloxime | -0.17 | -1.13 | 0.05 | 11.10 | 9.85 | -12.00 | -13.88 [67]a | |
(Z)-ethanaloxime | -0.12 | -1.09 | 0.07 | 12.38 | 11.23 | -13.68 | -15.93 [67]b | |
15N-HY | methanimine | -0.29 | -0.85 | 0.19 | -2.80 | -3.75 | 4.56 | |
(E)-ethanimine | -0.25 | -0.84 | 0.14 | -2.84 | -3.80 | 4.63 | ||
methanaloxime | -0.23 | -0.99 | 0.06 | -1.74 | -2.90 | 3.53 | 2.68 [67]a | |
(E)-ethanaloxime | -0.19 | -1.05 | 0.02 | -2.08 | -3.30 | 4.02 | 2.93 [67]b | |
15N-CX | (E)-ethanimine | -0.10 | -1.33 | 0.10 | 31.39 | 30.06 | -9.21 | |
(E)-ethanaloxime | -0.05 | -0.44 | 0.13 | 31.91 | 31.55 | -9.67 | |9.0| [68]c | |
15N-CY | (Z)-ethanimine | -0.14 | -2.27 | 0.11 | -11.72 | -14.01 | 4.29 | |
(Z)-ethanaloxime | -0.10 | -1.54 | -0.05 | -4.98 | -6.68 | 2.05 | |1.8| [68]c | |
C-HZ | methanimine | -0.26 | -0.86 | -0.02 | -3.58 | -4.72 | -14.26 | -13.1 [65] |
(Z)-ethanimine | -0.21 | -0.90 | -0.03 | -3.40 | -4.55 | -13.74 | ||
(E)-ethanimine | -0.22 | -0.87 | -0.03 | -3.01 | -4.12 | -12.46 | ||
CY-HX | (Z)-ethanimine | -0.12 | 0.06 | 0.01 | 5.00 | 4.94 | 14.94 | |
(Z)-ethanaloxime | -0.13 | 0.08 | 0.01 | 2.58 | 2.54 | 7.68 | ||
CX-HY | (E)-ethanimine | -0.12 | 0.05 | 0.01 | 4.47 | 4.42 | 13.34 | |
(E)-ethanaloxime | -0.13 | 0.09 | 0.01 | 2.72 | 2.69 | 8.14 | ||
HX-HY | Methanimine | -0.31 | 0.31 | 0.03 | 1.27 | 1.31 | 15.76 | 17.6 [65] |
methanaloxime | -0.32 | 0.34 | 0.02 | 0.66 | 0.69 | 8.33 |
Coupling | Molecule | KOD | KOP | KSD | KFC | K | J | Jexpt. |
cis-CY-HZ | (Z)-ethanimine | -0.01 | -0.07 | -0.02 | 3.84 | 3.74 | 11.30 | |
trans-CX-HZ | (E)-ethanimine | -0.23 | 0.19 | 0.02 | 5.55 | 5.52 | 16.69 | |
cis-HY-HZ | Methanimine | -0.07 | 0.02 | 0.01 | 1.53 | 1.48 | 17.80 | 17.0 [65] |
(E)-ethanimine | -0.04 | -0.01 | 0.01 | 1.33 | 1.30 | 15.66 | ||
trans-HX-HZ | Methanimine | -0.37 | 0.31 | 0.03 | 2.03 | 2.00 | 24.06 | 25.2 [65] |
(Z)-ethanimine | -0.36 | 0.30 | 0.03 | 1.95 | 1.92 | 23.08 |
One-bond coupling
Two-bond coupling
Three-bond coupling
Conclusions
Acknowledgments
References and Notes
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Provasi, P.F.; Aucar, G.A.; Sauer, S.P.A. The Effect of Substituents on Indirect Nuclear Spin-Spin Coupling Constants: Methan- and Ethanimine, Methanal- and Ethanaloxime. Int. J. Mol. Sci. 2003, 4, 231-248. https://doi.org/10.3390/i4040231
Provasi PF, Aucar GA, Sauer SPA. The Effect of Substituents on Indirect Nuclear Spin-Spin Coupling Constants: Methan- and Ethanimine, Methanal- and Ethanaloxime. International Journal of Molecular Sciences. 2003; 4(4):231-248. https://doi.org/10.3390/i4040231
Chicago/Turabian StyleProvasi, Patricio F., Gustavo A. Aucar, and Stephan P. A. Sauer. 2003. "The Effect of Substituents on Indirect Nuclear Spin-Spin Coupling Constants: Methan- and Ethanimine, Methanal- and Ethanaloxime" International Journal of Molecular Sciences 4, no. 4: 231-248. https://doi.org/10.3390/i4040231