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page S1 Electronic Supplementary Information (ESI) for Chem. Commun. Nitric oxide coupling mediated by iron porphyrins: the N-N bond formation step is facilitated by electrons and a proton Jun Yi, Brian H. Morrow, Adam L. O. C. Campbell, Jana K. Shen, and George B. Richter-Addo Department of Chemistry and Biochemistry, University of Oklahoma, 11 Stephenson Parkway, Norman, OK 7319. USA. yijun@ou.edu; jana.k.shen@ou.edu; grichteraddo@ou.edu Part A: Complete reference for Gaussian-9 Part B: Coordinates of the Optimized Geometries i. [(P)Fe(NONO)] ii. [(P)Fe(NONO)] -1 iii. [(P)Fe(NONO)(Im)] // iv. -1 [(P)Fe(NONO)(Im)] // v. [(P)Fe(NONO)(Im)] vi. -1 [(P)Fe(NONO)(Im)] vii. [(P)Fe(NONOH)(Im)] viii. [(P)Fe(NONHO)(Im)] ix. [(P)Fe(NOHNO)(Im)] x. [(P)Fe(NOHNO)(Im)] // Part C: i. Fig. S1: Contour plots of α-spin orbitals for complexes [(P)Fe(NONO)(Im)] // and [(P)Fe(NONO)(Im)] // -1 ii. Fig. S2: Contour plots of β-spin orbitals for complexes [(P)Fe(NONO)(Im)] and [(P)Fe(NONO)(Im)] -1. iii. Fig. S3: Calculated spin densities, using the B3LYP/TZVP method, for selected atoms of [(P)Fe(NONO)(Im)] -1 and the products A-C that result from protonation. iv. Fig. S4: Variation in the SOMO of [(P)Fe(NONO)(Im)] -1 upon protonation to give product C.

page S2 Part A: Complete reference for Gaussian-9 Gaussian 9, Revision A.1 M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 29.

page S3 Part B: Coordinates of the Optimized Geometries: i. [(P)Fe(NONO)], E = -2512.67411 Hartree Fe -.73934.48 -.18256 N 1.574794-1.1262 -.47815 C 1.651617-2.54129 -.437996 C 3.19222-2.94487 -.583562 C 3.78123-1.82666 -.728626 C 2.88913 -.693511 -.65637 C 3.281331.631597 -.742678 C 2.427421 1.72918 -.64166 N 1.54823 1.64691 -.464283 C.63296 2.964694 -.389697 C 1.746743 3.868592 -.525495 C 2.861129 3.96897 -.69765 H 3.89163 3.414569 -.838538 H 1.66891 4.953658 -.51224 C -.691336 3.369828 -.26789 C -1.783423 2.513481 -.26337 N -1.713656 1.1316 -.33368 C -3.3325.75733 -.34424 C -3.93411 1.832993 -.299887 C -3.158373 2.95441 -.24657 H -3.47253 3.995482 -.2922 H -5.1916 1.757127 -.313833 C -3.44189 -.618791 -.374556 C -2.583955-1.795 -.388372 N -1.199343-1.63293 -.38528 C -.766253-2.9559 -.35672 C -1.89436-3.853861 -.358314 C -3.18385-3.84345 -.38727 H -4.5881-3.43761 -.45314 H -1.89762-4.938785 -.348975 C.561157-3.357736 -.351349 H.758688-4.43175 -.329951 H -4.514811 -.818462 -.376924 H -.889368 4.442114 -.217875 H 4.344655.832494 -.884674 H 4.855838-1.7445 -.878413 H 3.336467-3.984773 -.591746 N -.19274 -.3233 1.55429 O -.962137 -.11746 2.382772 N 1.618477.316 2.52185 O 1.338466 -.1181 3.619925

