Below, the Exchange-Scaled Functional Group Symmetry Adapted Perturbation Theory (F-sSAPT) results computed at the F-sSAPT0/jun-cc-pVDZ level for all transition states are tabulated. The columns labeled 'Frag1' and 'Frag2' contain all possible interacting fragments of Benzaldehyde and the Enamine Intermediate, respectively. Here, 'All' means the entire reactant was considered for the interaction. The 'Elst', 'Exch', and 'Disp' columns contain the computed electrostatics, exchange-repulsion, and dispersion, respectively, for the corresponding interaction interaction. 'IndAB' or 'IndBA' designate the induction of monomer A or B in the presence of the electrostatic potential of monomer B or A, respectively. Finally, the 'Total' column is the sum of the previously described energetic components. ==> RR_ENT-SYN_1 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -1.432 0.483 0.143 0.189 -0.666 -1.283 Phenyl Hex -7.935 19.329 -0.210 -1.373 -9.827 -0.017 Phenyl CarbA 4.268 0.101 -0.888 1.002 -0.435 4.048 Aldehyde Proline 2.375 4.500 2.831 -1.475 -2.595 5.635 Aldehyde Hex -33.525 52.790 -4.252 -15.017 -8.790 -8.795 Aldehyde CarbA -57.516 92.501 -72.396 -12.659 -11.423 -61.492 Phenyl All -5.099 19.913 -0.955 -0.182 -10.928 2.748 Aldehyde All -88.666 149.791 -73.817 -29.151 -22.809 -64.653 All Proline 0.943 4.983 2.973 -1.286 -3.262 4.351 All Hex -41.461 72.118 -4.462 -16.390 -18.617 -8.812 All CarbA -53.247 92.603 -73.284 -11.657 -11.858 -57.444 All All -93.765 169.704 -74.772 -29.334 -33.737 -61.904 ==> RR_ENT-SYN_2 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -1.310 0.473 0.126 0.189 -0.648 -1.170 Phenyl Hex -7.784 19.050 -0.202 -1.179 -9.829 0.056 Phenyl CarbA 4.256 0.100 -0.912 0.995 -0.437 4.002 Aldehyde Proline 2.120 4.299 2.721 -1.400 -2.561 5.179 Aldehyde Hex -32.569 50.789 -4.313 -14.016 -8.591 -8.699 Aldehyde CarbA -57.436 92.048 -71.912 -12.453 -11.372 -61.125 Phenyl All -4.838 19.622 -0.988 0.005 -10.914 2.888 Aldehyde All -87.886 147.137 -73.504 -27.868 -22.524 -64.644 All Proline 0.810 4.772 2.847 -1.211 -3.210 4.009 All Hex -40.353 69.839 -4.515 -15.194 -18.420 -8.643 All CarbA -53.180 92.148 -72.824 -11.458 -11.809 -57.122 All All -92.724 166.759 -74.491 -27.863 -33.438 -61.756 ==> RR_ENT-SYN_3 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -1.579 0.376 0.151 0.172 -0.734 -1.614 Phenyl Hex -9.279 22.101 -0.303 -2.245 -10.242 0.033 Phenyl CarbA 4.360 0.119 -0.920 1.052 -0.425 4.186 Aldehyde Proline 2.334 4.485 2.859 -1.658 -2.562 5.458 Aldehyde Hex -40.930 65.348 -4.837 -21.714 -10.160 -12.293 Aldehyde CarbA -56.997 94.178 -76.601 -13.386 -11.606 -64.412 Phenyl All -6.498 22.596 -1.071 -1.020 -11.401 2.606 Aldehyde All -95.593 164.011 -78.580 -36.757 -24.328 -71.247 All Proline 0.755 4.861 3.009 -1.485 -3.296 3.844 All Hex -50.209 87.450 -5.140 -23.959 -20.402 -12.260 All CarbA -52.637 94.297 -77.521 -12.334 -12.031 -60.225 All All -102.091 186.608 -79.651 -37.777 -35.729 -68.641 ==> RR_ENT-SYN_4 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -1.439 0.394 0.134 0.182 -0.702 -1.430 Phenyl Hex -9.135 21.764 -0.294 -2.068 -9.988 0.280 Phenyl CarbA 4.388 0.114 -0.954 1.057 -0.419 4.187 Aldehyde Proline 1.888 4.647 2.877 -1.672 -2.641 5.099 Aldehyde Hex -40.878 64.967 -5.066 -21.420 -10.100 -12.498 Aldehyde CarbA -56.774 93.158 -77.047 -13.124 -11.476 -65.264 Phenyl All -6.185 22.273 -1.113 -0.828 -11.109 3.037 Aldehyde All -95.765 162.772 -79.237 -36.216 -24.217 -72.663 All Proline 0.449 5.042 3.011 -1.490 -3.343 3.669 All Hex -50.013 86.731 -5.360 -23.488 -20.088 -12.218 All CarbA -52.386 93.272 -78.001 -12.066 -11.895 -61.077 All All -101.950 185.045 -80.350 -37.044 -35.326 -69.626 ==> RS_ENT-ANTI_1 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -0.412 0.723 0.201 0.135 -0.717 -0.069 Phenyl Hex -10.105 19.998 -0.345 -2.353 -7.948 -0.752 Phenyl CarbA -0.028 3.868 -1.019 0.106 -1.861 1.067 Aldehyde Proline 1.207 4.272 1.701 -1.723 -2.542 2.916 Aldehyde Hex -41.812 69.902 -4.825 -22.647 -11.511 -10.894 Aldehyde CarbA -39.228 64.612 -35.402 -5.789 -8.078 -23.885 Phenyl All -10.545 24.590 -1.163 -2.112 -10.525 0.245 Aldehyde All -79.833 138.786 -38.526 -30.159 -22.131 -31.863 All Proline 0.796 4.996 1.902 -1.588 -3.258 2.847 All Hex -51.917 89.900 -5.171 -25.000 -19.458 -11.647 All CarbA -39.257 68.481 -36.420 -5.682 -9.939 -22.818 All All -90.378 163.376 -39.689 -32.271 -32.656 -31.617 ==> RS_ENT-ANTI_2 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -0.316 0.759 0.162 0.098 -0.740 -0.038 Phenyl Hex -10.644 20.787 -0.454 -2.747 -7.985 -1.043 Phenyl CarbA -0.087 3.552 -0.804 0.093 -1.748 1.006 Aldehyde Proline 0.588 4.095 1.404 -1.767 -2.468 1.853 Aldehyde Hex -45.436 76.670 -5.026 -25.159 -12.369 -11.321 Aldehyde CarbA -36.121 58.055 -28.349 -4.654 -7.289 -18.358 Phenyl All -11.047 25.098 -1.096 -2.556 -10.473 -0.075 Aldehyde All -80.969 138.820 -31.971 -31.580 -22.125 -27.826 All Proline 0.272 4.854 1.565 -1.669 -3.208 1.814 All Hex -56.080 97.457 -5.480 -27.906 -20.354 -12.364 All CarbA -36.208 61.607 -29.152 -4.561 -9.037 -17.352 All All -92.017 163.918 -33.067 -34.137 -32.599 -27.901 ==> RS_ENT-ANTI_3 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -0.310 0.601 0.256 0.184 -0.703 0.028 Phenyl Hex -7.974 17.395 -0.079 -1.253 -7.208 0.881 Phenyl CarbA -0.174 4.471 -1.459 0.091 -2.079 0.850 Aldehyde Proline 2.166 3.884 2.350 -1.377 -2.437 4.586 Aldehyde Hex -33.835 54.575 -4.266 -15.651 -9.693 -8.869 Aldehyde CarbA -44.884 77.270 -52.091 -8.407 -9.697 -37.808 Phenyl All -8.457 22.466 -1.282 -0.977 -9.990 1.760 Aldehyde All -76.552 135.729 -54.007 -25.434 -21.827 -42.091 All Proline 1.856 4.484 2.606 -1.192 -3.140 4.614 All Hex -41.808 71.970 -4.345 -16.904 -16.901 -7.988 All CarbA -45.057 81.741 -53.550 -8.316 -11.776 -36.958 All All -85.010 158.195 -55.289 -26.411 -31.817 -40.332 ==> RS_ENT-ANTI_4 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -0.228 0.639 0.222 0.178 -0.741 0.070 Phenyl Hex -8.713 18.340 -0.185 -1.669 -7.317 0.455 Phenyl CarbA -0.142 4.018 -1.223 0.081 -1.916 0.819 Aldehyde Proline 1.414 4.151 2.181 -1.518 -2.559 3.668 Aldehyde Hex -37.425 