Copyright The Royal Society of Chemistry, 1999 Supplementary Material Molecular structures of the compounds in xyz g94 format. -------------------------------------------------- Thioamide 1 gas-phase -------------------------------------------------- B3LYP/6-31G(d) C,0,-1.4868154078,-1.1900802846,0.0001769909 C,0,-2.2423993115,-0.0523376092,0.0001226807 C,0,-1.5608094883,1.196834342,0.0000884216 C,0,-0.1906179579,1.2529161326,-0.000110249 C,0,0.6147221553,0.0649281418,-0.0010056828 N,0,-0.1263315245,-1.1100121323,-0.0002225276 S,0,2.292356705,0.0050718043,0.0002848238 H,0,0.4294030452,-1.9593271337,-0.0000730791 H,0,0.3361575853,2.1997151387,0.0001856776 H,0,-1.9027022657,-2.1913507326,0.0005079679 H,0,-3.3238691215,-0.1120014351,0.0003968293 H,0,-2.1368557904,2.1183358853,0.0003501492 HF/6-311+G(2d,p) C,0,-1.4729202971,-1.1708667894,0.0001575598 C,0,-2.2203723555,-0.0590802888,0.0002444147 C,0,-1.5353330907,1.1891382991,0.0001730518 C,0,-0.188972407,1.245639404,0.0000259034 C,0,0.5970189906,0.0504180821,-0.0000588683 N,0,-0.1205871009,-1.0957156356,0.0000111077 S,0,2.2684328518,0.0044748088,-0.0002526319 H,0,0.415382203,-1.9353145425,-0.0000522572 H,0,0.3365499887,2.1780396847,-0.0000308624 H,0,-1.8854371689,-2.1604257676,0.0001974481 H,0,-3.2895315887,-0.1163507323,0.0003604847 H,0,-2.1043043998,2.1009716243,0.000237175 B3LYP/6-311+G(2d,p) C,0,-1.4840047669,-1.1840594776,0.0001584036 C,0,-2.2345288781,-0.0499465744,0.0002450558 C,0,-1.5521385664,1.1945324052,0.0001740318 C,0,-0.1877447237,1.2484338879,0.000023339 C,0,0.6113811345,0.0619974744,-0.0000687547 N,0,-0.1272568094,-1.1090772887,0.0000088426 S,0,2.2844522178,0.0048032606,-0.0002482946 H,0,0.4249595408,-1.9578385705,-0.000054649 H,0,0.3382565837,2.1923896596,-0.0000317895 H,0,-1.904218734,-2.1805690044,0.0002006053 H,0,-3.3129970479,-0.1082369172,0.0003631621 H,0,-2.1242233592,2.1151973912,0.0002410326 MP2/6-311+G(2d,p) C,0,-1.4839371103,-1.1891832911,0.0001587631 C,0,-2.2372733869,-0.0476830344,0.0002451465 C,0,-1.5581411502,1.1959666905,0.0001748513 C,0,-0.1859222254,1.2453186722,0.0000239486 C,0,0.6184874371,0.060871653,-0.0000697397 N,0,-0.1265677599,-1.1053530034,0.0000093425 S,0,2.2839060979,0.0056682709,-0.0002491154 H,0,0.4293951764,-1.9563483329,-0.0000538758 H,0,0.3408891597,2.191988644,-0.0000300102 H,0,-1.9012374538,-2.1890212091,0.0002016168 H,0,-3.317435415,-0.1120613829,0.0003639038 H,0,-2.1274160995,2.1204768295,0.0002409945 MP2(full)/6-311+G(2d,p) C,0,-1.4817925,-1.1872224324,0.0001584592 C,0,-2.2342381355,-0.0475387597,0.0002454028 C,0,-1.5561113498,1.1937972227,0.0001749237 C,0,-0.1860343011,1.2431830695,0.0000247615 C,0,0.6175775929,0.0610759893,-0.0000654627 N,0,-0.1264688289,-1.1036770259,0.0000104784 S,0,2.2810691392,0.005690581,-0.000251289 H,0,0.4291047872,-1.9539646069,-0.0000538889 H,0,0.3397539549,2.1896425062,-0.0000307829 H,0,-1.8988922183,-2.1864409188,0.0002001008 H,0,-3.3137627235,-0.1124415294,0.0003633918 H,0,-2.1244360639,2.1181238981,0.0002399472 Thioamide 1 (charge +1) gas-phase -------------------------------------------------- UB3LYP/6-311+G(2d,p) C,0,-1.4574311348,-1.2006499219,0.000156331 C,0,-2.219883027,-0.0407833378,0.000243331 C,0,-1.5730741119,1.1908957387,0.0001759717 C,0,-0.1823574899,1.2473220449,0.0000229577 C,0,0.5738712964,0.0684436121,-0.0000642108 N,0,-0.1238739108,-1.1171512349,0.0000095753 S,0,2.2860273363,0.0129125128,-0.0002495409 H,0,0.4348603628,-1.9680421931,-0.0000540866 H,0,0.3432138514,2.1921779735,-0.00003161 H,0,-1.8860398176,-2.1941332495,0.0002006675 H,0,-3.29861983,-0.1158106648,0.0003616867 H,0,-2.1494877687,2.1078977588,0.0002426872 -------------------------------------------------- Thioimidate 2a gas-phase -------------------------------------------------- HF/6-31G(d) C,0,-1.166647,-1.472691,0.000000 C,0,-0.021202,-2.242156,0.000000 C,0,1.199505,-1.582331,0.000000 C,0,1.220404,-0.203935,0.000000 C,0,0.000000,0.466559,0.000000 N,0,-1.162330,-0.148148,0.000000 H,0,2.145454,0.341460,0.000000 S,0,0.000715,2.244208,0.000000 H,0,-1.315410,2.381161,0.000000 H,0,-2.137503,-1.935597,0.000000 H,0,-0.081509,-3.314156,0.000000 H,0,2.121471,-2.135833,0.000000 B3LYP/6-31G(d) C,0,-1.1752769228,-1.4888485256,0. C,0,-0.0149848515,-2.2586294215,0. C,0,1.2129730179,-1.591855612,0. C,0,1.2307067363,-0.2021346588,0. C,0,0.,0.4729622831,0. N,0,-1.1810880057,-0.1481623525,0. H,0,2.1655934562,0.349701717,0. S,0,0.0003778227,2.2615824217,0. H,0,-1.3433661508,2.3663146958,0. H,0,-2.1555384115,-1.9621824611,0. H,0,-0.0718755311,-3.3424008903,0. H,0,2.1462496341,-2.1485797312,0. HF/6-311+G(2d,p) C,0,-1.1726762698,-1.4643305013,0. C,0,-0.0344914955,-2.2374872647,0. C,0,1.1866683282,-1.5843660125,0. C,0,1.2139813482,-0.2107761293,0. C,0,0.,0.4652159923,0. N,0,-1.1614432307,-0.1421150157,0. H,0,2.1408829147,0.3296446605,0. S,0,0.0167352807,2.240093569,0. H,0,-1.2997452316,2.3879674198,0. H,0,-2.1445809767,-1.9239643315,0. H,0,-0.1005409253,-3.3080950354,0. H,0,2.1054308764,-2.1417812148,0. B3LYP/6-311+G(2d,p) C,0,-1.1808642647,-1.4808529912,0. C,0,-0.0273772294,-2.2516729907,0. C,0,1.199052502,-1.5918975475,0. C,0,1.2223338494,-0.2080715378,0. C,0,0.,0.4730537923,0. N,0,-1.1775994709,-0.1440904995,0. H,0,2.1579473882,0.3368620564,0. S,0,0.0155835409,2.2555816027,0. H,0,-1.3223067819,2.3713056606,0. H,0,-2.1600247965,-1.9494030178,0. H,0,-0.0882599231,-3.3322012942,0. H,0,2.1276346122,-2.1505879027,0. MP2/6-311+G(2d,p) C,0,-1.1789472345,-1.4869109243,0. C,0,-0.0171846416,-2.252611981,0. C,0,1.2108733853,-1.5901297508,0. C,0,1.2239271283,-0.2013997606,0. C,0,0.,0.4790093246,0. N,0,-1.1851557635,-0.142411772,0. H,0,2.158290009,0.3504917433,0. S,0,0.0074766242,2.2537771337,0. H,0,-1.3248774817,2.3388424509,0. H,0,-2.1569002801,-1.9600682489,0. H,0,-0.0755645344,-3.3353407263,0. H,0,2.1435048192,-2.1452184009,0. MP2(full)/6-311+G(2d,p) C,0,-1.1765354382,-1.4857565661,0. C,0,-0.0159585722,-2.2497665368,0. C,0,1.2097982755,-1.5873971207,0. C,0,1.2220942922,-0.2006310602,0. C,0,0.,0.4785417145,0. N,0,-1.1827482348,-0.1434145449,0. H,0,2.1557613101,0.3512509345,0. S,0,0.006129396,2.2513094998,0. H,0,-1.3257977791,2.3346285743,0. H,0,-2.153743522,-1.9593836727,0. H,0,-0.07377605,-3.3319268118,0. H,0,2.1423320058,-2.1415617906,0. Thioimidate 