Table 3.
The atomic charges for trans o-coumaric acid as well as for lithium, sodium and potassium o-coumarates calculated in the B3LYP/6-311++G6** level.
| Atom Position | Trans o-Coumaric Acid | Li o-Coumarate | Na o-Coumarate | K o-Coumarate | ||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Mulliken | APT | NBO | Mulliken | APT | NBO | Mulliken | APT | NBO | Mulliken | APT | NBO | |
| C1 a | 1.790 | −0.230 | −0.141 | 1.920 | −0.146 | −0.131 | 1.855 | −0.074 | −0.123 | 1.855 | −0.058 | −0.121 |
| C2 | 0.148 | 0.513 | 0.353 | 0.007 | 0.481 | 0.345 | −0.110 | 0.454 | 0.340 | −0.099 | 0.450 | 0.338 |
| C3 | −0.358 | −0.115 | −0.208 | −0.296 | −0.101 | −0.282 | −0.249 | −0.088 | −0.282 | −0.272 | −0.087 | −0.283 |
| C4 | −0.278 | 0.055 | −0.165 | −0.257 | 0.026 | −0.175 | −0.271 | 0.002 | −0.183 | −0.254 | −0.002 | −0.185 |
| C5 | −0.610 | −0.212 | −0.228 | −0.673 | −0.187 | −0.230 | −0.597 | −0.166 | −0.231 | −0.602 | −0.162 | −0.231 |
| C6 | −1.334 | 0.072 | −0.144 | −1.307 | 0.046 | −0.150 | −1.350 | 0.024 | −0.155 | −1.352 | 0.019 | −0.156 |
| C7 | 0.043 | 1.575 | 0.761 | −0.446 | 1.498 | 0.735 | 0.218 | 1.418 | 0.738 | 0.295 | 1.448 | 0.743 |
| C8 | −0.239 | −0.542 | −0.307 | 0.530 | −0.449 | −0.275 | −0.162 | −0.336 | −0.262 | −0.495 | −0.338 | −0.260 |
| C9 | −0.036 | 0.370 | −0.100 | −0.010 | 0.248 | −0.130 | 0.059 | 0.134 | −0.157 | −0.039 | 0.116 | −0.160 |
| H1 (Me) | 0.292 | 0.307 | 0.481 | 0.151 | 0.843 | 0.886 | 0.557 | 0.884 | 0.918 | 0.997 | 0.957 | 0.939 |
| H2 | 0.265 | 0.294 | 0.472 | 0.260 | 0.286 | 0.469 | 0.257 | 0.280 | 0.467 | 0.256 | 0.279 | 0.466 |
| H3 | 0.126 | 0.028 | 0.203 | 0.116 | 0.022 | 0.200 | 0.117 | 0.019 | 0.197 | 0.115 | 0.017 | 0.197 |
| H4 | 0.163 | 0.041 | 0.208 | 0.161 | 0.036 | 0.205 | 0.152 | 0.032 | 0.203 | 0.151 | 0.031 | 0.203 |
| H5 | 0.182 | 0.037 | 0.209 | 0.177 | 0.032 | 0.207 | 0.171 | 0.028 | 0.204 | 0.170 | 0.027 | 0.204 |
| H6 | 0.083 | 0.049 | 0.205 | 0.085 | 0.049 | 0.205 | 0.079 | 0.049 | 0.205 | 0.077 | 0.048 | 0.205 |
| H7 | 0.209 | 0.051 | 0.208 | 0.186 | 0.037 | 0.200 | 0.171 | 0.023 | 0.192 | 0.173 | 0.024 | 0.192 |
| H8 | 0.245 | 0.086 | 0.238 | 0.264 | 0.086 | 0.237 | 0.253 | 0.084 | 0.235 | 0.252 | 0.085 | 0.235 |
| O1 | −0.185 | −0.856 | −0.691 | −0.334 | −1.121 | −0.817 | −0.463 | −1.098 | −0.813 | −0.502 | −1.141 | −0.822 |
| O2 | −0.310 | −0.871 | −0.611 | −0.339 | −1.036 | −0.827 | −0.490 | −1.019 | −0.820 | −0.527 | −1.064 | −0.830 |
| O3 | −0.195 | −0.649 | −0.67 | −0.193 | −0.649 | −0.672 | −0.198 | −0.649 | −0.674 | −0.199 | −0.648 | −0.674 |
| Sum: Ring | −0.642 | 0.083 | −0.605 | −0.606 | 0.119 | −0.623 | −0.722 | 0.152 | −0.634 | −0.724 | 0.160 | −0.638 |
| C=C | −0.275 | −0.172 | −0.407 | 0.520 | −0.201 | −0.405 | −0.103 | −0.202 | −0.419 | −0.534 | −0.222 | −0.420 |
| COO− | −0.452 | −0.152 | −0.541 | −1.119 | −0.659 | −0.909 | −0.735 | −0.699 | −0.895 | −0.734 | −0.757 | −0.909 |
a: Atom numbering.