Supporting information A Nonradical Zinc-Barbier Reaction for Diastereoselective Synthesis of Vicinal Amino Alcohols Lise Keinicke, Peter Fristrup, Per-Ola Norrby,* and Robert Madsen* Center for Sustainable and Green Chemistry, Department of Chemistry, Technical University of Denmark, Building 201, DK-2800 Kgs. Lyngby, Denmark For questions regarding the computational results, contact Per-Ola Norrby, pon@kemi.dtu.dk. Transition states at B3LYP/LACVP*, converged on gradients. For gas phase calculations, potential energy and vibrational free energy corrections at 298 K. For solvated calculations, free energy in solvent, but not including vibrational corrections. Br_HCO_2Me_chair_Z_Prox_TS_freq E_scf = -557.92560337554 a.u. G(T)-E(0) = 0.143671 a.u. Lowest frequency: -321.51 cm-1 Zn 0.00000 0.00000 0.00000 Br 0.00000 0.00000 2.42699 C 2.09904 0.00000 -1.02427 C 1.60421 0.47878 -2.22460 C 0.64377 -0.04460 -3.12717 C -1.11034 0.91416 -2.52202 N -1.50774 0.48328 -1.31481 H 2.79147 0.62664 -0.46927 H 2.17083 -1.06300 -0.81602 H 1.83038 1.52040 -2.45014 H 0.69758 0.31296 -4.15004 H -1.70125 0.56400 -3.37854 C 0.17546 -2.28685 -2.23040 O 0.43051 -1.46328 -3.22686 O -0.01937 -2.03163 -1.04775 H 0.14873 -3.31562 -2.60903 C -2.60880 -0.48500 -1.26373 H -3.01493 -0.69425 -2.26438 H -2.31100 -1.43979 -0.81290 H -3.41974 -0.07361 -0.64955 C -0.68450 2.36495 -2.64349 H -0.08598 2.68099 -1.78348 H -0.12999 2.56810 -3.56611 H -1.59077 2.98370 -2.64750 Br_HCO_2Me_chair_Z_Dist_TS_freq E_scf = -557.93286173216 a.u. G(T)-E(0) = 0.142101 a.u. Lowest frequency: -366.88 cm-1 Zn 0.00000 0.00000 0.00000 Br 0.00000 0.00000 2.41664 C 1.84876 0.00000 -1.28103 C 1.43736 0.92970 -2.24083 C 0.54428 0.68596 -3.29682 C -1.27298 0.89217 -2.39304 N -1.42856 -0.03389 -1.42864 H 2.61354 0.30289 -0.56840 H 1.86983 -1.05332 -1.56052 H 1.65539 1.98176 -2.06023 H 0.46254 1.39399 -4.11439 H -1.79389 0.69788 -3.33563 C -0.08298 -0.91973 -4.91178 O 0.50249 -0.66576 -3.72546 O -0.60702 -0.10636 -5.63300 H -0.00482 -1.99621 -5.12091 C -1.95272 -1.35176 -1.80825 H -2.60957 -1.27508 -2.68453 H -1.16519 -2.07909 -2.04500 H -2.54485 -1.75253 -0.97752 C -1.29126 2.34552 -1.96270 H -0.67927 2.51334 -1.06717 H -0.93385 3.01120 -2.75448 H -2.31802 2.63241 -1.70520 Br_HCO_2Me_chair_E_Prox_TS_freq E_scf = -557.92651523004 a.u. G(T)-E(0) = 0.141600 a.u. Lowest frequency: -356.60 cm-1 Zn 0.00000 0.00000 0.00000 C 0.00000 0.00000 2.23478 C 1.36552 0.00000 2.55488 C 2.17581 -1.14522 2.42365 C 2.47922 -1.30110 0.39742 N 1.31270 -1.52715 -0.23040 H -0.56465 0.90330 2.45872 H -0.56469 -0.92506 2.36964 H 1.85625 0.94792 2.74757 H 1.69558 -2.11460 2.52653 H 3.12434 -2.17020 0.56309 C 4.24701 -0.25638 3.37619 O 3.46677 -1.28183 2.99623 O 4.01477 0.92534 3.28169 H 5.17078 -0.67748 3.80026 Br -1.34522 1.36012 -1.47151 C 0.78977 -2.89264 -0.16520 H 1.56014 -3.62061 -0.45204 H 0.43025 -3.17022 0.83998 H -0.04780 -2.99831 -0.86200 C 3.21779 -0.03508 0.01442 H 2.54422 0.83173 -0.02142 H 4.02900 0.20479 0.70367 H 3.63585 -0.15670 -0.99229 Br_HCO_2Me_chair_E_Dist_TS_freq E_scf = -557.93345618827 a.u. G(T)-E(0) = 0.141653 a.u. Lowest frequency: -361.79 cm-1 Zn 0.00000 0.00000 0.00000 C 0.00000 0.00000 2.24206 C 1.36564 0.00000 2.55053 C 2.21500 -1.11132 2.42522 C 2.47188 -1.31490 0.40866 N 1.29724 -1.53613 -0.20835 H -0.56937 0.89707 2.47749 H -0.55700 -0.93059 2.36744 H 1.85145 0.95801 2.73861 H 1.84134 -2.11469 2.60396 H 3.10400 -2.19220 0.57401 C 4.28542 -1.98941 3.15226 O 3.51249 -0.90378 2.95832 O 3.98375 -3.13055 2.89814 H 5.24283 -1.66688 3.58547 Br -1.29872 1.41039 -1.46592 C 0.76470 -2.89815 -0.12043 H 1.52999 -3.63510 -0.39537 H 0.40721 -3.15601 0.89021 H -0.07472 -3.00895 -0.81432 C 3.22297 -0.05798 0.02027 H 2.55439 0.81186 -0.04189 H 4.02059 0.17554 0.72971 H 3.66463 -0.19140 -0.97440 Br_HCO_2Me_boat_Z_Prox_TS_freq E_scf = -557.93324233189 a.u. G(T)-E(0) = 0.144000 a.u. Lowest frequency: -293.60 cm-1 Zn 0.00000 0.00000 0.00000 Br 0.00000 0.00000 2.42583 C 2.16302 0.00000 -1.07399 C 1.67434 0.34376 -2.31484 C 0.73978 -0.32336 -3.14618 C -1.10984 0.61309 -2.59093 N -1.05394 1.10520 -1.34124 H 2.83316 0.68668 -0.56546 H 2.23458 -1.03638 -0.75422 H 1.84823 1.36872 -2.64528 H 0.76018 -0.09323 -4.20603 H -1.03771 1.35147 -3.39868 C 0.25751 -2.41111 -1.99121 O 0.63906 -1.76107 -3.06379 O -0.09910 -1.95063 -0.90869 H 0.28388 -3.49106 -2.17209 C -0.70072 2.52769 -1.24553 H -1.41586 3.14516 -1.80546 H -0.73801 2.84219 -0.19782 H 0.30711 2.75424 -1.63173 C -2.09511 -0.49575 -2.89588 H -2.17505 -1.20878 -2.07305 H -3.08375 -0.03401 -3.01933 H -1.85482 -1.02667 -3.82199 Br_HCO_2Me_boat_Z_Dist_TS_freq E_scf = -557.92301928298 a.u. G(T)-E(0) = 0.142138 a.u. Lowest frequency: -348.39 cm-1 Zn 0.00000 0.00000 0.00000 Br 0.00000 0.00000 2.41228 C 1.96554 0.00000 -1.18810 C 1.47116 -0.17802 -2.47299 C 0.79898 -1.33551 -2.92831 C -1.16577 -0.93887 -2.46363 N -1.32667 0.01724 -1.51148 H 2.47318 0.92976 -0.94217 H 2.30672 -0.87566 -0.63455 H 1.37996 0.69264 -3.12131 H 0.72514 -1.54139 -3.99047 H -1.43980 -0.62763 -3.47732 C 1.19341 -3.67799 -2.80027 O 1.13743 -2.48639 -2.16683 O 0.95248 -3.87527 -3.96462 H 1.49317 -4.44604 -2.07332 C -1.45378 1.38317 -2.03271 H -2.27852 1.44514 -2.75527 H -1.68148 2.07310 -1.21238 H -0.54460 1.74782 -2.54244 C -1.65822 -2.32748 -2.10716 H -1.25108 -2.67245 -1.15067 H -2.74852 -2.28183 -2.00244 H -1.41616 -3.05951 -2.88134 Br_HCO_2Me_boat_E_Prox_TS_freq E_scf = -557.92318489557 a.u. G(T)-E(0) = 0.142008 a.u. Lowest frequency: -345.74 cm-1 Zn 0.00000 0.00000 0.00000 C 0.00000 0.00000 2.28014 C 1.35830 0.00000 2.57833 C 2.18404 -1.14829 2.46081 C 2.33156 -1.57316 0.47249 N 1.87602 -0.61821 -0.36688 H -0.57480 0.90137 2.48217 H -0.56827 -0.92892 2.36776 H 1.84937 0.95816 2.71719 H 1.73860 -2.09446 2.75102 H 3.42137 -1.66574 0.53688 C 4.35114 -0.13385 2.89426 O 3.50308 -1.16777 2.99833 O 4.12867 0.95632 2.42001 H 5.31470 -0.43645 3.32987 Br -1.97689 0.57146 -1.25951 C 2.79232 0.50363 -0.60427 H 3.76764 0.13518 -0.95066 H 2.38405 1.15059 -1.38776 H 2.97632 1.10257 0.30064 C 1.59005 -2.89735 0.41462 H 0.51859 -2.76960 0.62469 H 1.67367 -3.31694 -0.59401 H 1.99057 -3.62173 1.12969 Br_HCO_2Me_boat_E_Dist_TS_freq E_scf = -557.92793964790 a.u. G(T)-E(0) = 0.141692 a.u. Lowest frequency: -358.76 cm-1 Zn 0.00000 0.00000 0.00000 C 0.00000 0.00000 2.27060 C 1.35587 0.00000 2.59182 C 2.21676 -1.11167 2.47407 C 2.36175 -1.52756 0.47939 N 1.91193 -0.54503 -0.33044 H -0.58356 0.88961 2.49791 H -0.55825 -0.93552 2.35098 H 1.83975 0.96187 2.76725 H 1.86530 -2.09331 2.77437 H 3.45066 -1.60774 0.55853 C 4.31925 -1.90013 3.20036 O 3.53082 -0.84131 2.94411 O 4.02116 -3.06173 3.05191 H 5.28825 -1.53790 3.57208 Br -1.95222 0.54065 -1.30919 C 2.79601 0.61637 -0.43103 H 3.82270 0.30979 -0.67204 H 2.44662 1.28447 -1.22505 H 2.84213 1.19138 0.51209 C 1.63303 -2.85412 0.39812 H 0.56264 -2.74470 0.62457 H 1.70952 -3.25038 -0.62075 H 2.06013 -3.57887 1.09531 2Me_HCO_solv_chair_Z_Prox_TS Gradients converged E_sol = -544.56843325677 a.u. Zn -0.00632 0.43938 -0.09174 C -0.18164 -0.21938 2.06548 C 1.18928 -0.14894 2.32269 C 2.24959 -1.02331 2.00697 C 2.82365 -0.30099 0.16614 N 1.84168 -0.17205 -0.76400 H -0.79705 0.56753 2.50053 H -0.67493 -1.17481 1.91872 H 1.55736 0.81588 2.67157 H 3.18239 -0.82270 2.51945 H 3.49267 -1.15504 0.00734 C 1.23343 -3.15140 1.33456 O 2.13233 -2.44097 2.01605 O 0.43025 -2.72125 0.53172 H 1.34207 -4.21134 1.60304 C 1.77489 -1.26406 -1.75635 H 2.77128 -1.45463 -2.17028 H 1.38239 -2.19959 -1.34791 H 1.13180 -0.95811 -2.58781 C 3.55839 0.95357 0.60844 H 2.87615 1.74507 0.93196 H 4.26590 0.74828 1.41901 H 4.12927 1.34164 -0.24518 2Me_HCO_solv_chair_Z_Dist_TS Gradients converged E_sol = -544.58082513127 a.u. Zn -0.00643 -0.05019 0.01994 C 0.01499 0.03522 2.28331 C 1.39346 0.03858 2.51855 C 2.23608 -1.08173 2.43166 C 2.68562 -1.10866 0.48737 N 1.59805 -1.33599 -0.29161 H -0.53708 0.95006 2.49523 H -0.53310 -0.89008 2.46317 H 1.90589 0.99514 2.60211 H 3.22579 -1.04407 