2a (charge +1) gas-phase -------------------------------------------------- UB3LYP/6-311+G(2d,p) C,0,-1.2126400986,-1.4335268997,0. C,0,-0.0263319353,-2.2198735269,0. C,0,1.2125797664,-1.5877666485,0. C,0,1.2435662678,-0.2059003661,0. C,0,0.,0.485751625,0. N,0,-1.204555079,-0.1197028224,0. H,0,2.1784296092,0.3412727668,0. S,0,0.0267759088,2.2059899864,0. H,0,-1.3197815727,2.3437732884,0. H,0,-2.1851092577,-1.9146142278,0. H,0,-0.1041662586,-3.2999871776,0. H,0,2.1310544906,-2.1604697793,0. -------------------------------------------------- Thioimidate 2b gas-phase -------------------------------------------------- HF/6-31G(d) C,0,-1.450205,-1.201876,0.000103 C,0,-2.242725,-0.070817,0.000076 C,0,-1.606414,1.160402,0.000029 C,0,-0.227107,1.209807,-0.000051 C,0,0.466832,0.003514,-0.000203 N,0,-0.128495,-1.169601,-0.000048 H,0,0.292168,2.149086,-0.000004 S,0,2.241299,-0.094637,-0.000004 H,0,2.488256,1.207253,0.000348 H,0,-1.893712,-2.181643,0.000115 H,0,-3.313286,-0.151359,0.000134 H,0,-2.177030,2.071873,0.000085 B3LYP/6-31G(d) C,0,-1.462992,-1.213559,0.000003 C,0,-2.259230,-0.070065,0.000084 C,0,-1.619615,1.170982,-0.000017 C,0,-0.229436,1.221245,-0.000062 C,0,0.472832,0.005956,-0.000193 N,0,-0.124825,-1.187216,-0.000111 H,0,0.293874,2.172023,-0.000050 S,0,2.258154,-0.095072,0.000095 H,0,2.491937,1.234335,-0.000168 H,0,-1.913944,-2.204289,0.000086 H,0,-3.341542,-0.149908,0.000309 H,0,-2.196369,2.092157,0.000197 HF/6-311+G(2d,p) C,0,1.4488942925,-1.1983312356,0.0000853526 C,0,2.2382716505,-0.0693515009,0.0000494809 C,0,1.6011719464,1.1584658145,0.0000081386 C,0,0.226263009,1.2059451291,-0.0000451228 C,0,-0.4652580059,0.0018739538,-0.0001481151 N,0,0.1296134318,-1.1667796222,-0.0000253064 H,0,-0.2933712323,2.1438467923,-0.0000225284 S,0,-2.237421974,-0.0950274298,0.0000009989 H,0,-2.48462474,1.207880434,0.0002706763 H,0,1.8951994077,-2.1765867011,0.0000914004 H,0,3.3080397179,-0.1491794263,0.0000861433 H,0,2.1701570516,2.0703221672,0.0000370649 B3LYP/6-311+G(2d,p) C,0,-1.4628370248,-1.2090064792,0.0000589723 C,0,-2.2522550983,-0.067435993,0.0000413841 C,0,-1.6116665817,1.1682301925,0.0000052454 C,0,-0.2274594152,1.2154051939,-0.0000446269 C,0,0.472539399,0.0041420377,-0.0001404191 N,0,-0.128126888,-1.1820521346,-0.0000759685 H,0,0.2950432576,2.1629864194,-0.0000578032 S,0,2.2525219842,-0.0957732212,0.000041 H,0,2.4834201068,1.2279112576,0.0002010799 H,0,-1.9153180185,-2.1956493574,0.0000375872 H,0,-3.3317040934,-0.1445190003,0.0001015372 H,0,-2.1848324578,2.0879974503,0.0000700436 MP2-fc/6-311+G(2d,p) C,0,1.4657125596,-1.2124530043,0.0000555643 C,0,2.253491023,-0.0647944742,0.0000302335 C,0,1.6132291079,1.1741290469,-0.0000011246 C,0,0.2241171878,1.2145621381,-0.0000349218 C,0,-0.4787067236,0.0035672408,-0.0001034557 N,0,0.1233250851,-1.1916804394,-0.0000194632 H,0,-0.3017231336,2.1632480239,-0.0000105661 S,0,-2.2507495049,-0.0932905517,0.0000088015 H,0,-2.457003436,1.2256394508,0.0001818679 