61.377 -4.659 -18.717 -10.532 -9.956 Aldehyde CarbA -42.438 72.399 -45.880 -7.327 -9.015 -32.261 Phenyl All -9.083 22.996 -1.186 -1.410 -9.974 1.344 Aldehyde All -78.449 137.927 -48.358 -27.563 -22.106 -38.549 All Proline 1.186 4.789 2.403 -1.340 -3.300 3.739 All Hex -46.138 79.717 -4.845 -20.387 -17.849 -9.501 All CarbA -42.580 76.417 -47.103 -7.246 -10.931 -31.443 All All -87.531 160.923 -49.545 -28.973 -32.080 -37.205 ==> SR_ANTI_1 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -0.833 0.805 0.110 0.280 -1.013 -0.651 Phenyl Hex -8.153 17.186 -0.352 -1.440 -7.230 0.010 Phenyl CarbA 3.864 0.102 -0.623 0.814 -0.340 3.818 Aldehyde Proline 1.003 6.293 2.275 -1.893 -3.358 4.319 Aldehyde Hex -32.414 51.401 -4.387 -14.413 -8.980 -8.793 Aldehyde CarbA -49.936 75.987 -50.602 -8.299 -9.082 -41.931 Phenyl All -5.122 18.092 -0.865 -0.346 -8.583 3.176 Aldehyde All -81.347 133.682 -52.714 -24.605 -21.420 -46.404 All Proline 0.171 7.098 2.384 -1.613 -4.371 3.668 All Hex -40.568 68.587 -4.739 -15.854 -16.210 -8.783 All CarbA -46.072 76.089 -51.225 -7.485 -9.421 -38.113 All All -86.469 151.774 -53.579 -24.952 -30.002 -43.228 ==> SR_ANTI_2 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -0.822 0.931 0.083 0.287 -1.128 -0.649 Phenyl Hex -8.020 16.997 -0.315 -1.453 -7.247 -0.037 Phenyl CarbA 3.846 0.112 -0.662 0.812 -0.334 3.774 Aldehyde Proline 0.382 7.057 2.289 -1.957 -3.653 4.118 Aldehyde Hex -32.610 51.166 -4.556 -14.277 -8.947 -9.224 Aldehyde CarbA -49.354 75.607 -50.995 -8.184 -9.032 -41.957 Phenyl All -4.996 18.040 -0.894 -0.353 -8.709 3.089 Aldehyde All -81.582 133.829 -53.261 -24.417 -21.633 -47.063 All Proline -0.440 7.988 2.372 -1.669 -4.781 3.469 All Hex -40.630 68.163 -4.871 -15.730 -16.194 -9.261 All CarbA -45.507 75.719 -51.657 -7.371 -9.367 -38.182 All All -86.578 151.870 -54.155 -24.770 -30.342 -43.975 ==> SR_ANTI_3 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -0.841 0.614 0.139 0.278 -0.875 -0.685 Phenyl Hex -7.545 16.667 -0.268 -1.126 -7.010 0.718 Phenyl CarbA 4.215 0.104 -0.796 0.935 -0.372 4.085 Aldehyde Proline 1.680 5.688 2.756 -1.745 -3.181 5.199 Aldehyde Hex -30.615 48.300 -4.340 -12.750 -8.466 -7.869 Aldehyde CarbA -53.534 83.366 -63.377 -10.019 -10.076 -53.639 Phenyl All -4.172 17.384 -0.925 0.088 -8.257 4.118 Aldehyde All -82.468 137.354 -64.960 -24.514 -21.722 -56.310 All Proline 0.839 6.302 2.896 -1.467 -4.056 4.514 All Hex -38.160 64.967 -4.608 -13.875 -15.476 -7.152 All CarbA -49.319 83.469 -64.173 -9.083 -10.448 -49.554 All All -86.640 154.739 -65.885 -24.426 -29.979 -52.192 ==> SR_ANTI_4 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -0.780 0.728 0.113 0.285 -0.985 -0.639 Phenyl Hex -7.453 16.515 -0.239 -1.157 -7.001 0.665 Phenyl CarbA 4.192 0.115 -0.831 0.933 -0.364 4.045 Aldehyde Proline 0.905 6.427 2.688 -1.777 -3.432 4.811 Aldehyde Hex -31.118 48.535 -4.536 -12.828 -8.478 -8.426 Aldehyde CarbA -52.744 82.734 -63.705 -9.836 -10.001 -53.552 Phenyl All -4.041 17.358 -0.958 0.062 -8.350 4.071 Aldehyde All -82.957 137.696 -65.553 -24.441 -21.911 -57.167 All Proline 0.125 