Reversible Interconversion between Singlet and Triplet Naphthyl Carbomethoxy Carbene by Zhendong Zhu, Thomas Bally,* Louise L. Stracener and Robert J. McMahon.* SUPPORTING INFORMATION ********************** Total energies, thermal corrections (at 298K), and cartesian coordinates of all stationary points located in this study. All numbers refer to B3LYP/ 6-31G* calculations. --------------------------------------------------------------------------- 1. E,E-Methyl alpaha-diazo-(2-naphthyl)acetate (E,E-MDA) [zhu/carb/indo/nap/nmda-n2f.out] HF=-761.3271916 Zero-point correction= 0.205412 Thermal correction to Energy= 0.219780 Thermal correction to Enthalpy= 0.220724 Thermal correction to Gibbs Free Energy= 0.162628 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -1.725427 0.481784 -0.000393 2 6 -2.559883 -0.730259 0.000477 3 6 -0.249674 0.538678 -0.000027 4 7 -2.393554 1.617551 -0.001439 5 8 -3.880902 -0.419053 0.000209 6 8 -2.142085 -1.872267 0.001356 7 6 0.519659 -0.614854 -0.000892 8 6 0.412181 1.804868 0.001234 9 7 -2.957316 2.606517 -0.002354 10 6 -4.774076 -1.544151 0.000906 11 6 1.936799 -0.550637 -0.000535 12 6 1.781657 1.888653 0.001534 13 1 0.037077 -1.583953 -0.001722 14 1 -0.169563 2.722281 0.002059 15 1 -5.776809 -1.116163 0.000533 16 1 -4.617892 -2.159461 -0.888971 17 1 -4.618043 -2.158256 0.891642 18 6 2.591661 0.722128 0.000666 19 6 4.009669 0.772507 0.000977 20 6 2.734404 -1.727757 -0.001389 21 6 4.108861 -1.647958 -0.001068 22 6 4.754078 -0.386578 0.000129 23 1 4.500007 1.743440 0.001907 24 1 2.237603 -2.694769 -0.002301 25 1 5.839641 -0.337723 0.000376 26 1 4.706137 -2.555829 -0.001737 27 1 2.262387 2.863967 0.002522 ---------------------------------------------------------- 2. Z,E-Methyl alpaha-diazo-(2-naphthyl)acetate (Z,E-MDA) [zhu/carb/indo/nap/nmda.out] HF=-761.3266617 Zero-point correction= 0.205337 Thermal correction to Energy= 0.219768 Thermal correction to Enthalpy= 0.220712 Thermal correction to Gibbs Free Energy= 0.161615 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -1.664129 0.367826 -0.004825 2 6 -2.853900 -0.497679 0.004590 3 8 -3.993713 0.239948 0.002875 4 6 -5.213907 -0.517679 0.012883 5 8 -2.845486 -1.713692 0.012970 6 1 -6.013251 0.223754 0.009749 7 1 -5.271726 -1.141898 0.908375 8 1 -5.277705 -1.155878 -0.872288 9 6 -0.247146 -0.054611 -0.004139 10 6 0.092753 -1.441141 -0.013622 11 6 1.409601 -1.833446 -0.013799 12 6 0.775920 0.883023 0.004672 13 6 2.138893 0.499751 0.004213 14 6 2.471889 -0.892750 -0.005111 15 6 3.191998 1.455710 0.013240 16 6 3.839034 -1.274970 -0.005211 17 1 -0.700203 -2.176526 -0.019768 18 1 1.650077 -2.894123 -0.020990 19 1 0.554427 1.947623 0.012945 20 6 4.836120 -0.325405 0.003600 21 6 4.507976 1.053322 0.012939 22 1 5.879273 -0.629788 0.003463 23 1 5.303025 1.794189 0.019846 24 1 4.086341 -2.334148 -0.012358 25 1 2.939203 2.513544 0.020495 26 7 -1.918843 1.660897 -0.013079 27 7 -2.102083 2.783603 -0.020178 ---------------------------------------------------------- 3. E,Z-Methyl alpaha-diazo-(2-naphthyl)acetate (E,Z-MDA) [zhu/carb/indo/nap/nmda-n1f.out] HF=-761.3234156 Zero-point