page S4 ii. [(P)Fe(NONO)] -1 : E = -2512.74952 Hartree Fe.7386.3 -.212198 N -1.335448 1.49927 -.47618 C -1.154787 2.78496 -.478592 C -2.419859 3.468619 -.61171 C -3.38369 2.51964 -.689196 C -2.74646 1.22972 -.63325 C -3.345987.449 -.663461 C -2.74856-1.22897 -.63623 N -1.335713-1.4952 -.47691 C -1.155433-2.7846 -.47956 C -2.42643-3.46792 -.611984 C -3.384111-2.5961 -.693 H -4.46786-2.619911 -.8722 H -2.538357-4.5513 -.641745 C.72624-3.42783 -.396476 C 1.33761-2.785138 -.347618 N 1.483933-1.49765 -.336219 C 2.86255-1.2379 -.299238 C 3.543513-2.52663 -.29881 C 2.575462-3.46851 -.328421 H 2.694654-4.559 -.338764 H 4.625498-2.62336 -.279529 C 3.51755 -.416 -.27263 C 2.86559 1.2397 -.299684 N 1.48432 1.49413 -.336624 C 1.34456 2.784833 -.347827 C 2.576329 3.46793 -.328696 C 3.544129 2.51792 -.299381 H 4.626155 2.621896 -.28286 H 2.695766 4.55259 -.33894 C.73449 3.42789 -.396234 H.7393 4.52398 -.42173 H 4.593944 -.553 -.24649 H.728-4.52391 -.42593 H -4.43381.548 -.763383 H -4.46268 2.621244 -.799628 H -2.537324 4.55864 -.64483 N.39276.514 1.594844 O.982336.244 2.344846 N -1.617557 -.29 2.521468 O -1.377124 -.88 3.689955

page S5 iii. [(P)Fe(NONO)(Im)] //, E = -2738.988492 Hartree Fe.52785.82 -.175727 N -1.384652-1.42189.8985 C -1.187651-2.786438.18425 C -2.453696-3.47527.14829 C -3.42162-2.51369.219295 C -2.74734-1.235318.134699 C -3.386639.248.195821 C -2.747164 1.23574.13473 N -1.384438 1.42512.9555 C -1.187352 2.786736.19227 C -2.45338 3.47561.148644 C -3.421384 2.514155.219285 H -4.497576 2.64135.31879 H -2.569695 4.557213.17659 C.4797 3.42712 -.78937 C 1.277819 2.782955 -.212611 N 1.472135 1.4169 -.25519 C 2.828549 1.234561 -.43736 C 3.53574 2.51356 -.49757 C 2.542298 3.472397 -.35464 H 2.65999 4.554174 -.351983 H 4.575372 2.641581 -.633547 C 3.465319 -.524354 C 2.828413-1.234533 -.437754 N 1.47219-1.416789 -.255619 C 1.27756-2.782819 -.213839 C 2.541861-3.472376 -.355938 C 3.53243-2.51391 -.49946 H 4.574986-2.641711 -.635429 H 2.659413-4.554169 -.354446 C.47535-3.42489 -.825 H.51364-4.512251 -.63317 H 4.546721 -.11 -.673584 H.5183 4.512468 -.61686 H -4.474177.317.29238 H -4.497771-2.64774.318415 H -2.5714-4.556813.175928 N -.61582.265-1.958692 O.73473.214-2.846584 N -1.81335.676-2.836854 O -1.548522.8-3.96436 N.231469 -.191 1.89795 C 1.41512 -.396 2.636781 C 1.9717 -.1264 3.976146 N -.287425 -.168 4.4871 C -.772559 -.137 2.768126 H -1.828426 -.1122 2.5184 H -.848265 -.244 4.88683 H 1.719171 -.1781 4.863848 H 2.37239.179 2.154298

page S6 iv. [(P)Fe(NONO)(Im)] // -1, E = -2739.52444 Hartree Fe -.471.5 -.179621 N 1.38995 1.417749 -.1846 C 1.192748 2.786882 -.3764 C 2.458967 3.474794.96871 C 3.42483 2.5155.189195 C 2.745854 1.234554.11542 C 3.383862 -.8.188635 C 2.745836-1.234563.115471 N 1.38978-1.417746 -.1843 C 1.192713-2.786877 -.3649 C 2.458923-3.47481.9732 C 3.424768-2.51565.189332 H 4.5233-2.633893.288184 H 2.576761-4.557575.14988 C -.3929-3.42657 -.138565 C -1.271636-2.787556 -.236835 N -1.46478-1.417713 -.249362 C -2.826968-1.23488 -.364789 C -3.57314-2.51573 -.416246 C -2.54454-3.475196 -.338359 H -2.657888-4.557892 -.35311 H -4.585359-2.634112 -.59353 C -3.466765.23 -.41489 C -2.826953 1.234846 -.364813 N -1.4646 1.417739 -.24944 C -1.27164 2.78758 -.236915 C -2.54415 3.475232 -.338446 C -3.57286 2.51617 -.416295 H -4.585331 2.634164 -.59393 H -2.657838 4.557929 -.353216 C -.3917 3.42672 -.138684 H -.38618 4.518948 -.142858 H -4.555244.28 -.511549 H -.38669-4.518934 -.14272 H 4.472179 -.13.287787 H 4.52367 2.633869.28828 H 2.57682 4.557568.1478 N.77114 -.34-2.6613 O -.859424.48-2.843186 N 1.65885 -.224-2.817289 O 1.4613 -.242-4.16334 N -.196681.4 1.93593 C -1.34679 -.65 2.73968 C -1.1328 -.84 4.38426 N.374447.199 4.71457 C.825461.173 2.78259 H 1.87455.293 2.498617 H.955891.325 4.92426 H -1.612961 -.191 4.94218 H -2.326469 -.179 2.237695