H,0,1.9203561734,-2.1991650972,0.0000709881 H,0,3.3350382214,-0.1421389475,0.0000556226 H,0,2.1849897296,2.0967627894,0.0000197321 MP2(full)/6-311+G(2d,p) C,0, 1.463910,-1.210851,0.000044 C,0,2.250623,-0.064873,0.000022 C,0,1.611214,1.172218,-0.000004 C,0,0.224099,1.212815,-0.000031 C,0,-0.478223,0.004103,-0.000084 N,0,0.123616,-1.189124,-0.000015 H,0,-0.301219,2.161087,-0.000012 S,0,-2.248176,-0.093573,0.000012 H,0,-2.455692,1.224636,0.000139 H,0,1.918456,-2.197099,0.000054 H,0,3.331555,-0.142437,0.000041 H,0,2.182660,2.094375,0.000012 -------------------------------------------------- -------------------------------------------------- Thioamide 1 liquid-phase -------------------------------------------------- B3LYP/6-31G(d) SCIPCM Dielectric=2.28 C,0,-1.4879294207,-1.1892664776,0.0001544345 C,0,-2.2429604554,-0.0491934081,0.000246877 C,0,-1.5618516116,1.1966033677,0.000171981 C,0,-0.1892362071,1.2502068019,0.0000177324 C,0,0.6092110571,0.0626600228,-0.0000637806 N,0,-0.1281583459,-1.1100945902,0.0000028311 S,0,2.2963558483,0.005717275,-0.0002423577 H,0,0.4185190939,-1.9656388118,-0.0000642119 H,0,0.3366907458,2.1972789123,-0.0000430967 H,0,-1.9034921696,-2.189958413,0.0001944829 H,0,-3.3243005398,-0.1078766112,0.0003700011 H,0,-2.1354024555,2.1193188148,0.0002372646 B3LYP/6-31G(d) Onsager 2.28 A0=4.24 C,0,-1.4834153304,-1.188642102,0.0001589645 C,0,-2.2403244116,-0.0521843885,0.0002454779 C,0,-1.5603921998,1.1949119047,0.0001746916 C,0,-0.1895697239,1.2509439147,0.000024076 C,0,0.6104705988,0.0641218078,-0.0000690008 N,0,-0.1250816354,-1.1079561539,0.0000089587 S,0,2.2903508037,0.0055543118,-0.0002494188 H,0,0.4283615428,-1.9570391895,-0.0000544322 H,0,0.3373252172,2.1964498217,-0.0000302848 H,0,-1.8997768289,-2.1885709479,0.000202008 H,0,-3.3202365884,-0.1141445405,0.0003640022 H,0,-2.1363283528,2.1152221246,0.00024144 -------------------------------------------------- Thioimidate 2a liquid-phase -------------------------------------------------- B3LYP/6-31G(d) SCIPCM Dielectric=2.28 C,0,-1.1748690031,-1.4909306264,0. C,0,-0.013810645,-2.259418517,0. C,0,1.2139383029,-1.5918177804,0. C,0,1.2309414211,-0.2016623352,0. C,0,0.,0.4722521599,0. N,0,-1.1813989933,-0.1491899636,0. H,0,2.1657826843,0.350001502,0. S,0,-0.0008025055,2.2628757517,0. H,0,-1.3436369315,2.3744896545,0. H,0,-2.1542076663,-1.9658251033,0. H,0,-0.0698624998,-3.3430278365,0. H,0,2.1473569987,-2.1478579048,0. B3LYP/6-31G(d) Onsager 2.28 A0=4.16 C,0,-1.1805203441,-1.4838111127,0. C,0,-0.0228938683,-2.255809704,0. C,0,1.2063878832,-1.5931269816,0. C,0,1.2273421829,-0.2045170858,0. C,0,0.,0.4744201618,0. N,0,-1.179890505,-0.1442671101,0. H,0,2.1628424847,0.3441136774,0. S,0,0.009452826,2.2574585615,0. H,0,-1.3296922768,2.3668900867,0. H,0,-2.1609415282,-1.9536936817,0. H,0,-0.0831703698,-3.338062074,0. H,0,2.1370548875,-2.1516468875,0. -------------------------------------------------- Thioimidate 2b liquid-phase -------------------------------------------------- B3LYP/6-31G(d) SCIPCM Dielectric=2.28 C,0,-1.4654424433,-1.2131824492,0.0001773205 C,0,-2.2595081878,-0.0683923777,0.0001898206 