Comment on the Correct Use of Continuum Solvent Models Junming Ho a, Andreas Klamt b,c and Michelle L. Coote 1,a a ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra ACT 0200, Australia b COSMOlogic GmbH&CoKG, Burscheider Str. 515, 51381 Leverkusen, Germany c Institute of Physical and Theoretical Chemistry, University of Regensburg, 93040 Regensburg, Germany SUPPPORTING INFORMATION 1 Correspondence author. Email: mcoote@rsc.anu.edu.au S1
Table S1. B3LYP/6-31+G(d) thermal corrections (Hartrees) to the free energy of the solute obtained in the gas and solution phase (CPCM-UAKS) based on the harmonic oscillator rigid rotor approximation. Acid Gcorr,gas Gcorr,aq Δ (kcal mol -1 ) Conjugate base Gcorr,gas Gcorr,aq Δ (kcal mol -1 ) ch3oh 0.028544 0.027739 0.5 ch3oh 0.013917 0.016224 1.4 ch3ch2oh 0.054605 0.05366 0.6 ch3ch2oh 0.039452 0.041253 1.1 phenol 0.075462 0.074373 0.7 phenol 0.061612 0.062491 0.6 hcooh 0.009604 0.008435 0.7 hcooh -0.003736-0.003303 0.3 ch3cooh 0.034562 0.032997 1.0 ch3cooh 0.020099 0.022613 1.6 cf3cooh 0.007054 0.006274 0.5 cf3cooh -0.00665-0.005512 0.7 hf -0.007474-0.008532 0.7 hf -0.014159-0.014159 0.0 hcl -0.011219-0.01144 0.1 hcl -0.015023-0.015023 0.0 hooh 0.003953 0.00248 0.9 hooh -0.008885-0.010114 0.8 hocl -0.010026-0.010875 0.5 hocl -0.019916-0.019781 0.1 hno2-0.003865-0.004777 0.6 hno2-0.015823-0.01589 0.0 h2so4 0.00959 0.007165 1.5 h2so4-0.002707-0.003347 0.4 ch3coch3 0.055421 0.054994 0.3 ch3coch3 0.043688 0.044279 0.4 hcn -0.003046-0.003139 0.1 hcn -0.014213-0.014085 0.1 ch3cooch2ch3 0.085937 0.084692 0.8 ch3cooch2ch3 0.070886 0.072058 0.7 4f-phenol 0.065807 0.064513 0.8 4f-phenol 0.052131 0.052739 0.4 hno3 0.000415-0.000859 0.8 hno3-0.011619-0.011783 0.1 hn3-0.001688-0.003139 0.9 hn3-0.010526-0.010562 0.0 pyruvic 0.041229 0.039661 1.0 pyruvic 0.026762 0.026923 0.1 cf3ch2oh 0.027652 0.026155 0.9 cf3ch2oh 0.012678 0.013305 0.4 4no2-phenol 0.073955 0.072649 0.8 4no2-phenol 0.061177 0.061028 0.1 ch2(cn)2 0.016985 0.016636 0.2 ch2(cn)2 0.00395 0.004055 0.1 ch3ch2cn 0.04788 0.047554 0.2 ch3ch2cn 0.031869 0.032024 0.1 ch3so3h 0.03199 0.031415 0.4 ch3so3h 0.021587 0.02154 0.0 (cf3)2coh 0.026201 0.024333 1.2 (cf3)2coh 0.011378 0.010791 0.4 2-propanol 0.08065 0.079699 0.6 2-propanol 0.065585 0.067085 0.9 (ch3)3coh 0.106758 0.10599 0.5 (ch3)3coh 0.092917 0.093538 0.4 MAD 0.7 MAD 0.4 S2
Table S2. The experimental and calculated solvation free energies a (kcal mol -1 ) of 50 neutral and ionic solutes. Expt PCM-UAHF b ΔG solv PCM-UAHF (HF/6-31+G*) MP2 (PCM-UAHF) PCM-UAHF (MP2/6-311+G(3df,2p) c MP2 (Gas) PCM-UAHF (HF/6-31+G*) d ΔG solv = E soln + G nes - G gas PCM-UAHF (HF/6-31+G*) e ΔG solv = G soln (Freq)-G gas ΔG nes ΔG solv E soln + G nes G gas ΔG solv G soln (Freq) ΔG solv c5h5n -4.7-5.2-247.761720-247.753747 