page S7 v. [(P)Fe(NONO)(Im)], E = -2738.988442 Hartree Fe.4454.9863 -.181274 N 1.63318-1.24812 -.39461 C 2.938158 -.91895 -.41485 C 3.748491-2.1345 -.533862 C 2.891275-3.166469 -.521757 C 1.555743-2.626939 -.38324 C.398579-3.39867 -.32824 C -.888848-2.9363 -.16858 N -1.21595-1.566635.592 C -2.57212-1.529497.25891 C -3.19886-2.87246.331 C -2.67666-3.72456.69539 H -2.7865-4.811723.22475 H -4.15514-3.114596.484287 C -3.328553 -.372557.417298 C -2.84179.92552.3527 N -1.526649 1.264576.59517 C -1.49821 2.643271 -.5431 C -2.82665 3.182485.194393 C -3.65798 2.117591.395149 H -4.729771 2.12687.582389 H -3.72766 4.242442.186 C -.35692 3.412845 -.18616 C.946248 2.915261 -.284221 N 1.293642 1.578778 -.25626 C 2.668624 1.54335 -.367661 C 3.199523 2.886671 -.449391 C 2.131447 3.736792 -.4294 H 2.128648 4.824131 -.444588 H 4.25611 3.129996 -.539933 C 3.439439.386574 -.42731 H 4.52742.56872 -.51629 H -.474485 4.497114 -.216345 H -4.39635 -.493298.611756 H.513391-4.481899 -.378267 H 3.12548-4.226263 -.61747 H 4.832574-2.17591 -.62643 N -.1714.31965-1.959391 O.661949.116342-2.866911 N.257793 -.6719 1.887636 C.263694 1.81195 2.742762 C.4493.648295 4.33631 N.557244 -.729988 3.94993 C.43741-1.87237 2.639782 H.483193-2.19743 2.28369 H.71634-1.368577 4.72532 H.512213 1.179274 4.976494 H.135531 2.9147 2.3792 N -1.876836 -.9368-2.784827 O -1.651165 -.47639-3.919788

page S8 vi. [(P)Fe(NONO)(Im)] -1, E = -2739.52594 Hartree Fe.2631.1536 -.18218 N 1.526521-1.314834 -.316877 C 2.878463-1.4447 -.415968 C 3.637851-2.266769 -.51926 C 2.734761-3.294747 -.491384 C 1.424572-2.693969 -.364817 C.23416-3.411418 -.27249 C -1.29548-2.851324 -.93925 N -1.293526-1.496677 -.12633 C -2.655852-1.3985.2257 C -3.256743-2.712716.25746 C -2.246831-3.616512.7735 H -2.34289-4.73752.38665 H -4.318371-2.9215.49657 C -3.36941 -.27874.341461 C -2.8985 1.64931.253825 N -1.46972 1.34743.5125 C -1.377119 2.719356.271 C -2.6827 3.32127.27824 C -3.569476 2.29175.35632 H -4.646183 2.341158.51271 H -2.87223 4.392192.21755 C -.1946 3.43946 -.135613 C 1.75266 2.879997 -.25393 N 1.348493 1.524175 -.25666 C 2.723664 1.42443 -.366782 C 3.323821 2.739275 -.42479 C 2.299613 3.643981 -.358711 H 2.35623 4.731712 -.38214 H 4.392518 2.92828 -.515141 C 3.438258.232887 -.427279 H 4.525355.33118 -.514854 H -.26752 4.529419 -.14971 H -4.439523 -.278383.5215 H.297769-4.5173 -.328638 H 2.92152-4.365954 -.55464 H 4.721784-2.317424 -.61281 N -.1456.4714-2.6799 O.77163.12966-2.862584 N -1.689236 -.51712-2.774973 O -1.574329 -.18587-3.97613 N.242299 -.295 1.92635 C.28274 1.38915 2.79844 C.455579.577844 4.82488 N.52187 -.841 3.972549 C.387739-1.127135 2.649711 H.484-2.14178 2.263314 H.646273-1.462323 4.73387 H.536411 1.8623 5.37131 H.184175 2.57862 2.43829