correction= 0.205367 Thermal correction to Energy= 0.219757 Thermal correction to Enthalpy= 0.220701 Thermal correction to Gibbs Free Energy= 0.162583 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 1.857237 -0.626965 -0.095531 2 6 2.835245 0.471603 0.010418 3 6 0.381479 -0.635371 -0.004414 4 7 2.464202 -1.786141 -0.274498 5 8 2.251200 1.666486 0.248913 6 8 4.038496 0.315809 -0.093615 7 6 -0.292855 -1.852920 0.318120 8 6 -0.378361 0.500074 -0.237882 9 7 2.986840 -2.784339 -0.423784 10 6 3.166838 2.767354 0.385445 11 6 -1.661812 -1.907489 0.397096 12 6 -1.793694 0.472042 -0.150369 13 1 0.283837 -2.752190 0.515861 14 1 0.106944 1.435516 -0.486257 15 1 2.541659 3.638521 0.582731 16 1 3.742766 2.904240 -0.533377 17 1 3.855717 2.590598 1.214936 18 6 -2.458722 -0.754533 0.169223 19 6 -2.579790 1.633847 -0.383041 20 1 -2.152268 -2.845236 0.647355 21 6 -3.875480 -0.773784 0.247807 22 6 -3.953185 1.584026 -0.301392 23 1 -2.075156 2.565595 -0.627628 24 6 -4.608512 0.369338 0.017970 25 1 -4.541482 2.479726 -0.482143 26 1 -4.374184 -1.708709 0.493220 27 1 -5.693023 0.343609 0.080196 ---------------------------------------------------------- 4. Z,Z-Methyl alpaha-diazo-(2-naphthyl)acetate (Z,Z-MDA) [zhu/carb/indo/nap/nmda-syn1.out] HF=-761.3234178 Zero-point correction= 0.205434 Thermal correction to Energy= 0.219776 Thermal correction to Enthalpy= 0.220721 Thermal correction to Gibbs Free Energy= 0.162984 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -1.732809 0.667357 -0.158538 2 6 -3.021395 -0.004708 0.079331 3 6 -0.352972 0.132356 -0.160413 4 8 -2.867631 -1.320494 0.350300 5 8 -4.099578 0.560036 0.046328 6 6 -0.089773 -1.203086 -0.587772 7 6 0.714231 0.935855 0.210409 8 6 -4.091693 -2.030069 0.606694 9 6 1.195549 -1.686138 -0.620106 10 6 2.050511 0.465750 0.173252 11 1 -0.915962 -1.836667 -0.883835 12 1 0.541472 1.955422 0.548018 13 1 -3.791888 -3.060427 0.799796 14 1 -4.756119 -1.975988 -0.259440 15 1 -4.603580 -1.608110 1.475115 16 6 2.303387 -0.879317 -0.247256 17 6 3.150536 1.284017 0.549865 18 1 1.378207 -2.707360 -0.946891 19 6 3.641026 -1.352649 -0.277438 20 6 4.436933 0.795529 0.509829 21 1 2.958738 2.305455 0.870611 22 6 4.685978 -0.535086 0.091766 23 1 5.268867 1.431718 0.799730 24 1 3.826825 -2.375164 -0.597892 25 1 5.706328 -0.907691 0.064716 26 7 -1.882386 1.964177 -0.350588 27 7 -2.005081 3.082053 -0.515225 ---------------------------------------------------------- 5. Triplet Z,Z-(2-Naphthyl)carbomethoxycarbene (Z,Z-3NCC) [zhu/carb/indo/nap/nap-anti2f.out] HF=-651.7641111\S2=2.04 Zero-point correction= 0.193816 Thermal correction to Energy= 0.206398 Thermal correction to Enthalpy= 0.207342 Thermal correction to Gibbs Free Energy= 0.152760 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 1.931479 0.817095 -0.000039 2 6 2.987518 -0.160912 0.000091 3 6 0.533087 0.768213 -0.000060 4 8 4.215220 0.407223 -0.000080 5 8 2.804129 -1.374003 0.000203 6 6 -0.180201 -0.451161 -0.000049 7 6 -0.219155 1.999459 0.000017 8 6 5.314279 -0.515683 -0.000064 9 6 -1.592000 -0.473804 -0.000021 10 6 -1.584492 1.988741 0.000030 11 1 0.378500 -1.380944 -0.000082 12 1 0.328381 2.936867 0.000061 13 1 6.212476 0.102681 -0.000222 14 1 5.286698 -1.151085 0.889821 15 1 5.286539 -1.151311 -0.889781 16 6 -2.319591 0.763240 0.000010 17 6 -3.732602 0.727801 0.000029 18 6 -2.319167 -1.697211 -0.000045 19 6 -3.696683 -1.698283 -0.000048 20 6 -4.410108 -0.476512 0.000018 21 1 -4.282164 1.666289 0.000053 22 1 -1.765066 -2.632462 -0.000075 23 1 -5.496615 -0.488456 0.000024 24 1 -4.240812 -2.638687 -0.000059 25 1 -2.136915 2.925442 0.000062 ---------------------------------------------------------- 6. Triplet E,Z-(2-Naphthyl)carbomethoxycarbene (E,Z-3NCC) [zhu/carb/indo/nap/nap-tf.out] HF=-651.7640732\S2=2.04 Zero-point correction= 0.193828 Thermal correction to Energy= 0.206432 Thermal correction to Enthalpy= 0.207376 Thermal correction to Gibbs Free Energy= 0.152809 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 1.840227 -0.609117 -0.001216 2 6 3.142269 0.004108 -0.000192 3 8 4.139934 -0.909997 -0.000010 4 6 5.467328 -0.364219 0.000970 5 8 3.335623 1.215622 0.000400 6 1 6.135553 -1.225879 0.000983 7 1 5.633157 0.249555 0.890967 8 1 5.634145 0.250322 -0.888302 9 6 0.519897 -0.144717 -0.000607 10 6 0.201475 1.267238 -0.000621 11 6 -1.099746 1.682164 -0.000324 12 6 -0.543554 -1.068478 -0.000609 13 6 -1.891625 -0.650188 -0.000159 14 6 -2.187222 0.754228 0.000015 15 6 -2.969530 -1.578625 0.000084 16 6 -3.538231 1.169604 0.000281 17 1 1.022554 1.974289 -0.000452 18 1 -1.327734 2.745809 -0.000238 19 1 -0.316818 -2.131210 -0.000739 20 6 -4.564022 0.243480 0.000611 21 6 -4.276216 -1.141717 0.000526 22 1 -5.597676 0.578092 0.000955 23 1 -5.090791 -1.860578 0.000842 24 1 -3.759991 2.234198 0.000237 25 1 -2.743167 -2.642159 0.000080 ---------------------------------------------------------- 7. Triplet E,E-(2-Naphthyl)carbomethoxycarbene (E,E-3NCC) [zhu/carb/indo/nap/nap-t-syn-f.out] HF=-651.7593022\S2=2.041 Zero-point correction= 0.193430 Thermal correction to Energy= 0.206132 Thermal correction to Enthalpy= 0.207077 Thermal correction to Gibbs Free Energy= 0.151880 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 1.817405 -0.966682 -0.000266 2 6 3.219680 -0.652914 -0.000166 3 6 0.552394 -0.371160 -0.000216 4 8 3.467224 0.691852 0.000593 5 8 4.106659 -1.492538 -0.000668 6 6 0.374904 1.064873 -0.000482 7 6 -0.599370 -1.183267 0.000037 8 6 4.858816 1.049370 0.000698 9 6 -0.878317 1.608462 -0.000459 10 6 -1.898798 -0.631942 0.000075 11 1 1.257849 1.692592 -0.000709 12 1 -0.479921 -2.263143 0.000214 13 1 4.879167 2.139859 0.001520 14 1 5.358266 0.656268 -0.889054 15 1 5.358477 0.654916 0.889729 16 6 -2.052733 0.794561 -0.000173 17 6 -3.064207 -1.448187 0.000346 18 1 -0.998228 2.689579 -0.000660 19 6 -3.355477 1.343587 -0.000134 20 6 -4.320216 -0.882302 0.000375 21 1 -2.945422 -2.528915 0.000529 22 6 -4.468315 0.524723 0.000134 23 1 -5.202763 -1.515862 0.000584 24 1 -3.469520 2.425003 -0.000320 25 1 -5.463561 0.960461 0.000162 ---------------------------------------------------------- 8. Triplet Z,E-(2-Naphthyl)carbomethoxycarbene (Z,E-3NCC) [zhu/nap-carb.log.] HF=-651.7592762\S2=2.0 Zero-point correction= 