0.61-4.4-246.711713-246.634802-50.2-246.644551-6.1 c6h6-0.9 1.9-231.724155-231.720224 4.85 2.4-230.70804-230.62851-51.8-230.633612-3.2 ch2ch2 1.3 1.3-78.394428-78.393186 2.2 1.4-78.03377-78.001971-21.8-78.003608-1.0 ch3ch3 1.8 2.0-79.620490-79.620258 2.06 1.9-79.226345-79.171283-36.4-79.171637-0.2 ch3cho -3.5-4.4-153.543626-153.537371 1.16-2.8-152.928126-152.886229-28.2-152.895473-5.8 ch3cl -0.6-0.7-499.510557-499.507767 1.55-0.2-499.095246-499.076097-13.9-499.079887-2.4 ch3cn -3.9-4.0-132.491524-132.483317 2.01-3.1-131.937529-131.905284-22.1-131.91609-6.8 ch3coch3-3.8-4.4-192.774334-192.767542 1.35-2.9-191.974631-191.905819-45.1-191.916517-6.7 ch3conh2-9.7-10.5-208.847592-208.832252 0.89-8.7-208.000743-207.933278-44.2-207.952661-12.2 ch3cooch3-3.3-3.9-267.908917-267.902251 1.42-2.8-266.850071-266.776206-48.2-266.785488-5.8 ch3cooh-base -77.0-75.5-228.252540-228.138808 0.68-70.7-227.369772-227.225821-92.2-227.34943-77.6 ch3cooh -6.7-7.8-228.711708-228.699704 1.2-6.3-227.830346-227.778102-34.7-227.794374-10.2 ch3f -0.2-0.6-139.527993-139.525010 1.82-0.1-139.045201-139.023273-15.7-139.0274-2.6 ch3nh2-4.6-5.3-95.659496-95.652132-0.17-4.8-95.222619-95.168226-36.0-95.177294-5.7 ch3och3-1.9-2.5-154.721233-154.717104 0.57-2.0-154.073439-154.008139-42.9-154.013405-3.3 ch3oh-base -95.0-87.9-115.025525-114.893925-0.13-82.7-114.551176-114.393707-100.7-114.534158-88.1 ch3oh -5.1-5.8-115.522133-115.513439 0.51-4.9-115.050251-115.008461-28.1-115.019498-6.9 ch3sh -1.2-1.5-438.110202-438.106966 0.89-1.1-437.703669-437.675905-19.3-437.679915-2.5 ch4 2.0 1.1-40.406026-40.405694 1.28 1.1-40.193888-40.165298-19.8-40.165791-0.3 chch-base -76.1-73.2-76.664947-76.545953 1.47-73.2-76.32675-76.213726-72.8-76.332373-74.5 chch 0.0-0.1-77.159501-77.155919 2.65 0.4-76.823167-76.812533-8.6-76.817171-2.9 h+ch3coch3-64.0-69.2-193.193610-193.082863 0.67-68.8-192.400106-192.214462-118.4 - f - f h+ch3nh2-70.0-70.8-96.118110-96.005451-0.25-70.9-95.687015-95.512192-111.6-95.626227-71.6 h+ch3och3-70.0-72.2-155.144474-155.026653 1.15-72.8-154.499048-154.310542-120.2 - f - f h+ch3oh -85.0-89.9-115.954242-115.808716 0.62-90.7-115.483968-115.295327-120.3-115.456773-101.3 h+ch3sh -74.0-76.5-438.532029-438.407758 1.34-76.6-438.123687-437.964974-101.5 - f - f h+h2o -104.0-106.7-7.68E+01-76.588983-0.24-106.6-76.460705-76.272955-119.7-76.45164-112.1 h+h2s -87.0-87.4-399.305305-399.168470-1.39-87.3-399.081977-398.934753-94.3-399.077455-89.5 h+me3n -59.0-59.5-174.542643-174.447262 0.39-59.5-173.746384-173.532133-136.3-173.628977-60.8 S3