2.87475 H 3.32730 -1.98338 0.63408 C 2.33352 -3.39427 2.93469 O 1.57867 -2.32286 2.62904 O 3.54082 -3.39911 3.02054 H 1.68518 -4.26419 3.09969 C 1.23581 -2.75583 -0.47269 H 2.13309 -3.38691 -0.46549 H 0.55692 -3.13308 0.30070 H 0.74785 -2.89131 -1.44383 C 3.46900 0.17080 0.27609 H 2.82075 1.05205 0.26808 H 4.22504 0.30750 1.05536 H 3.98228 0.12540 -0.69252 2Me_HCO_solv_chair_E_Prox_TS Gradients converged E_sol = -544.57476649562 a.u. Zn 0.00348 -0.00170 -0.00225 C -0.00275 -0.00366 2.25308 C 1.34418 0.00023 2.64988 C 2.15463 -1.14598 2.52080 C 2.59481 -1.17648 0.57574 N 1.49818 -1.44312 -0.17407 H -0.58707 0.88274 2.49924 H -0.55327 -0.94431 2.33102 H 1.80986 0.94139 2.91813 H 1.65973 -2.11279 2.55816 H 3.25332 -2.03354 0.75063 C 4.16294 -0.35478 3.69422 O 3.40484 -1.32869 3.16816 O 3.93076 0.83365 3.69043 H 5.05539 -0.81593 4.13939 C 1.06343 -2.84754 -0.09592 H 1.90944 -3.52165 -0.28228 H 0.64430 -3.11229 0.88759 H 0.29997 -3.05293 -0.85093 C 3.33559 0.11530 0.30201 H 2.66068 0.97731 0.32909 H 4.13375 0.29227 1.02580 H 3.78556 0.07288 -0.69726 2Me_HCO_solv_chair_E_Dist_TS Gradients converged E_sol = -544.58099680163 a.u. Zn 0.02886 0.00483 -0.02315 C -0.01925 -0.02760 2.24632 C 1.32369 -0.01524 2.64244 C 2.17997 -1.12738 2.56461 C 2.56343 -1.29583 0.60382 N 1.44191 -1.51567 -0.12364 H -0.61294 0.85297 2.49029 H -0.56429 -0.97267 2.30036 H 1.78433 0.93976 2.89477 H 1.79421 -2.12990 2.72534 H 3.15494 -2.19316 0.80804 C 4.22350 -1.97824 3.42333 O 3.43671 -0.91318 3.18753 O 3.96157 -3.12372 3.13002 H 5.14133 -1.64726 3.92606 C 0.90368 -2.87862 0.02670 H 1.69069 -3.62418 -0.14213 H 0.48554 -3.06263 1.02854 H 0.11136 -3.05699 -0.70514 C 3.39410 -0.07282 0.28320 H 2.77835 0.83270 0.24738 H 4.18169 0.08082 1.02492 H 3.86796 -0.19590 -0.69846 2Me_HCO_solv_boat_Z_Prox_TS Gradients converged E_sol = -544.57767705127 a.u. Zn 0.01695 -0.00018 -0.02270 C -0.00018 -0.01102 2.35703 C 1.37671 0.01631 2.50490 C 2.34155 -0.91482 2.05842 C 2.90253 -0.14030 0.20753 N 1.94585 0.64125 -0.35789 H -0.57077 0.82689 2.75103 H -0.54059 -0.95500 2.31522 H 1.82955 0.95203 2.83141 H 3.31256 -0.90281 2.54165 H 3.73362 0.41464 0.65340 C 1.05239 -2.75928 1.12528 O 1.97363 -2.30098 1.93799 O 0.39904 -2.11462 0.30080 H 0.92590 -3.83912 1.25211 C 3.37481 -1.38922 -0.51149 H 2.55695 -1.98141 -0.92701 H 4.00730 -1.06651 -1.34908 H 3.98572 -2.02314 0.13855 C 2.09308 2.06708 -0.01037 H 3.10084 2.42147 -0.26157 H 1.37784 2.66552 -0.58210 H 1.92854 2.27323 1.05848 2Me_HCO_solv_boat_Z_Dist_TS Gradients converged E_sol = -544.56729913337 a.u. Zn -0.02811 -0.11018 0.10313 C 0.19833 0.38199 2.35827 C 1.56629 0.20734 2.53218 C 2.22112 -1.04855 2.52433 