C,0,-1.6185986932,1.1722263078,0.000087606 C,0,-0.2279433474,1.2210775389,-0.0000638556 C,0,0.4719470027,0.00504704,-0.000205722 N,0,-0.1260145559,-1.1887418007,-0.0000265551 H,0,0.2962245523,2.1711585949,-0.0000746314 S,0,2.2587906746,-0.0954156481,-0.0001504586 H,0,2.4971496085,1.2321258605,0.0008428139 H,0,-1.9189912402,-2.2025372425,0.0002493858 H,0,-3.3416730236,-0.1474842482,0.0003104645 H,0,-2.1939847858,2.0939236505,0.0001541736 -------------------------------------------------- -------------------------------------------------- Thioamide 3 gas-phase -------------------------------------------------- B3LYP/6-31G(d) C,0,-1.424846,1.102320,-0.000374 C,0,-2.339126,0.088268,-0.000223 C,0,-1.855894,-1.244920,0.000292 C,0,-0.506956,-1.480980,0.000357 C,0, 0.462389,-0.424257,-0.000004 N,0,-0.076153,0.868251,-0.000361 S,0,2.125149,-0.696223,-0.000268 C,0,0.843903,2.010156,0.000620 H,0,-0.110519,-2.489260,0.000901 H,0,-1.716453,2.146066,-0.000695 H,0,-3.398402,0.316002,-0.000698 H,0,-2.554918,-2.076761,0.000723 H,0,1.487123,1.964412,0.882617 H,0,0.259767,2.932092,0.001237 H,0,1.487268,1.965727,-0.881268 B3LYP/6-311+G(2d,p) C,0,-1.4200635696,1.0978417705,-0.0000794053 C,0,-2.3301461654,0.0876021399,-0.0000430222 C,0,-1.8478678811,-1.2419191441,-0.0000272386 C,0,-0.5050070024,-1.4777940784,0.0001220431 C,0,0.4598407182,-0.4226159709,0.000673962 N,0,-0.0752495829,0.8659966196,0.0001592147 S,0,2.1175909265,-0.6954624525,-0.0002091129 C,0,0.8400944215,2.0085715987,-0.0000767067 H,0,-0.1104389745,-2.4836799548,-0.0000517473 H,0,-1.7135304088,2.1379983306,-0.0003024696 H,0,-3.3864487583,0.3143914834,-0.0002343401 H,0,-2.5449007552,-2.0715628226,-0.0002185174 H,0,1.4824176533,1.9667306051,0.8790429387 H,0,0.2542641479,2.9253414257,-0.0005539563 H,0,1.4828262239,1.9660859406,-0.878868399 HF/6-311+G(2d,p) C,0,-1.4110741532,1.0816537442,-0.0001347886 C,0,-2.3130783868,0.0913572595,-0.0001223571 C,0,-1.826117619,-1.241306302,-0.0000407873 C,0,-0.5015227622,-1.4723807861,0.0000624515 C,0,0.4504935482,-0.4021642131,0.0001904948 N,0,-0.0693934096,0.8534778162,-0.0000146173 S,0,2.1024073575,-0.6941175185,0.0001016218 C,0,0.8302179894,2.0050224133,-0.0000824347 H,0,-0.1022010118,-2.4652178235,0.0000855853 H,0,-1.7035484628,2.1115794822,-0.0002473339 H,0,-3.3606869499,0.3143670232,-0.0002200333 H,0,-2.5166475363,-2.0645490791,-0.000080009 H,0,1.460810287,1.9786935984,0.8751992975 H,0,0.2348839056,2.9052198646,-0.0003640885 H,0,1.4611142181,1.9783498219,-0.8751325178 MP2(full)/6-311+G(2d,p) C,0,1.411844,1.108682,-0.000092 C,0,2.330984,0.097484,-0.000112 C,0,1.859849,-1.231318,0.000042 C,0,0.511154,-1.470714,0.000142 C,0,-0.461762,-0.425402,0.000054 N,0,0.072654,0.859495,0.000060 S,0,-2.110941,-0.693705,-0.000103 C,0,-0.855750,1.983967,0.000113 H,0,0.122749,-2.481546,0.000273 H,0,1.695115,2.153645,-0.000150 H,0,3.385985,0.337696,-0.000299 H,0,2.558111,-2.061634,0.000115 H,0,-1.495722,1.925023,0.880136 H,0,-1.495718,1.925122,-0.879914 H,0,-0.281956,2.908318,0.000184 -------------------------------------------------- Thioimidate 