page S9 vii. [(P)Fe(NONOH)(Im)], E = -2379.58364 Hartree Fe.82.19243 -.128634 N 2.14215 -.29311 -.194565 C 2.87412 1.52665 -.226258 C 4.24257.63834 -.326248 C 4.2778 -.761689 -.371724 C 2.817489-1.14845 -.288681 C 2.366158-2.464388 -.279756 C 1.34479-2.85545 -.15635 N -.39371-1.989335 -.4729 C -1.15182-2.795324.12929 C -.76889-4.187684.92885 C.5871-4.222643 -.764 H 1.239847-5.9763 -.14329 H -1.46181-5.2594.19197 C -2.461447-2.344496.212959 C -2.851299-1.12891.14154 N -1.996783.638 -.4594 C -2.88411 1.177278 -.7712 C -4.19858.793398.245 C -4.224343 -.5651.168945 H -5.86734-1.21974.27565 H -5.3535 1.48815 -.9669 C -2.363744 2.4994 -.18888 C -1.28354 2.88398 -.214667 N.52559 2.24277 -.155355 C 1.173134 2.83338 -.191779 C.787349 4.222677 -.25841 C -.578741 4.252161 -.2813 H -1.237133 5.116356 -.34569 H 1.484636 5.56658 -.299987 C 2.48838 2.386894 -.2231 H 3.276794 3.1474 -.2363 H -3.119567 3.276478 -.243593 H -3.245957-3.9478.327847 H 3.11427-3.254869 -.366265 H 5.38642-1.45853 -.4627 H 5.17543 1.261916 -.373366 N.319.44611-2.19291 O.768296.773944-2.771975 N -.871995 -.76682-2.617874 O -.8141 -.675725-4.4843 N.12122.564 1.9488 C -.614944.868619 2.88166 C -.253292.59396 4.14248 N.7254 -.41157 4.1745 C.888529 -.7633 2.7254 H 1.58943-1.457368 2.33516 H 1.179752 -.85155 4.795375 H -.57741 1.2223 5.5327 H -1.334449 1.588924 2.435227 H -1.57537-1.319849-4.268683

page S1 viii. [(P)Fe(NONHO)(Im)], E = -2379.586474 Hartree Fe.37824.15668 -.152771 N 1.72186-1.6995 -.217951 C 3.16366 -.59576 -.24837 C 3.952515-1.693474 -.341141 C 3.212377-2.84224 -.382695 C 1.822527-2.444153 -.35376 C.751478-3.333621 -.286764 C -.58836-2.976686 -.154235 N -1.59398-1.68265 -.56849 C -2.42638-1.793.13628 C -2.818546-3.18427.143849 C -1.679651-3.917321 -.38224 H -1.57299-4.998932 -.88687 H -3.839683-3.538258.268794 C -3.39348 -.721346.241694 C -2.953288.62313.164519 N -1.664545 1.94377 -.17651 C -1.777394 2.47122 -.81654 C -3.16122 2.868289.5937 C -3.889841 1.72362.29876 H -4.96486 1.616473.33869 H -3.514173 3.897261.27675 C -.71635 3.3573 -.2341 C.633346 2.99668 -.233183 N 1.113936 1.73841 -.178885 C 2.489553 1.81373 -.216576 C 2.881767 3.24343 -.278278 C 1.73469 3.93813 -.295275 H 1.615672 5.1883 -.347759 H 3.91556 3.555974 -.316827 C 3.379797.746277 -.226346 H 4.445489.979915 -.26724 H -.94629 4.422227 -.248638 H -4.367511 -.953891.374624 H.981761-4.39834 -.363621 H 3.55955-3.868388 -.464542 H 5.343-1.582638 -.382627 N.38981.4488-2.58483 O.997693.237297-2.83727 N -1.189579 -.196181-2.693415 O -1.36424 -.2271-3.93417 N.138762.371 1.88958 C -.5643 1.71572 2.748161 C.13726.647844 4.4547 N.4619 -.71952 3.96929 C.413433-1.55237 2.6453 H.619938-2.56666 2.28357 H.58944-1.326282 4.7445 H.35831 1.16962 4.99268 H -.29568 2.6659 2.374789 H -1.957584 -.34853-2.1736