7.155 2.801 -1.492 -4.417 4.172 All Hex -38.571 65.050 -4.776 -13.985 -15.479 -7.761 All CarbA -48.552 82.849 -64.536 -8.903 -10.365 -49.507 All All -86.998 155.054 -66.511 -24.380 -30.261 -53.096 ==> SS_SYN_1 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -1.271 0.528 0.211 0.292 -0.804 -1.043 Phenyl Hex -7.413 19.767 0.039 -1.156 -10.036 1.201 Phenyl CarbA -0.219 4.231 -1.402 0.035 -1.927 0.720 Aldehyde Proline 1.290 7.173 2.695 -1.931 -3.562 5.665 Aldehyde Hex -31.110 45.993 -4.657 -12.516 -8.009 -10.299 Aldehyde CarbA -48.396 78.876 -59.814 -9.188 -9.824 -48.345 Phenyl All -8.902 24.527 -1.152 -0.829 -12.767 0.878 Aldehyde All -78.216 132.043 -61.776 -23.634 -21.394 -52.978 All Proline 0.019 7.701 2.906 -1.638 -4.366 4.622 All Hex -38.522 65.761 -4.619 -13.672 -18.045 -9.098 All CarbA -48.614 83.108 -61.216 -9.152 -11.750 -47.625 All All -87.118 156.570 -62.929 -24.463 -34.161 -52.100 ==> SS_SYN_2 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -1.147 0.499 0.194 0.303 -0.852 -1.003 Phenyl Hex -7.638 20.120 0.023 -1.247 -10.133 1.125 Phenyl CarbA -0.040 3.806 -1.360 0.066 -1.834 0.639 Aldehyde Proline 0.390 8.138 2.750 -2.025 -3.910 5.342 Aldehyde Hex -31.647 46.478 -4.882 -12.867 -8.073 -10.991 Aldehyde CarbA -47.396 77.750 -58.950 -8.876 -9.672 -47.144 Phenyl All -8.825 24.426 -1.144 -0.877 -12.819 0.761 Aldehyde All -78.654 132.366 -61.081 -23.769 -21.656 -52.794 All Proline -0.757 8.637 2.944 -1.722 -4.762 4.339 All Hex -39.286 66.599 -4.859 -14.114 -18.206 -9.866 All CarbA -47.436 81.556 -60.310 -8.810 -11.506 -46.505 All All -87.479 156.792 -62.225 -24.646 -34.474 -52.033 ==> SS_SYN_3 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -1.255 0.360 0.257 0.279 -0.844 -1.203 Phenyl Hex -7.288 20.262 0.139 -1.153 -9.929 2.032 Phenyl CarbA -0.789 5.503 -1.730 -0.081 -2.196 0.707 Aldehyde Proline 1.917 6.491 3.171 -1.795 -3.346 6.437 Aldehyde Hex -31.696 46.854 -4.822 -12.666 -8.032 -10.363 Aldehyde CarbA -51.241 84.534 -71.865 -10.728 -10.635 -59.936 Phenyl All -9.332 26.126 -1.334 -0.955 -12.969 1.536 Aldehyde All -81.020 137.878 -73.517 -25.190 -22.013 -63.862 All Proline 0.661 6.850 3.428 -1.516 -4.190 5.234 All Hex -38.983 67.116 -4.683 -13.820 -17.961 -8.331 All CarbA -52.030 90.037 -73.595 -10.809 -12.831 -59.228 All All -90.352 164.004 -74.851 -26.145 -34.981 -62.325 ==> SS_SYN_4 <== Frag1 Frag2 Elst Exch IndAB IndBA Disp Total Phenyl Proline -1.179 0.319 0.238 0.294 -0.910 -1.237 Phenyl Hex -7.573 20.744 0.125 -1.236 -10.182 1.879 Phenyl CarbA -0.523 4.964 -1.689 -0.027 -2.096 0.628 Aldehyde Proline 0.924 7.420 3.127 -1.831 -3.612 6.028 Aldehyde Hex -32.126 47.130 -5.015 -12.897 -8.057 -10.965 Aldehyde CarbA -50.302 83.779 -71.624 -10.444 -10.541 -59.132 Phenyl All -9.275 26.027 -1.326 -0.969 -13.187 1.270 Aldehyde All -81.504 138.329 -73.512 -25.172 -22.210 -64.069 All Proline -0.255 7.738 3.365 -1.536 -4.521 4.791 All Hex -39.698 67.874 -4.890 -14.133 -18.239 -9.086 All CarbA -50.825 88.743 -73.313 -10.472 -12.637 -58.504 All All -90.779 164.356 -74.838 -26.141 -35.397 -62.799