4a gas-phase -------------------------------------------------- B3LYP/6-31G(d) C,0,1.528175,1.368975,-0.000159 C,0,2.560638,0.437416,0.000282 C,0,2.218114,-0.919519,0.000228 C,0,0.878165,-1.279943,0.000076 C,0,-0.086156,-0.255290,-0.000310 N,0,0.226591,1.041424,-0.000609 H,0,0.574008,-2.322434,0.000317 S,0,-1.806937,-0.727385,-0.000229 C,0,-2.627073,0.901977,0.000606 H,0,1.743893,2.436199,-0.000229 H,0,3.596663,0.760871,0.000602 H,0,2.989194,-1.685459,0.000581 H,0,-2.353747,1.471337,0.890282 H,0,-3.700351,0.695108,0.002047 H,0,-2.355988,1.470880,-0.890004 B3LYP/6-311+G(2d,p) C,0,1.5344169187,1.3644007405,-0.0000069783 C,0,2.5569636234,0.4303780879,0.0000048121 C,0,2.2081962828,-0.9207801294,0.0000097578 C,0,0.8725849056,-1.2724056771,0.0000018474 C,0,-0.0860044488,-0.2474498927,-0.0000045735 N,0,0.234770403,1.0415107368,-0.000010413 H,0,0.5647289907,-2.3107052684,0.0000010928 S,0,-1.7996924284,-0.7219630576,-0.0000077132 C,0,-2.6347296603,0.8948581805,0.0000160205 H,0,1.7556496516,2.4272393428,-0.0000106702 H,0,3.5918031341,0.7472104719,0.0000070876 H,0,2.9730926485,-1.688505863,0.0000151439 H,0,-2.3706154692,1.4610059663,-0.8898439977 H,0,-2.3706449451,1.4609661136,0.8899094892 H,0,-3.7008937065,0.6696151422,-0.0000071589 HF/6-311+G(2d,p) C,0,1.5230050896,1.3525989481,-0.0000022361 C,0,2.5431178068,0.4334874162,-0.0000029295 C,0,2.1975583655,-0.9108493573,-0.0000017793 C,0,0.872855552,-1.262232316,-0.0000009714 C,0,-0.0785663377,-0.2429289366,-0.0000004778 N,0,0.2386370327,1.0270535443,-0.0000015547 H,0,0.5671192443,-2.290892621,-0.0000005697 S,0,-1.7855801535,-0.7144390584,0.0000008572 C,0,-2.6359861329,0.8812794253,0.0000062552 H,0,1.7380700219,2.4062274515,-0.0000035152 H,0,3.5675762143,0.7518583849,-0.000004261 H,0,2.9575769186,-1.6708758829,-0.000002179 H,0,-2.3858954981,1.4464679764,-0.8836616449 H,0,-2.3859240586,1.4464457227,0.8836962394 H,0,-3.6916056756,0.6442880141,-0.0000140686 MP2(full)/6-311+G(2d,p) C,0,-1.522530,1.365017,-0.000002 C,0,-2.546320,0.428004,-0.000004 C,0,-2.202845,-0.924568,-0.000009 C,0,-0.863080,-1.274115,0.000006 C,0,0.098335,-0.254361,0.000025 N,0,-0.217383,1.042732,0.000007 H,0,-0.553799,-2.314081,0.000003 S,0,1.801637,-0.724995,-0.000005 C,0,2.583639,0.906688,-0.000005 H,0,-1.743409,2.428527,-0.000005 H,0,-3.581608,0.748630,-0.000010 H,0,-2.968366,-1.693314,-0.000015 H,0,2.301173,1.465337,0.888646 H,0,2.301018,1.465421,-0.888554 H,0,3.657287,0.720281,-0.000110 -------------------------------------------------- Thioimidate 4b gas-phase -------------------------------------------------- B3LYP/6-31G(d) C,0,2.0699573612,-1.0107111768,-0.0000085557 C,0,2.6130259504,0.2745174955,-0.0000177577 C,0,1.728692721,1.352648169,0.0000345387 C,0,0.3561767534,1.1138301393,0.0000261407 C,0,-0.0816503862,-0.2194219478,-0.0000604983 N,0,0.7583525953,-1.2624900644,0.000004254 H,0,-0.3434884829,1.9411821059,0.0001423624 S,0,-1.7902729251,-0.728806005,0.00003548 C,0,-2.7005381757,0.8523936647,-0.0000532392 H,0,2.71806407,-1.8857403629,0.0000080826 H,0,3.688435594,0.4208246327,-0.0001282242 