page S11 ix. [(P)Fe(NOHNO)(Im)], E = -2739.581979 Hartree Fe -.598.358 -.153264 N -.4226-2.5382 -.16577 C 1.31916-2.876496 -.167886 C.566555-4.242949 -.221522 C -.798918-4.194679 -.264181 C -1.171276-2.799454 -.2258 C -2.482732-2.333632 -.171466 C -2.85654-1.432 -.29658 N -1.986162.67333.4618 C -2.77646 1.185712.213586 C -4.172692.89942.27116 C -4.223269 -.54492.11377 H -5.97227-1.191574.82613 H -4.99656 1.59459.398326 C -2.31431 2.494484.275494 C -.986739 2.877331.11712 N.7212 2.12323 -.6614 C 1.186236 2.8756 -.233137 C.817682 4.2536 -.159936 C -.528451 4.247836.6728 H -1.169679 5.11968.177623 H 1.513288 5.34429 -.269854 C 2.491154 2.347919 -.392294 C 2.883126 1.12215 -.372597 N 2.22778 -.67646 -.26635 C 2.8365-1.191288 -.25563 C 4.225125 -.85619 -.281711 C 4.253314.557211 -.39483 H 5.11982 1.29491 -.481521 H 5.61867-1.574 -.264472 C 2.373239-2.52728 -.151147 H 3.118171-3.3277 -.139723 H 3.276182 3.98328 -.53387 H -3.54676 3.28554.47453 H -3.281547-3.7577 -.223898 H -1.54128-5.21394 -.3211 H 1.21415-5.116919 -.239942 N -.13742.72345-2.36823 O.8939 -.582942-2.87187 N -1.19173.568712-2.695752 O -1.167657.49564-3.935335 N.149291 -.45472 1.88361 C 1.96.684689 2.68286 C.79472.354116 3.997792 N -.21546 -.593475 3.982631 C -.58269 -.89276 2.688347 H -1.354723-1.52352 2.377999 H -.619357-1.52697 4.792549 H 1.25474.697811 4.916661 H 1.712481 1.392744 2.258482 H 1.529839 -.741951-2.222453

page S12 x. [(P)Fe(NOHNO)(Im)] //, E = -2739.581576 Hartree Fe.2929 -.8413 -.148733 N -1.623332-1.149684.7373 C -1.65281-2.525899.138617 C -3.18849-2.995173.243223 C -3.81859-1.8932.228134 C -2.94248 -.74382.11368 C -3.379393.574992.57848 C -2.54712 1.68417 -.61522 N -1.169131 1.636683 -.11718 C -.749874 2.94671 -.223794 C -1.889978 3.836996 -.22545 C -3.5194 3.54112 -.125348 H -4.498 3.359822 -.13913 H -1.8286 4.9249 -.32871 C.572896 3.37971 -.31123 C 1.69837 2.543843 -.326564 N 1.662325 1.1676 -.291557 C 2.991715.757968 -.39398 C 3.861475 1.9922 -.365989 C 3.55393 3.13623 -.376728 H 3.346761 4.61188 -.416817 H 4.947942 1.8628 -.39743 C 3.417326 -.567842 -.286984 C 2.574375-1.674436 -.21421 N 1.19576-1.625847 -.11138 C.778636-2.939288 -.33232 C 1.915596-3.829229 -.86991 C 3.29455-3.4569 -.198339 H 4.7589-3.352891 -.27287 H 1.852988-4.914779 -.49792 C -.541613-3.359912.9132 H -.7217-4.435492.142757 H 4.491176 -.754331 -.343631 H.748114 4.446875 -.369798 H -4.455959.7526.89557 H -4.94156-1.836711.274283 H -3.39134-4.41872.35689 N -.146996 -.97753-2.34888 O.99717 -.788-2.873344 N -1.268531 -.42815-2.685785 O -1.21645 -.53786-3.92384 N.148956.11188 1.88485 C 1.27667 -.89991 2.671544 C.935247.79138 3.99222 N -.41559.388754 3.995435 C -.855257.3981 2.78463 H -1.87659.61493 2.411335 H -.98579.577469 4.813761 H 1.517137.9574 4.93721 H 2.229793 -.34464 2.235762 H 1.646134.3775-2.239267

page S13 Part C: i. Fig. S1: Contour plots of α-spin orbitals for complexes [(P)Fe(NONO)(Im)] // and [(P)Fe(NONO)(Im)] // -1

page S14 ii. Fig. S2: Contour plots of β-spin orbitals for complexes [(P)Fe(NONO)(Im)] and [(P)Fe(NONO)(Im)] -1.

page S15 iii. Fig. S3: Calculated spin densities, using the B3LYP/TZVP method, for selected atoms of [(P)Fe(NONO)(Im)] -1 and the products A-C that result from protonation. iv. Fig. S4: Variation in the SOMO of [(P)Fe(NONO)(Im)] -1 upon protonation to give product C.

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