h+nh3-79.0-80.1-56.913344-56.786036-0.43-80.3-56.658877-56.497625-103.1-56.626408-80.8 h+phnh2-66.0-65.3-287.434176-287.330130 0.73-64.6-286.197019-285.981913-136.9-286.088907-67.1 h2co -1.7-2.4-114.310008-114.305394 2-0.9-113.875002-113.862968-9.4-113.870059-4.4 h2o-base -106.0-105.4-75.848482-75.688236 1.14-99.4-75.544328-75.383608-102.7 - f - f h2o -6.3-7.2-76.328422-76.317983 0.69-5.9-76.029169-76.013078-12.0-76.026619-8.5 h2s-base -74.0-70.3-398.438595-398.329304-0.53-69.1-398.218993-398.118393-65.0-398.22992-70.0 h2s -0.4-0.4-398.895534-398.893087 1.44-0.1-398.668818-398.671847 0.0-398.674973-2.0 hcn-base -67.6-72.1-92.799041-92.685561 1.38-69.8-92.429818-92.328581-65.4-92.445662-73.5 hcn -3.2-3.3-93.258320-93.250873 2.34-2.3-92.883952-92.880067-4.3-92.889301-5.8 hcooh-base -76.2-74.4-189.027842-188.914768 0.62-70.3-188.326765-188.209713-75.3-188.329877-75.4 hcooh -7.0-8.3-189.481976-189.469593 1.09-6.7-188.782409-188.756337-18.3-188.772987-10.4 me3n -3.2-3.2-174.079423-174.074954-0.29-3.1-173.277938-173.169802-69.8 - f - f nh3-4.3-4.8-56.457314-56.450442 0.36-4.0-56.197199-56.171557-18.0-56.180529-5.6 phcho -4.0-4.7-344.872824-344.865126 2.1-2.7-343.451366-343.356218-61.6-343.367694-7.2 phcl -1.1-1.7-690.838511-690.833752 1.89-1.1-689.612796-689.541458-46.7-689.547701-3.9 phnh2-4.9-5.4-286.995004-286.985649 1.25-4.6-285.749674-285.644615-67.8-285.655928-7.1 phno2-4.1-4.3-435.949869-435.942223 2.43-2.4-434.194879-434.108238-56.3-434.120009-7.4 phoh-base -72.0-66.9-306.383238-306.282670 0.88-62.2-305.101972-304.926131-112.2-305.036165-69.0 phoh -6.6-7.6-306.858251-306.846061 1.08-6.6-305.58048-305.485144-61.7-305.500248-9.5 phsh-base -67.0-62.3-628.983420-628.888862 0.56-58.8-627.767538-627.600974-106.4 - e phsh -2.6-2.0-629.436878-629.431898 1.62-1.5-628.221078-628.141735-51.7-628.149021-4.6 MAD 1.4 MAD 2.0 MAD 29.5 MAD 2.9 AD max 7.1 AD max 12.3 AD max 77.3 AD max 16.3 a Experimental values are adopted from reference 17, and all solvation free energies refer to a standard state of 1 mol L -1 in both gas and solution phase. b PCM-UAHF solvation free energies computed at the HF/6-31+G* level on corresponding gas phase optimised geometries (in accordance with parameterisation) c PCM-UAHF solvation free energies but with the electrostatic component computed at the MP2/6-311+G(3df,2p) level of theory. d Manual calculation of solvation free energies by using PCM-UAHF/HF/6-31+G* E soln + G nes (assumed to have a standard state of 1 mol L -1 ) in place of G soln in equation (2). G gas is obtained via a frequency calculation at the HF/6-31+G* level. e Manual calculation of solvation free energies by using PCM-UAHF/HF/6-31+G* G soln obtained from a frequency calculation on the solution optimised geometry. G gas is obtained via a frequency calculation at the HF/6-31+G* level. f Convergence problems during geometry optimisation in solution. S4