C 2.62888 -1.35011 0.57227 N 1.95779 -0.54099 -0.30545 H -0.20508 1.39090 2.42677 H -0.46779 -0.41456 2.68538 H 2.22280 1.07311 2.47335 H 3.21627 -1.11596 2.96039 H 3.68468 -1.08609 0.67993 C 1.85258 -3.09025 3.69307 O 1.36978 -2.11746 2.89558 O 1.16660 -4.02452 4.02478 H 2.89934 -2.94331 4.00334 C 2.41493 -2.84513 0.43989 H 1.37219 -3.13681 0.57549 H 2.72743 -3.14955 -0.56580 H 3.01936 -3.40510 1.15928 C 2.66519 0.73497 -0.52160 H 3.70345 0.54418 -0.82220 H 2.19015 1.30971 -1.32131 H 2.70119 1.37202 0.37755 2Me_HCO_solv_boat_E_Dist_TS Gradients converged E_sol = -544.57611412135 a.u. Zn 0.00221 -0.00375 -0.00297 C -0.00892 -0.00529 2.28389 C 1.35234 -0.00415 2.59464 C 2.18053 -1.14700 2.56468 C 2.23608 -1.77150 0.66001 N 1.89016 -0.83691 -0.26376 H -0.57128 0.90299 2.49558 H -0.57240 -0.93254 2.40335 H 1.85405 0.95733 2.71149 H 3.31542 -1.93287 0.74027 H 1.81650 -2.08123 2.98076 C 1.41808 -3.04495 0.72327 H 0.37974 -2.84624 1.01596 H 1.40476 -3.53058 -0.25985 H 1.84861 -3.73862 1.45042 C 2.90845 0.21531 -0.39067 H 3.90769 -0.22304 -0.51259 H 2.70688 0.84424 -1.26208 H 2.94615 0.86413 0.50221 C 4.31719 -1.88361 3.27821 O 3.51415 -0.85282 2.96573 O 4.00371 -3.05374 3.23421 H 5.30218 -1.50258 3.57837 2Me_HCO_solv_boat_E_Prox_TS Gradients converged E_sol = -544.57086327021 a.u. Zn 0.00805 -0.00172 0.00508 C -0.00427 0.00036 2.29303 C 1.35841 0.00148 2.58427 C 2.14526 -1.17992 2.54244 C 2.24586 -1.77070 0.64649 N 1.85444 -0.87964 -0.30715 H -0.56165 0.91589 2.48590 H -0.57032 -0.92473 2.41511 H 1.86259 0.95742 2.68715 H 3.33193 -1.89804 0.71213 H 1.66921 -2.07851 2.92175 C 1.47719 -3.07818 0.71580 H 0.42352 -2.91394 0.97178 H 1.51300 -3.58187 -0.25692 H 1.90687 -3.74775 1.46679 C 2.88108 0.13437 -0.60344 H 3.83869 -0.35150 -0.83449 H 2.58964 0.72325 -1.47792 H 3.06114 0.81465 0.24137 C 4.37228 -0.23544 2.88127 O 3.46815 -1.20686 3.07328 O 4.19089 0.82768 2.32748 H 5.32834 -0.55441 3.31857 2Ph_HCO_solv_chair_Z_Prox_TS Gradients converged E_sol = -928.03866822448 a.u. Zn -0.00572 -0.00046 0.00742 C 0.00893 0.00463 2.26892 C 1.40253 0.00069 2.32248 C 2.33939 -0.98407 1.95153 C 2.94978 -0.27584 0.07497 N 1.91181 -0.28476 -0.81931 H -0.49732 0.89621 2.63309 H -0.55567 -0.92019 2.36098 H 1.88782 0.95385 2.52721 H 3.32109 -0.91754 2.40485 H 3.64687 -1.11393 -0.02182 C 0.99329 -2.89154 1.22792 O 2.01884 -2.36582 1.88301 O 0.20560 -2.30702 0.49684 H 0.94533 -3.96842 1.42144 C 2.32881 -2.98814 -4.08050 C 3.43611 -2.29893 -3.57616 C 3.29735 -1.42196 -2.49980 C 2.04118 -1.21898 -1.88184 C 0.93521 -1.90821 -2.41231 C 1.07681 -2.77894 -3.49409 H 2.43723 -3.66872 -4.92111 H 4.41526 -2.42723 -4.03304 H 4.15968 -0.85282 -2.16338 H -0.04533 -1.79052 -1.95911 H 0.20373 -3.30703 -3.87065 C 5.00139 3.36676 1.11217 C 3.81720 3.42125 0.37089 C 3.14489 2.24318 0.03986 C 3.63073 0.99612 0.45888 C 4.83397 0.95070 1.18820 C 5.51413 2.12586 1.50959 H 5.53066 4.28232 1.36463 H 3.42639 4.37833 0.03359 H 2.25978 2.27592 -0.58291 H 5.25162 -0.00919 1.48770 H 6.44807 2.07438 2.06377 2Ph_HCO_solv_chair_Z_Dist_TS Gradients converged E_sol = -928.04407169832 a.u. Zn -0.00354 -0.02862 -0.00658 C -0.01397 0.00223 2.27547 C 1.36305 0.02444 2.48382 C 2.21545 -1.09958 2.41540 C 2.71565 -1.17136 0.50733 N 1.59718 -1.30968 -0.27845 H -0.57738 0.91324 2.47430 H -0.55326 -0.93040 2.44101 H 1.87307 0.98406 2.54113 H 3.19572 -1.03942 2.87600 H 3.25113 -2.11171 0.66210 C 2.33818 -3.41164 2.86373 O 1.56216 -2.33072 2.64476 O 3.54724 -3.41230 2.83815 H 1.70581 -4.28363 3.07035 C 5.53216 2.06419 0.05022 C 4.28429 2.14642 -0.57307 C 3.36505 1.10232 -0.43554 C 3.66297 -0.02344 0.34074 C 4.92568 -0.09946 0.95681 C 5.85273 0.93243 0.81017 H 6.25464 2.86863 -0.06387 H 4.03098 3.01294 -1.17913 H 2.41430 1.15379 -0.95392 H 5.18713 -0.98155 1.53870 H 6.82857 0.85196 1.28252 C 0.63665 -5.29471 -1.41989 C 1.81540 -4.68340 -1.86325 C 2.12883 -3.38127 -1.46977 C 1.26773 -2.66351 -0.61668 C 0.09668 -3.29141 -0.16472 C -0.22123 -4.59188 -0.56809 H 0.39273 -6.30741 -1.73120 H 2.49033 -5.21606 -2.53024 H 3.03131 -2.89980 -1.83966 H -0.54256 -2.77634 0.54863 H -1.13047 -5.06093 -0.19788 2Ph_HCO_solv_chair_E_Prox_TS Gradients converged E_sol = -928.03735266908 a.u. Zn -0.01689 0.00745 -0.00837 C -0.01588 0.03196 2.25394 C 1.33727 0.03639 2.61108 C 2.18579 -1.08279 2.50252 C 2.70443 -1.11560 0.58390 N 1.59859 -1.29189 -0.20497 H -0.58881 0.93024 2.48377 H -0.57244 -0.90038 2.35550 H 1.81340 0.98756 2.84781 H 1.75959 -2.08206 2.56442 H 3.26831 -2.03656 0.75651 C 3.54874 -1.30072 4.42946 O 3.45931 -0.98775 3.12011 O 2.62843 -1.63566 5.13545 H 4.59528 -1.20524 4.74896 C 0.60669 -5.36867 -0.91989 C 1.76091 -4.80064 -1.47212 C 2.08292 -3.46641 -1.22054 C 1.25252 -2.67026 -0.40818 C 0.10871 -3.25490 0.15659 C -0.21696 -4.59069 -0.10377 H 0.35674 -6.40729 -1.11987 H 2.41120 -5.39536 -2.10928 H 2.96884 -3.02167 -1.66754 H -0.51140 -2.67458 0.83407 H -1.10602 -5.02344 0.34884 C 5.41173 2.21538 0.13356 C 4.07245 2.36358 -0.24230 C 3.18975 1.28936 -0.11467 C 3.61473 0.05962 0.40556 C 4.96619 -0.07844 0.76884 C 5.85712 0.98730 0.63175 H 6.10414 3.04719 0.02911 H 3.71946 3.31075 -0.64206 H 2.16342 1.40407 -0.44881 H 5.31880 -1.02797 1.16135 H 6.89922 0.85794 0.91421 2Ph_HCO_solv_chair_E_Dist_TS Gradients converged E_sol = -928.04030919383 a.u. Zn 0.02287 0.01400 -0.01984 C -0.05836 -0.02214 