H,0,2.1000958334,2.3742717154,0.0000495965 H,0,-2.4911397901,1.4426628676,0.8965702065 H,0,-3.7597463941,0.5825041225,-0.0005775343 H,0,-2.4903075414,1.4430833863,-0.8961857173 B3LYP/6-311+G(2d,p) C,0,2.0669288565,-1.0070225352,0.0000365914 C,0,2.6055881395,0.2746854182,0.0001253191 C,0,1.7230165054,1.3480884211,0.0001404743 C,0,0.3562859557,1.1090666653,0.0000582149 C,0,-0.0816927918,-0.21935726,-0.0000591481 N,0,0.7588408013,-1.2560556856,-0.000054712 H,0,-0.3408061564,1.9343858573,0.0000859489 S,0,-1.7844903939,-0.7258885788,-0.0001250357 C,0,-2.6985924928,0.84877899,-0.0000015759 H,0,2.7146437807,-1.8785027522,0.0000206007 H,0,3.6777716845,0.4218419456,0.0001887411 H,0,2.0925053024,2.3670863129,0.0002228188 H,0,-2.4908177882,1.433596864,0.8956820463 H,0,-3.7516532191,0.569070789,0.0000245717 H,0,-2.4908879459,1.433689848,-0.8956404265 HF/6-311+G(2d,p) C,0,-2.049102,-1.000470,0.000056 C,0,-2.593806,0.267980,-0.000049 C,0,-1.719127,1.335454,-0.000131 C,0,-0.360208,1.101671,-0.000118 C,0,0.074815,-0.216029,-0.000046 N,0,-0.755117,-1.238276,0.000056 H,0,0.328817,1.920417,-0.000165 S,0,1.773193,-0.717762,0.000049 C,0,2.695490,0.837440,0.000093 H,0,-2.686537,-1.866840,0.000119 H,0,-3.657382,0.408268,-0.000057 H,0,-2.088129,2.345117,-0.000199 H,0,2.495757,1.419591,-0.888451 H,0,3.738077,0.549756,0.000085 H,0,2.495759,1.419544,0.888668 MP2(full)/6-311+G(2d,p) C,0,2.062856,-1.007963,0.000003 C,0,2.594014,0.278865,0.000076 C,0,1.709012,1.351515,0.000106 C,0,0.341256,1.102208,0.000062 C,0,-0.095028,-0.225924,-0.000015 C,0,0.750653,-1.266814,-0.000043 H,0,-0.359829,1.926314,0.000088 S,0,-1.787043,-0.729257,-0.000077 C,0,-2.647075,0.863894,-0.000024 H,0,2.714514,-1.877052,-0.000023 H,0,3.667267,0.429687,0.000108 H,0,2.073362,2.373566,0.000165 H,0,-2.418777,1.441188,0.895054 H,0,-3.710050,0.625200,-0.000162 H,0,-2.418582,1.441349,-0.894949 -------------------------------------------------- -------------------------------------------------- Thioamide 3 liquid-phase SCRF=SCIPCM -------------------------------------------------- B3LYP/6-31G(d) Dielectric=2.28 C,0,1.4253143881,1.100539872,0.000056875 C,0,2.3387835627,0.0841954127,0.0001897965 C,0,1.8556755078,-1.2466183487,0.0000677389 C,0,0.50453216,-1.4808299915,-0.0000880442 C,0,-0.4585894558,-0.4225248639,0.0000611495 N,0,0.0767686483,0.8668925697,0.0001211066 S,0,-2.1291660727,-0.6956297179,-0.0001985693 C,0,-0.8388306322,2.0145126998,0.000049887 H,0,0.1090766892,-2.4893560774,-0.0001443502 H,0,1.7177318695,2.1434809434,0.0001272575 H,0,3.3980601187,0.3110493514,0.0002140676 H,0,2.5528693221,-2.0795980277,0.0000690315 H,0,-1.4798503053,1.9738085672,-0.8831706344 H,0,-0.2503767579,2.9325763915,-0.0003001496 H,0,-1.4795474944,1.974217668,0.8835097255 -------------------------------------------------- Thioamide 3 liquid-phase SCRF=Onsager A0=4.45 -------------------------------------------------- B3LYP/6-31G(d) Dielectric=2.28 C,0,-1.4264494486,1.1004590356,-0.0001094791 C,0,-2.3398499216,0.0851807398,-0.0000438783 C,0,-1.8552886281,-1.2459969836,0.0000202008 