0.193426 Thermal correction to Energy= 0.206116 Thermal correction to Enthalpy= 0.207060 Thermal correction to Gibbs Free Energy= 0.151837 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -1.449982 -0.448352 0.000087 2 6 -0.043716 -0.316705 0.000107 3 6 0.574778 0.952452 -0.000083 4 6 1.963404 1.114222 0.000215 5 6 3.191056 0.366827 0.000656 6 8 4.300775 0.876416 0.000521 7 8 2.992140 -0.986096 -0.000443 8 6 4.193796 -1.773574 -0.000507 9 1 3.861090 -2.812332 -0.001709 10 1 4.793547 -1.563639 0.889509 11 1 4.794606 -1.561918 -0.889396 12 6 -0.270363 2.122626 -0.000274 13 6 -1.630835 2.007327 -0.000293 14 6 -2.269997 0.729227 -0.000094 15 6 -2.082233 -1.723397 0.000234 16 6 -3.676226 0.585973 -0.000107 17 1 0.203774 3.099076 -0.000375 18 1 -2.253098 2.899234 -0.000438 19 1 0.578666 -1.204875 0.000090 20 6 -4.260437 -0.666076 0.000044 21 6 -3.455759 -1.829596 0.000217 22 1 -5.342803 -0.760524 0.000030 23 1 -3.925959 -2.809060 0.000334 24 1 -4.294608 1.480443 -0.000248 25 1 -1.459452 -2.614687 0.000367 ---------------------------------------------------------- 9. Singlet E-(2-Naphthyl)carbomethoxycarbene (E-1NCC) [zhu/carb/indo/nap/nap-t-sf.out] HF=-651.7568457 Zero-point correction= 0.193961 Thermal correction to Energy= 0.206717 Thermal correction to Enthalpy= 0.207661 Thermal correction to Gibbs Free Energy= 0.153328 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -1.823873 -1.031285 0.349935 2 6 -3.051094 -0.292835 0.288128 3 8 -3.702118 -0.326074 -0.897193 4 6 -5.015719 0.256604 -0.887935 5 8 -3.501564 0.215947 1.313399 6 1 -5.394254 0.133005 -1.903274 7 1 -4.972416 1.317482 -0.625189 8 1 -5.663381 -0.259017 -0.173676 9 6 -0.572521 -0.360731 0.289466 10 6 -0.392694 1.070322 0.247329 11 6 0.853101 1.618334 0.121329 12 6 0.569491 -1.173755 0.210119 13 6 1.862013 -0.635517 0.036577 14 6 2.012765 0.792158 -0.001074 15 6 3.014279 -1.461787 -0.078444 16 6 3.312287 1.331904 -0.154063 17 1 -1.269595 1.702938 0.344639 18 1 0.982717 2.697798 0.099940 19 1 0.426334 -2.249044 0.265661 20 6 4.410677 0.503221 -0.264430 21 6 4.263972 -0.904454 -0.225612 22 1 5.401498 0.933567 -0.381921 23 1 5.140636 -1.539495 -0.312923 24 1 3.433893 2.411634 -0.183355 25 1 2.887918 -2.540924 -0.047493 ---------------------------------------------------------- 10. Singlet Z-(2-Naphthyl)carbomethoxycarbene (Z-1NCC) [zhu/carb/indo/nap/naps2-f.out] HF=-651.7553852 (+0.91 kcal/mol) Zero-point correction= 0.193766 Thermal correction to Energy= 0.206583 Thermal correction to Enthalpy= 0.207527 Thermal correction to Gibbs Free Energy= 0.152904 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 1 5.272847 -0.863644 -0.224649 2 6 4.195998 -0.741619 -0.145385 3 1 4.279711 1.394437 -0.318374 4 6 3.644164 0.520831 -0.198741 5 6 2.012368 -1.746965 0.115893 6 6 2.242608 0.703361 -0.097374 7 6 3.375830 -1.887125 0.012864 8 6 1.408669 -0.457455 0.062442 9 6 1.637168 1.993487 -0.140467 10 1 3.830390 -2.872583 0.054256 11 1 -0.621221 -1.158386 0.268538 12 1 1.372715 -2.617174 0.239504 13 6 0.280805 2.134342 -0.019576 14 1 2.277408 2.864883 -0.253470 15 1 -0.192052 3.111017 -0.027176 