2.24256 C 1.28127 0.00186 2.65622 C 2.16266 -1.09567 2.60499 C 2.62846 -1.30128 0.66116 N 1.50738 -1.44573 -0.10679 H -0.65574 0.85897 2.47745 H -0.60119 -0.96458 2.31485 H 1.72134 0.95808 2.93534 H 1.78817 -2.10670 2.73838 H 3.11442 -2.25250 0.88547 C 4.24605 -1.87542 3.42332 O 3.38337 -0.85317 3.27514 O 4.07437 -3.00098 3.01197 H 5.12562 -1.52975 3.98093 C 0.24767 -5.48571 -0.57791 C 1.47208 -5.04770 -1.09580 C 1.87832 -3.72396 -0.92735 C 1.06571 -2.80716 -0.23221 C -0.15534 -3.25824 0.29159 C -0.56333 -4.58492 0.11549 H -0.06708 -6.51753 -0.71047 H 2.11216 -5.73638 -1.64200 H 2.81817 -3.38321 -1.35426 H -0.77592 -2.58210 0.87207 H -1.50887 -4.91458 0.53973 C 5.65828 1.64974 -0.24040 C 4.39546 2.08229 0.17714 C 3.40188 1.15043 0.48545 C 3.64203 -0.22549 0.37323 C 4.91963 -0.64751 -0.03145 C 5.91804 0.28069 -0.34145 H 6.43413 2.37440 -0.47481 H 4.18797 3.14479 0.27684 H 2.43964 1.50769 0.83751 H 5.13510 -1.71078 -0.10837 H 6.89851 -0.06862 -0.65533 2Ph_HCO_solv_boat_Z_Prox_TS Gradients converged E_sol = -928.04309187919 a.u. Zn 0.00222 0.00563 0.02815 C -0.00069 -0.03874 2.35736 C 1.37949 -0.00744 2.45190 C 2.32688 -0.96156 2.01634 C 2.92453 -0.25248 0.14644 N 1.95395 0.44424 -0.52751 H -0.55843 0.81130 2.74383 H -0.54148 -0.98364 2.34077 H 1.83999 0.93714 2.73753 H 3.29729 -0.94928 2.49877 H 3.71361 0.36884 0.57533 C 1.04575 -2.77851 1.05351 O 1.94355 -2.33509 1.90332 O 0.38739 -2.10889 0.25624 H 0.93361 -3.86348 1.13916 C 2.46549 4.64672 -0.99995 C 2.82708 4.05040 0.21104 C 2.67345 2.67361 0.40271 C 2.14738 1.86309 -0.62121 C 1.81441 2.47035 -1.84586 C 1.96096 3.84563 -2.03011 H 2.58204 5.71804 -1.14158 H 3.22846 4.65720 1.01949 H 2.96965 2.24230 1.35415 H 1.45695 1.84419 -2.65848 H 1.69361 4.28769 -2.98743 C 4.78405 -3.75209 -1.55725 C 3.60214 -3.25837 -2.11756 C 2.96857 -2.14509 -1.55896 C 3.50129 -1.51229 -0.42597 C 4.69553 -2.01429 0.12589 C 5.33235 -3.12127 -0.43351 H 5.28214 -4.61208 -1.99874 H 3.17839 -3.72988 -3.00126 H 2.07703 -1.73935 -2.02020 H 5.14050 -1.52074 0.98818 H 6.26083 -3.48634 -0.00112 2Ph_HCO_solv_boat_Z_Dist_TS Gradients converged E_sol = -928.03146609515 a.u. Zn -0.07149 0.10133 -0.08364 C -0.07475 -0.08056 2.22910 C 1.29309 -0.03231 2.44644 C 2.19097 -1.07924 2.12138 C 2.84703 -0.56129 0.31041 N 1.97377 0.24917 -0.40191 H -0.68214 0.76672 2.54339 H -0.57049 -1.05154 2.21911 H 1.76178 0.91960 2.69150 H 3.14125 -1.12269 2.64997 H 3.71091 -0.01334 0.69189 C 2.16514 -3.44021 2.43285 O 1.55777 -2.32459 1.96974 O 1.65447 -4.52300 2.30388 H 3.12562 -3.25244 2.93568 C 4.12800 -4.35004 -1.31365 C 2.97744 -3.73448 -1.81547 C 2.54915 -2.51398 -1.28861 C 3.25070 -1.89230 -0.24731 C 