C,0,-0.5050791327,-1.4805737638,0.0000747505 C,0,0.4611046371,-0.4233579899,0.0001387267 N,0,-0.0772177746,0.8668775325,0.0000828357 S,0,2.1286074717,-0.6943065947,-0.0000852705 C,0,0.8397141303,2.0115717365,0.0000665672 H,0,-0.1077886894,-2.4884835756,0.0000860381 H,0,-1.719659305,2.1435603708,-0.0002130585 H,0,-3.3992286942,0.3117262234,-0.0001875701 H,0,-2.5540469754,-2.0779690047,0.0000228525 H,0,1.4825390324,1.9681308161,0.88236553 H,0,0.2536309747,2.9318728931,0.0001439211 H,0,1.4824487144,1.9682284165,-0.8823145623 -------------------------------------------------- Thioimidate 4a liquid-phase SCRF=SCIPCM -------------------------------------------------- B3LYP/6-31G(d) Dielectric=2.28 C,0,1.5309578086,1.3694629815,-0.0000071736 C,0,2.5624690437,0.4366988329,-0.0000189291 C,0,2.2190862401,-0.9201041009,0.0000000664 C,0,0.8784467941,-1.2796205487,0.000005013 C,0,-0.08463,-0.2541238232,0.0000681234 N,0,0.2282505601,1.0427307684,0.0000032435 H,0,0.5744302832,-2.3220813968,0.0000301139 S,0,-1.806932036,-0.7266001913,-0.0000095374 C,0,-2.6335210379,0.899760487,0.0000123209 H,0,1.7483930655,2.4361910439,-0.0000211008 H,0,3.5986123438,0.7592805526,-0.000016319 H,0,2.9893352379,-1.6865515286,-0.0000247875 H,0,-2.3680318151,1.4676304131,0.8929015319 H,0,-3.7056615789,0.6882162895,-0.0047985055 H,0,-2.3607719729,1.4713593369,-0.8882975655 -------------------------------------------------- Thioimidate 4a liquid-phase SCRF=Onsager A0=4.32 -------------------------------------------------- B3LYP/6-31G(d) Dielectric=2.28 C,0,-1.5270495825,1.3691064979,-0.0000488424 C,0,-2.5599407752,0.4380062753,0.0000684304 C,0,-2.2182874421,-0.9190592305,0.0000798729 C,0,-0.878431259,-1.2803602247,0.0000196758 C,0,0.0859633797,-0.2561276565,-0.0001375218 N,0,-0.2255873308,1.0406280358,-0.0001384942 H,0,-0.5749673231,-2.3230710704,0.0000733031 S,0,1.8073764453,-0.7277669054,-0.0000575615 C,0,2.6248357177,0.9029715083,0.0001716354 H,0,-1.7423145461,2.4363572785,-0.0000683176 H,0,-3.5957277553,0.7619484335,0.0001339205 H,0,-2.9899090395,-1.6843741848,0.0002198281 H,0,2.3517786537,1.4717069277,-0.8899833071 H,0,3.6985901,0.6981738245,0.0006029778 H,0,2.3510978691,1.4719100084,0.8899925368 -------------------------------------------------- Thioimidate 4b liquid-phase SCRF=Onsager A0=4.19 -------------------------------------------------- B3LYP/6-31G(d) Dielectric=2.28 C,0,-2.0709899614,-1.0096432175,0.0001096367 C,0,-2.6127915224,0.2756732483,0.0000593712 C,0,-1.7276734103,1.3533528488,-0.0000747698 C,0,-0.3555078803,1.1126502797,-0.0001265211 C,0,0.0807638769,-0.2208426248,-0.0000243499 N,0,-0.7593189108,-1.263992032,0.0000540418 H,0,0.3444725217,1.9395640167,-0.0002726419 S,0,1.7908440311,-0.7289357867,-0.0001408624 C,0,2.7003112536,0.8530457817,0.000238547 H,0,-2.7207589611,-1.8836575795,0.0002032678 H,0,-3.6879491462,0.4234908543,0.0001091297 H,0,-2.0978489562,2.3752072684,-0.0001375375 H,0,2.4890484179,1.4436878633,-0.8954939825 H,0,3.7598510293,0.5846452302,-0.0006163582 H,0,2.490238836,1.4425612599,0.8969921436 Copyright The Royal Society of Chemistry, 1999