16 6 -0.580683 0.989640 0.113336 17 6 -1.980414 1.210431 0.236966 18 6 0.013759 -0.285312 0.142356 19 6 -2.903074 0.116755 0.305857 20 8 -3.128565 -0.436115 1.381149 21 8 -3.578598 -0.141994 -0.839894 22 6 -4.648608 -1.092662 -0.716090 23 1 -5.397142 -0.742913 0.000277 24 1 -4.273247 -2.066389 -0.388195 25 1 -5.083646 -1.170635 -1.713243 ---------------------------------------------------------- 11. Transition state TS1 for the E-1NCC -> BHT-COOMe reaction [zhu/hasel/pcm/pcm-ts.out] HF=-651.7372429 Low frequencies --- -243.5799 -8.8281 -3.7612 -0.0014 -0.0008 -0.0004 4.7250 ****** 1 imaginary frequencies (negative signs) ****** Zero-point correction= 0.193145 Thermal correction to Energy= 0.205325 Thermal correction to Enthalpy= 0.206270 Thermal correction to Gibbs Free Energy= 0.153443 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 4.715131 -0.072355 -0.842573 2 1 4.403499 0.347480 -1.803451 3 8 3.694146 0.112134 0.151153 4 1 5.589749 0.457351 -0.462444 5 1 4.937761 -1.134305 -0.976581 6 6 2.527272 -0.542641 -0.100424 7 8 2.324414 -1.227858 -1.085869 8 6 1.600769 -0.380979 1.003764 9 6 -0.319399 -0.486753 1.286115 10 6 0.636179 0.560779 1.127908 11 6 0.292689 1.832824 0.542766 12 6 -1.536314 -0.412280 0.504310 13 1 -0.227657 -1.232948 2.061039 14 6 -0.925349 1.941839 -0.048837 15 6 -1.843058 0.823158 -0.142163 16 6 -2.465539 -1.468211 0.455203 17 1 1.014626 2.643263 0.528974 18 6 -3.059023 0.938413 -0.842637 19 1 -1.218318 2.873227 -0.528392 20 6 -3.654900 -1.330480 -0.245260 21 6 -3.949529 -0.123987 -0.901156 22 1 -2.230983 -2.400823 0.962037 23 1 -3.292677 1.875002 -1.343205 24 1 -4.357749 -2.157633 -0.290352 25 1 -4.880298 -0.020788 -1.451989 ---------------------------------------------------------- 11. 2,3-Benzobicyclo-[4.1.0]-hepta-2,4,6-triene (BHT-COOMe) [zhu/hasel/pcm/pcm-f.out] HF=-651.7566779 Zero-point correction= 0.194601 Thermal correction to Energy= 0.207018 Thermal correction to Enthalpy= 0.207962 Thermal correction to Gibbs Free Energy= 0.154594 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 1 -1.010773 -2.176904 1.493727 2 6 -1.583176 -1.539452 0.824245 3 6 -3.055304 0.101771 -0.880448 4 6 -1.138095 -0.234495 0.590112 5 6 -2.726941 -2.031336 0.198993 6 6 -3.461923 -1.208690 -0.662212 7 6 -1.901676 0.619709 -0.259959 8 6 0.040987 0.359657 1.287119 9 1 -3.045823 -3.054709 0.378384 10 1 -4.352045 -1.590271 -1.154800 11 6 -1.545621 2.024132 -0.469319 12 1 -3.632938 0.745975 -1.539863 13 6 0.482009 1.644505 0.617652 14 6 2.564909 0.159516 -0.032338 15 1 0.036397 0.282657 2.378262 16 6 -0.379021 2.576620 -0.045081 17 1 -2.241943 2.624536 -1.051134 18 6 1.362591 0.673007 0.611870 19 1 -0.095668 3.601549 -0.261250 20 8 3.462836 0.851628 -0.470514 21 8 2.563407 -1.194246 -0.057306 22 6 3.705384 -1.787420 -0.693461 23 1 3.794132 -1.444691 -1.728106 24 1 3.531778 -2.863444 -0.659608 25 1 4.622206 -1.528899 -0.156087 ---------------------------------------------------------- 12. Transition state TS2 for the BHT-COOMe -> BCH-COOMe reaction [zhu/hasel/pcm/pm-ts-f.out] HF=-651.7388896 Low frequencies --- -402.3999 -7.4527 -0.0008 -0.0004 -0.0003 5.9775 10.2069 ****** 1 imaginary frequencies (negative signs) ****** Zero-point correction= 0.192749 Thermal correction to Energy= 0.204930 Thermal correction to Enthalpy= 0.205874 Thermal correction to Gibbs Free Energy= 0.153569 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -4.499359 -0.278134 0.925662 2 1 -4.236515 -0.792122 1.854380 3 8 -3.334235 0.307254 0.324218 4 1 -5.173616 0.555021 1.126255 5 1 -4.965255 -0.995010 0.243966 6 6 -2.371395 -0.572543 -0.028266 7 8 -2.447033 -1.774281 0.125647 8 6 -1.213880 0.106716 -0.636411 9 6 0.025898 -0.389000 -1.218395 10 6 -0.790380 1.331558 -0.787363 11 6 0.071900 2.383193 -0.563926 12 6 1.273622 -0.371852 -0.513225 13 1 0.006793 -0.860284 -2.203614 14 6 1.206729 2.059129 0.162308 15 6 1.736506 0.738417 0.290762 16 6 2.150260 -1.479920 -0.676494 17 1 -0.140979 3.397919 -0.888337 18 6 2.939340 0.569616 1.039643 19 1 1.800280 2.867219 0.587332 20 6 3.317369 -1.593683 0.046108 21 6 3.704357 -0.568183 0.939099 22 1 1.840420 -2.284851 -1.338043 23 1 3.934945 -2.481665 -0.059444 24 1 4.617245 -0.667973 1.519573 25 1 3.261028 1.386083 1.681998 ---------------------------------------------------------- 13.Benzocycloheptatetraene (BCH-COOMe) [zhu/hasel/pcm1/pcm1-f.out] HF=-651.7512267 Zero-point correction= 0.193731 Thermal correction to Energy= 0.206290 Thermal correction to Enthalpy= 0.207234 Thermal correction to Gibbs Free Energy= 0.154435 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -3.474328 -1.503227 0.037199 2 6 -3.857823 -0.356724 0.798227 3 6 -3.023713 0.718779 0.883112 4 1 -4.825000 -0.337392 1.292715 5 6 -2.249174 -1.548017 -0.559205 6 1 -4.154723 -2.345813 -0.047611 7 6 -1.284362 -0.480109 -0.431481 8 1 -1.938627 -2.437861 -1.100170 9 6 -1.162520 2.029859 0.087107 10 1 -3.336799 1.607526 1.425028 11 6 0.024632 -0.790822 -0.793238 12 6 -1.748175 0.767400 0.207650 13 1 0.210298 -1.772993 -1.226484 14 6 -0.027903 2.299135 -0.742408 15 6 1.141759 0.058301 -0.488543 16 1 -1.676568 2.857130 0.579759 17 6 0.936651 1.370393 -0.699219 18 6 2.406050 -0.551904 -0.002678 19 1 0.041058 3.214091 -1.329606 20 8 2.574497 -1.751722 0.110748 21 8 3.348049 0.369332 0.290692 22 6 4.586639 -0.160809 0.783094 23 1 5.040908 -0.827980 0.045348 24 1 4.428089 -0.716935 1.711586 25 1 5.224601 0.705817 0.960206 ---------------------------------------------------------- 14. 3,4-benzobicyclo[4.1.0]hepta-2,4,6-triene (BBT-COOMe) [/zhu/hasel/pcm2/pcm2-f.out] HF=-651.7298708 (no thermal corrections available) ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 1 4.587682 -1.618209 -1.031868 2 6 3.754413 -.989928 -.728761 3 6 2.745918 -1.511390 .026424 4 6 3.734171 .387925 -1.125838 5 6 2.706832 1.198387 -.747189 6 1 4.551029 .781300 -1.724353 7 6 1.622284 -.710502 .433780 8 1 2.697109 2.246959 -1.034369 9 1 2.758450 -2.558070 .320145 10 6 .562185 -1.276674 1.133964 11 6 1.606436 .710068 .048368 12 6 .668152 1.597743 .560434 13 6 -.437499 1.155081 1.382387 14 1 .879134 2.663734 .479116 15 1 .572038 -2.315485 1.449962 16 6 -.538516 -.428585 1.315267 17 6 -1.549037 .274675 .866375 18 1 -5.080551 -.121652 -.919504 19 1 -.629521 1.704436 2.308136 20 6 -2.600839 .305975 -.141952 21 1 -4.816518 -1.896730 -.984083 22 8 -2.852570 1.260693 -.849642 23 8 -3.278242 -.867614 -.170388 24 6 -4.356652 -.916901 -1.117422 25 1 -3.979455 -.806165 -2.137958 ---------------------------------------------------------- 15. Transition state TS1 for the NCC -> BHT conversion *in the parent compound* (all other structures on that sur- face can be found in the paper by Xie et al. Ref. ) [zhu/hasel/pcm/mm-ts1f.out] HF=-423.848671711 Zero-point correction= 0.149120 Thermal correction to Energy= 0.156654 Thermal correction to Enthalpy= 0.157598 Thermal correction to Gibbs Free Energy= 0.116912 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -0.768150 1.685229 -0.107493 2 6 0.366783 0.788443 -0.019795 3 6 -2.046487 1.227525 -0.165312 4 1 -0.569895 2.754130 -0.065228 5 6 0.170340 -0.622631 -0.119563 6 6 1.677126 1.282943 0.130841 7 1 -2.894900 1.905506 -0.146197 8 6 -2.256042 -0.199591 -0.171194 9 6 1.290207 -1.476768 -0.101823 10 6 -2.939075 -1.150100 0.526697 11 6 -1.173169 -1.110638 -0.349450 12 1 -1.317741 -2.095222 -0.766278 13 1 -3.304555 -0.841348 1.517608 14 6 2.570305 -0.964505 0.049769 15 6 2.763411 0.420955 0.172796 16 1 1.828650 2.356682 0.214455 17 1 1.135325 -2.548780 -0.196868 18 1 3.424565 -1.635409 0.075791 19 1 3.767048 0.819266 0.293888 ---------------------------------------------------------- 16. 1-(2-Naphthyl)-2-methoxy oxirene (NMO) HF=-651.706916 Low frequencies --- -421.6397 -4.6296 -.0010 -.0006 .0004 4.4297 12.1971 ****** 1 imaginary frequencies (negative signs) ****** Zero-point correction= .191917 Thermal correction to Energy= .204571 Thermal correction to Enthalpy= .205515 Thermal correction to Gibbs Free Energy= .151704 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -1.972514 -.200944 -.291148 2 6 -.587868 .159282 -.203566 3 1 .028117 -1.886622 -.154141 4 6 .357325 -.851809 -.126681 5 6 1.151432 1.841655 -.070189 6 6 1.736185 -.548588 -.011638 7 6 -.178339 1.525766 -.173699 8 6 2.146957 .825625 .015768 9 6 2.728708 -1.562736 .072428 10 1 -.929796 2.307628 -.240030 11 6 -3.225979 .055896 -.452984 12 1 1.465368 2.882532 -.051475 13 1 -4.998649 -1.123199 .974202 14 1 -6.099498 .301951 .914193 15 8 -4.448409 .454954 -.279499 16 6 -5.063668 -.033415 .953443 17 1 -4.543183 .396891 1.813842 18 6 3.528226 1.126851 .125691 19 8 -2.601888 -1.469390 -.384020 20 1 2.414672 -2.603398 .050463 21 1 4.811179 -2.021420 .240809 22 1 3.837009 2.169451 .145918 23 6 4.466431 .120140 .205337 24 6 4.062343 -1.236600 .178093 25 1 5.521729 .364936 .289234 ---------------------------------------------------------- 17. (2-Naphthoyl)methoxycarbene (NMC) [zhu/carb/indo/nap/nap-sf.out] HF=-651.7552435 Zero-point correction= 0.193686 Thermal correction to Energy= 0.206466 Thermal correction to Enthalpy= 0.207410 Thermal correction to Gibbs Free Energy= 0.153207 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -2.009847 0.839936 -0.297882 2 6 -3.190635 -0.041332 -0.507706 3 8 -3.871144 -0.181548 0.588914 4 6 -5.135766 -0.882931 0.484942 5 8 -2.229727 2.051683 -0.324537 6 1 -5.918813 -0.182465 0.783633 7 1 -5.100588 -1.722130 1.183214 8 1 -5.272472 -1.219604 -0.544350 9 6 -0.648891 0.245953 -0.257843 10 6 -0.457180 -1.158974 -0.373389 11 6 0.803989 -1.697271 -0.289622 12 6 0.439765 1.076302 -0.063715 13 6 1.750659 0.551259 0.030123 14 6 1.940523 -0.866790 -0.085320 15 6 2.885703 1.383846 0.233306 16 6 3.256930 -1.390759 0.005915 17 1 -1.316783 -1.800801 -0.548706 18 1 0.950884 -2.770421 -0.384821 19 1 0.271067 2.146440 0.021511 20 6 4.334918 -0.556621 0.202744 21 6 4.148345 0.843657 0.317437 22 1 5.337171 -0.970856 0.271309 23 1 5.008709 1.488900 0.471882 24 1 3.400583 -2.465003 -0.082381 25 1 2.736139 2.457203 0.319751 ---------------------------------------------------------- 18. 2-(2-napththyl)propiolactone (NPL) [zhu/hasel/nlacton/nlacton-f.out] HF=-651.8486342 Zero-point correction= 0.197289 Thermal correction to Energy= 0.208564 Thermal correction to Enthalpy= 0.209508 Thermal correction to Gibbs Free Energy= 0.158715 ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 6 -2.239437 -0.360783 0.655845 2 8 -3.684683 1.496055 -0.331381 3 1 -2.204709 -2.096100 -0.764254 4 6 -2.840424 -1.610587 -0.021162 5 8 -3.853041 -0.779398 -0.683736 6 6 -0.799591 0.025723 0.408983 7 1 -2.476897 -0.313076 1.727054 8 6 -3.326265 0.369836 -0.150496 9 1 -3.315480 -2.346475 0.630831 10 1 -0.054858 -1.986963 0.376931 11 6 0.190482 -0.929289 0.302403 12 6 0.854815 1.782442 0.127423 13 6 1.550160 -0.568832 0.105276 14 6 -0.452677 1.402485 0.318573 15 6 1.892834 0.818950 0.016534 16 6 2.582372 -1.538946 -0.004667 17 1 -1.238091 2.149248 0.384111 18 1 3.508409 2.234777 -0.250451 19 1 1.108769 2.837126 0.052110 20 6 3.891348 -1.156574 -0.193510 21 1 2.321080 -2.592489 0.064524 22 1 4.671595 -1.908527 -0.274753 23 6 4.229966 0.216160 -0.283082 24 1 5.266629 0.504837 -0.433551 25 6 3.252308 1.180147 -0.180722 ---------------------------------------------------------- - - - - - - 2.CBH in zhu/hasel/chta/chta-f.out HF=-651.774821306 ZPVE=122.07175 (Kcal/Mol) Standard orientation: ---------------------------------------------------------- Center Atomic Coordinates (Angstroms) Number Number X Y Z ---------------------------------------------------------- 1 1 3.059377 2.337297 -0.452847 2 6 2.931245 1.259307 -0.399769 3 6 2.608225 -1.492329 -0.203543 4 6 1.781970 0.750038 0.229059 5 6 3.896466 0.414595 -0.929587 6 6 3.730214 -0.973084 -0.831342 7 6 1.591572 -0.664640 0.327615 8 6 0.811368 1.640200 0.892505 9 1 4.782894 0.827950 -1.402952 10 1 4.482598 -1.643595 -1.237438 11 1 0.730700 -2.367380 1.312216 12 1 2.491203 -2.570577 -0.125780 13 6 -0.449447 1.279818 0.765125 14 1 1.150150 2.477185 1.500165 15 6 -1.318920 0.281248 0.625998 16 6 -0.826617 -0.998053 1.147655 17 6 -2.580334 0.427772 -0.144026 18 6 0.471632 -1.362518 0.979380 19 1 -1.517493 -1.700063 1.609444 20 8 -2.991411 1.461417 -0.628831 21 8 -3.237538 -0.755547 -0.231089 22 6 -4.478800 -0.708937 -0.950092 23 1 -4.876507 -1.723828 -0.914060 24 1 -4.311600 -0.398239 -1.984948 25 1 -5.171171 -0.006209 -0.478306 ----------------------------------------------------------