4.41193 -2.51525 0.24522 C 4.84786 -3.73264 -0.28425 H 4.46637 -5.29666 -1.72753 H 2.42006 -4.19831 -2.62561 H 1.67659 -2.02235 -1.70163 H 4.98884 -2.03566 1.03393 H 5.75273 -4.19587 0.10122 C 3.33402 4.27946 -0.64557 C 4.06547 3.22998 -1.21519 C 3.61200 1.91566 -1.11503 C 2.41197 1.61386 -0.43692 C 1.69944 2.67349 0.14718 C 2.14809 3.99455 0.03358 H 3.68796 5.30371 -0.72759 H 4.98804 3.43578 -1.75310 H 4.16720 1.10824 -1.58528 H 0.80572 2.46733 0.73136 H 1.57639 4.79494 0.49719 2Ph_HCO_solv_boat_E_Prox_TS Gradients converged E_sol = -928.03064300930 a.u. Zn -0.00654 0.00430 -0.00462 C 0.00860 0.03712 2.28951 C 1.35857 0.01508 2.62486 C 2.15490 -1.14363 2.43520 C 2.68435 -1.18784 0.49304 N 2.03175 -0.27123 -0.30011 H -0.56077 0.93513 2.52234 H -0.55062 -0.89655 2.35681 H 1.85428 0.94544 2.88514 H 3.70165 -0.88160 0.74587 H 1.62327 -2.08930 2.47814 C 4.30655 -0.38074 3.24306 O 3.34951 -1.32831 3.18306 O 4.26786 0.70016 2.70311 H 5.13346 -0.75474 3.86224 C 4.13125 3.38120 -0.91951 C 4.65562 2.16087 -1.36127 C 3.96819 0.96941 -1.13124 C 2.73501 0.97036 -0.45049 C 2.22931 2.19785 0.00539 C 2.91533 3.39301 -0.23422 H 4.66711 4.30914 -1.10366 H 5.59957 2.13660 -1.90097 H 4.36465 0.02856 -1.50451 H 1.31462 2.22219 0.59236 H 2.50389 4.33017 0.13395 C 2.55544 -5.34771 -0.70548 C 2.18867 -4.33584 -1.59576 C 2.22016 -2.99823 -1.18921 C 2.58967 -2.64660 0.11954 C 2.98904 -3.67476 0.99637 C 2.96768 -5.00863 0.58909 H 2.53503 -6.38891 -1.01840 H 1.89007 -4.58150 -2.61233 H 1.97746 -2.20989 -1.89217 H 3.33577 -3.43888 1.99792 H 3.27719 -5.78531 1.28446 2Ph_HCO_solv_boat_E_Dist_TS Gradients converged E_sol = -928.03466975511 a.u. Zn -0.00966 -0.02615 0.01538 C 0.03506 0.02181 2.34534 C 1.40975 0.01475 2.51945 C 2.23542 -1.14294 2.51886 C 2.02098 -2.02406 0.74145 N 1.71643 -1.14837 -0.27320 H -0.50020 0.95407 2.51833 H -0.53614 -0.89224 2.51027 H 1.93386 0.97084 2.49348 H 3.07216 -2.32260 0.75946 H 1.95654 -1.98452 3.14243 C 4.47367 -1.69602 3.10945 O 3.60208 -0.77744 2.66578 O 4.20616 -2.84536 3.38657 H 5.47230 -1.24739 3.18414 C -0.64282 -5.33891 1.50258 C -0.98596 -4.37364 0.55465 C -0.11933 -3.30463 0.30142 C 1.08136 -3.16098 1.00991 C 1.42399 -4.15202 1.95101 C 0.57421 -5.23059 2.18932 H -1.30705 -6.17797 1.69580 H -1.91432 -4.46075 -0.00502 H -0.35324 -2.60888 -0.49764 H 2.36465 -4.07745 2.49082 H 0.86038 -5.99065 2.91253 C 5.09077 0.85934 -1.91109 C 4.90453 -0.51400 -2.11182 C 3.80137 -1.16675 -1.56135 C 2.85806 -0.45456 -0.79655 C 3.06055 0.91797 -0.59013 C 4.16431 1.57241 -1.14724 H 5.94932 1.36590 -2.34506 H 5.61581 -1.07931 -2.70992 H 3.64798 -2.22919 -1.73556 H 2.36939 1.47565 0.03796 H 4.30287 2.63685 -0.97005