Table S3. Complete references 8 and 9. (8) Frisch, M. J.; G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A. Gaussian 03, Revision E.01 Gaussian, Inc., Wallingford CT, 2004. (9) Higashi, M.; M., A. V.; Olson, R. M.; Chamberlin, A. C.; Pu, J.; Kelly, C. P.; Thompson, J. ; D.; Xidos, J. D. L., J.; Zhu, T.; Hawkins, G. D.; Chuang, Y.-Y.; Fast, P. L.; Lynch, B. J.; Liotard, ; D. A.; Rinaldi, D. G., J.; Cramer, C. J.; Truhlar, D. G. GAMESSPLUS version 2008 2, ; University of Minnesota, M., 2008, based on the General Atomic and Molecular ; Electronic Structure System (GAMESS) as described in Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comp. Chem. 1993, 14, 1347. S5
Table S4. The gas phase geometries of all the species appearing in Table S2. NOTE: All species had zero imaginary frequencies, as determined from frequency calculations at the HF/6-31+G(d) level. c5h5n 1\1\GINC-X101\FOpt\RHF\6-31+G(d)\C5H5N1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\n,0.032528 0142,0.,0.0187800578\C,0.0579981766,0.,1.3406039725\C,1.2287200747,0., 2.0849123798\C,2.4367101753,0.,1.4068352757\C,2.4199471229,0.,0.021646 609\C,1.1899961849,0.,-0.620074092\H,-0.8987213339,0.,1.8325875662\H,1.1891133102,0.,3.158720282\H,3.3682413406,0.,1.9446550447\H,3.33008866 28,0.,-0.5495578064\H,1.13770672,0.,-1.6946092891\\Version=EM64L-G03Re ve.01\state=1-a1\hf=-246.7034909\rmsd=5.627e-09\rmsf=9.880e-05\thermal =0.\Dipole=0.8187041,0.,0.472679\PG=C02V [C2(H1C1N1),SGV(C4H4)]\\@ c6h6 1\1\GINC-X126\FOpt\RHF\6-31+G(d)\C6H6\JMH502\09-Jul-2010\0\\# HF/6-31+ G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.01020285 73,0.,0.0058906224\C,0.0102028573,0.,1.3941093776\C,1.2124355653,0.,2. 0882187551\C,2.4146682733,0.,1.3941093776\C,2.4146682733,0.,0.00589062 24\C,1.2124355653,0.,-0.6882187551\H,-0.9212403641,0.,1.9318783722\H,1.2124355653,0.,3.1637567444\H,3.3461114947,0.,1.9318783722\H,3.3461114 947,0.,-0.5318783722\H,1.2124355653,0.,-1.7637567444\H,-0.9212403641,0.,-0.5318783722\\Version=EM64L-G03RevE.01\State=1-A1G\HF=-230.7110924\ RMSD=8.088e-09\RMSF=8.834e-05\Thermal=0.\Dipole=0.,0.,0.\PG=D06H [3C2' (H1C1.C1H1)]\\@ ch2ch2 1\1\GINC-X126\FOpt\RHF\6-31+G(d)\C2H4\JMH502\09-Jul-2010\0\\# HF/6-31+ G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.,0.,0.00 70105128\C,0.,0.,1.3279894872\H,0.9151869097,0.,-0.5589300608\H,0.9151 869097,0.,1.8939300608\H,-0.9151869097,0.,1.8939300608\H,-0.9151869097,0.,-0.5589300608\\Version=EM64L-G03RevE.01\State=1-AG\HF=-78.0358172\ RMSD=6.856e-09\RMSF=5.281e-05\Thermal=0.\Dipole=0.,0.,0.\PG=D02H [C2"( C1.C1),SG(H4)]\\@ ch3ch3 1\1\GINC-X127\FOpt\RHF\6-31+G(d)\C2H6\JMH502\09-Jul-2010\0\\# HF/6-31+ G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.01826057 36,-0.0316282413,0.0129121754\H,0.0348054199,-0.0602847556,1.098266529 6\H,1.0470574208,-0.0602847556,-0.3332739786\H,-0.4713205806,-0.936920 7035,-0.3332739786\C,-0.7017971288,1.2155482836,-0.4962455088\H,-0.718 341975,1.244204798,-1.581599863\H,-1.730593976,1.244204798,-0.15005935 47\H,-0.2122159746,2.1208407458,-0.1500593547\\Version=EM64L-G03RevE.0 1\State=1-A1G\HF=-79.2294502\RMSD=8.358e-09\RMSF=5.977e-05\Thermal=0.\ Dipole=0.,0.,0.\PG=D03D [C3(C1.C1),3SGD(H2)]\\@ ch3cho 1\1\GINC-X101\FOpt\RHF\6-31+G(d)\C2H4O1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.010327 0517,-0.0008286168,0.0072454067\O,-0.0185773894,-0.0017079826,1.196299 9192\C,1.2697004834,0.0123862801,-0.8127938908\H,-0.9249763892,-0.0097 437969,-0.5615056752\H,1.2912143465,-0.8573265108,-1.4641469589\H,1.28 02403943,0.8922154649,-1.4508276962\H,2.1412924435,0.0133933935,-0.172 1850494\\Version=EM64L-G03RevE.01\State=1-A\HF=-152.9211208\RMSD=7.632 e-09\rmsf=4.216e-05\thermal=0.\dipole=0.1963147,0.0031314,-1.2524648\p G=C01 [X(C2H4O1)]\\@ ch3cl 1\1\GINC-X128\FOpt\RHF\6-31+G(d)\C1H3Cl1\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.07204 90448,0.1247926063,0.0509463682\H,0.0620689738,0.1075066162,1.12859201 93\H,1.084736418,0.1075066162,-0.3176781501\Cl,-0.7695896885,-1.332968 4415,-0.5441820875\H,-0.4492647483,0.9931626025,-0.3176781501\\Version =EM64L-G03RevE.01\State=1-A1\HF=-499.094158\RMSD=8.629e-09\RMSF=7.097e S6
-05\Thermal=0.\Dipole=0.4292588,0.743498,0.3035318\PG=C03V [C3(C1Cl1), 3SGV(H1)]\\@ ch3cn 1\1\GINC-X134\FOpt\RHF\6-31+G(d)\C2H3N1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.,0.,-0.074651377\c,0.,0.,1.3943403208\n,0.,0.,2.5298111672\h,-1.0184349262,0.,-0.4401667057\h,0.5092174631,0.8819905182,-0.4401667057\h,0.50921746 31,-0.8819905182,-0.4401667057\\Version=EM64L-G03RevE.01\State=1-A1\HF =-131.9311733\RMSD=6.106e-09\RMSF=4.143e-05\Thermal=0.\Dipole=0.,0.,-1.6535102\PG=C03V [C3(C1C1N1),3SGV(H1)]\\@ ch3coch3 1\1\GINC-X136\FOpt\RHF\6-31+G(d)\C3H6O1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.,0.,0. 0713241514\O,0.,0.,1.2653692978\C,1.2884715585,0.,-0.7220261657\C,-1.2 884715585,0.,-0.7220261657\H,1.3336706232,0.8743496316,-1.3651863851\H,2.1357090857,0.,-0.0504477887\H,1.3336706232,-0.8743496316,-1.3651863 851\H,-1.3336706232,-0.8743496316,-1.3651863851\H,-2.1357090857,0.,-0. 0504477887\H,-1.3336706232,0.8743496316,-1.3651863851\\Version=EM64L-G 03RevE.01\State=1-A1\HF=-191.9676127\RMSD=5.348e-09\RMSF=4.817e-05\The rmal=0.\dipole=0.,0.,-1.32832\pg=c02v [C2(C1O1),SGV(C2H2),X(H4)]\\@ ch3conh2 1\1\GINC-X100\FOpt\RHF\6-31+G(d)\C2H5N1O1\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\n,-0.005 9892182,-0.0107321204,-0.0045225311\C,0.0075468362,0.0559322985,1.3490 153407\C,1.3754237626,0.0187808031,1.9940565282\O,-1.0032843367,0.1195 01672,1.9934416281\H,-0.8853290154,-0.0575259148,-0.4696245923\H,0.822 0662193,-0.1080488655,-0.5439693677\H,2.1414426699,0.4659298017,1.3706 839518\H,1.6457428391,-1.0161471308,2.1800374601\H,1.3299504679,0.5344 920369,2.9425174767\\Version=EM64L-G03RevE.01\State=1-A\HF=-207.983986 9\RMSD=5.966e-09\RMSF=3.472e-06\Thermal=0.\Dipole=1.2670015,-0.1819879,-1.0898381\PG=C01 [X(C2H5N1O1)]\\@ ch3cooch3 1\1\GINC-X137\FOpt\RHF\6-31+G(d)\C3H6O2\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.008369 9581,-0.0144971927,-0.0238201809\H,0.0776671448,-0.1345234409,1.047121 9744\H,1.0007221883,0.0171405448,-0.4588241597\H,-0.5152052414,-0.8580 805648,-0.4588241597\C,-0.7264391001,1.25822943,-0.3424933083\O,-0.834 5922072,1.4455561066,-1.6503290458\O,-1.1642235184,2.0164942852,0.4637 510614\C,-1.5084040279,2.6126324146,-2.0897321095\H,-1.4859001654,2.57 36545814,-3.1673673303\H,-2.5288769231,2.616553714,-1.7344594751\H,-1. 0015635252,3.4983485155,-1.7344594751\\Version=EM64L-G03RevE.01\State= 1-A'\HF=-266.8438821\RMSD=8.194e-09\RMSF=9.792e-05\Thermal=0.\Dipole=0.204048,-0.3534215,-0.7260592\PG=CS [SG(C3H2O2),X(H4)]\\@ ch3cooh-base 1\1\GINC-X101\FOpt\RHF\6-31+G(d)\C2H3O2(1-)\JMH502\09-Jul-2010\0\\# HF /6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\-1,1\c,0.0 043239874,0.0059833716,-0.0083680832\O,-0.0181303766,-0.0160856206,1.2 294916497\O,0.982900487,-0.0153578215,-0.7657679804\C,-1.3826067326,0. 0318059592,-0.6938078776\H,-1.7944033851,-0.976703115,-0.6866060195\H, -2.0712952483,0.6673442254,-0.1441184175\H,-1.3113402599,0.3637411376, -1.7248500552\\Version=EM64L-G03RevE.01\State=1-A\HF=-227.2495155\RMSD =5.220e-09\RMSF=6.333e-05\Thermal=0.\Dipole=-1.5323479,0.0424428,-0.76 52709\PG=C01 [X(C2H3O2)]\\@ ch3cooh 1\1\GINC-X138\FOpt\RHF\6-31+G(d)\C2H4O2\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,-0.00113 97487,0.0019741027,-0.0077576337\H,0.0242355707,-0.0419772398,1.070504 5392\H,1.0076689217,0.0052055068,-0.4045107387\H,-0.508342562,-0.87006 41314,-0.4045107387\C,-0.7193713061,1.2459876517,-0.4440710054\O,-0.77 89956652,1.349260071,-1.770649401\O,-1.191695624,2.0640773679,0.278064 2326\H,-1.241842394,2.1509341213,-1.995137255\\Version=EM64L-G03RevE.0 1\State=1-A'\HF=-227.8179204\RMSD=6.042e-09\RMSF=1.114e-04\Thermal=0.\ S7
Dipole=0.2990869,-0.5180338,-0.4771113\PG=CS [SG(C2H2O2),X(H2)]\\@ ch3f 1\1\GINC-X138\FOpt\RHF\6-31+G(d)\C1H3F1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.032325 5439,0.0559894844,0.0228576113\H,0.0231046688,0.0400184603,1.103398904 4\H,1.0479960198,0.0400184603,-0.3460163441\F,-0.614085227,-1.06362681 34,-0.4342238283\H,-0.4893410067,0.9276004064,-0.3460163441\\Version=E M64L-G03RevE.01\State=1-A1\HF=-139.0442267\RMSD=2.032e-09\RMSF=1.217e- 05\Thermal=0.\Dipole=0.405518,0.7023778,0.2867446\PG=C03V [C3(C1F1),3S GV(H1)]\\@ ch3nh2 1\1\GINC-X139\FOpt\RHF\6-31+G(d)\C1H5N1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,-0.00795 54661,0.0170766369,-0.0076445797\H,-0.0096217969,-0.0032972439,1.07584 47009\N,1.3662608997,0.0002448776,-0.4831961298\H,-0.5142243874,-0.877 2945683,-0.3513869534\H,-0.5874842877,0.8814123828,-0.3320455859\H,1.4 044160761,-0.0007649058,-1.4837218616\H,1.8700007325,0.8056513743,-0.1 668495905\\Version=EM64L-G03RevE.01\State=1-A'\HF=-95.2141731\RMSD=4.0 51e-09\RMSF=6.508e-05\Thermal=0.\Dipole=-0.2618327,0.5066995,-0.217717 \PG=CS [SG(C1H1N1),X(H4)]\\@ ch3och3 1\1\GINC-X140\FOpt\RHF\6-31+G(d)\C2H6O1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.009831 1864,0.0170281144,0.0172724222\H,-0.0301058755,-0.0521449059,1.0952434 723\H,1.0513110686,0.0520229991,-0.2977226379\O,-0.6367694917,-1.10291 71123,-0.4994719487\H,-0.4806022955,0.9364735922,-0.2977226379\C,-0.66 48315649,-1.1515220489,-1.8909620036\H,-1.1863043451,-2.054739399,-2.1 749796409\H,-1.1904570849,-0.2930309689,-2.3054951787\H,0.3414562793,- 1.1774815621,-2.3054951787\\Version=EM64L-G03RevE.01\State=1-A1\HF=-15 4.0694305\RMSD=4.443e-09\RMSF=8.703e-05\Thermal=0.\Dipole=0.2505449,0. 4339565,-0.354324\PG=C02V [C2(O1),SGV(C2H2),X(H4)]\\@ ch3oh-base 1\1\GINC-X140\FOpt\RHF\6-31+G(d)\C1H3O1(1-)\JMH502\09-Jul-2010\0\\# HF /6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\-1,1\o,0., 0.,-0.0108443391\C,0.,0.,1.3196468107\H,1.0159861468,0.,1.7933991761\H,-0.5079930734,0.8798698131,1.7933991761\H,-0.5079930734,-0.8798698131,1.7933991761\\Version=EM64L-G03RevE.01\State=1-A1\HF=-114.4111198\RMS D=9.406e-09\RMSF=7.305e-06\Thermal=0.\Dipole=0.,0.,1.1986654\PG=C03V [ C3(C1O1),3SGV(H1)]\\@ ch3oh 1\1\GINC-X141\FOpt\RHF\6-31+G(d)\C1H4O1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.002850 2309,0.0049367447,-0.0156119907\H,-0.0124416975,-0.0215496522,1.064418 6841\H,1.0369290514,0.0259299738,-0.3484277134\O,-0.6616145734,-1.1459 500561,-0.4616941613\H,-0.4960085096,0.9109718874,-0.3484277134\H,-0.6 762876375,-1.1713645487,-1.4075904384\\Version=EM64L-G03RevE.01\State= 1-A'\HF=-115.0409652\RMSD=2.854e-09\RMSF=6.152e-05\Thermal=0.\Dipole=0.319835,0.5539705,-0.4586648\PG=CS [SG(C1H2O1),X(H2)]\\@ ch3sh 1\1\GINC-X141\FOpt\RHF\6-31+G(d)\C1H4S1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.057155 7199,0.0989966107,0.0657516967\H,0.0706919,0.1224419624,1.1470434144\H,1.0765720163,0.0935000151,-0.2941260534\S,-0.8195489865,-1.419500484, -0.4130892739\H,-0.4573126198,0.9790887227,-0.2941260534\H,-0.73413115 84,-1.2715524657,-1.7287870528\\Version=EM64L-G03RevE.01\State=1-A'\HF =-437.7012965\RMSD=5.446e-09\RMSF=2.395e-05\Thermal=0.\Dipole=0.347692 1,0.6022204,-0.2020674\PG=CS [SG(C1H2S1),X(H2)]\\@ ch4 1\1\GINC-X128\FOpt\RHF\6-31+G(d)\C1H4\JMH502\09-Jul-2010\0\\# HF/6-31+ G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.,0.,0.\h,0.,0.,1.0834965872\h,1.0215303789,0.,-0.3611655291\h,-0.5107651895,-0 S8
.8846712589,-0.3611655291\H,-0.5107651895,0.8846712589,-0.3611655291\\ Version=EM64L-G03RevE.01\State=1-A1\HF=-40.1956672\RMSD=7.467e-10\RMSF =1.863e-04\Thermal=0.\Dipole=0.,0.,0.\PG=TD [O(C1),4C3(H1)]\\@ chch-base 1\1\GINC-X142\FOpt\RHF\6-31+G(d)\C2H1(1-)\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\-1,1\c,0.,0.,0.0248461948\c,0.,0.,1.2574248767\h,0.,0.,-1.0362710715\\version=em64 L-G03RevE.01\State=1-SG\HF=-76.2101485\RMSD=6.245e-09\RMSF=9.552e-06\T hermal=0.\dipole=0.,0.,-1.3582756\pg=c*v [C*(H1C1C1)]\\@ chch 1\1\GINC-X143\FOpt\RHF\6-31+G(d)\C2H2\JMH502\09-Jul-2010\0\\# HF/6-31+ G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.,0.,0.07 34588118\C,0.,0.,1.2615411882\H,0.,0.,2.3191313168\H,0.,0.,-0.98413131 68\\Version=EM64L-G03RevE.01\State=1-SGG\HF=-76.8230702\RMSD=4.359e-09 \RMSF=3.884e-05\Thermal=0.\Dipole=0.,0.,0.\PG=D*H [C*(H1C1.C1H1)]\\@ h+ch3coch3 1\1\GINC-X89\FOpt\RHF\6-31+G(d)\C3H7O1(1+)\JMH502\09-Jul-2010\0\\# HF/ 6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\c,0.020 4790443,0.0463141356,-0.0232598185\O,-0.0239211037,0.2304503677,1.2192 989875\C,1.3088446157,-0.0509373538,-0.7515870534\C,-1.2851119662,-0.0 656419684,-0.7107203313\H,1.2387021937,0.4701452161,-1.6988543742\H,2. 1453972946,0.3239946146,-0.176811154\H,1.4721794675,-1.1044334597,-0.9 755459008\H,-1.2230098663,-0.757369428,-1.5407341531\H,-2.0670775225,- 0.3436750347,-0.0192422708\H,-1.5105594623,0.919702709,-1.1188850658\H,0.8197458947,0.3314502016,1.6640078011\\Version=EM64L-G03RevE.01\Stat e=1-a\hf=-192.2897672\rmsd=5.763e-09\rmsf=9.141e-06\thermal=0.\dipole= 0.6588095,0.0158789,-0.1072197\PG=C01 [X(C3H7O1)]\\@ h+ch3nh2 1\1\GINC-X128\FOpt\RHF\6-31+G(d)\C1H6N1(1+)\JMH502\09-Jul-2010\0\\# HF /6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\n,0.00 1043961,0.0018081935,0.0002024632\H,0.0202940579,0.0351503396,1.010803 7816\H,0.9601990632,0.0349171679,-0.3187113582\H,-0.449860377,0.849015 3653,-0.3187113584\C,-0.7094021468,-1.2287205613,-0.5018343312\H,-1.72 13689695,-1.207073365,-0.1307227858\H,-0.6970491448,-1.2073245345,-1.5 796369612\H,-0.1846717138,-2.0942859394,-0.1307227855\\Version=EM64L-G 03RevE.01\State=1-A'\HF=-95.5741592\RMSD=7.753e-09\RMSF=3.365e-05\Ther mal=0.\dipole=0.4136478,0.716459,0.2923118\pg=cs [SG(C1H2N1),X(H4)]\\@ h+ch3och3 1\1\GINC-X143\FOpt\RHF\6-31+G(d)\C2H7O1(1+)\JMH502\09-Jul-2010\0\\# HF /6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\c,0.07 07612038,0.0860185158,0.085487774\H,-0.0313648944,-0.0406204615,1.1491 394173\H,1.0997779163,0.1188324346,-0.232446028\O,-0.5681112252,-1.101 0571488,-0.524885302\H,-0.4973269652,0.9289790572,-0.2656579811\C,-0.6 661293891,-1.1903134306,-1.9987535667\H,-1.2160871403,-2.0926195842,-2.2017611181\H,-1.2173462479,-0.3181309228,-2.3021800505\H,0.3317874072,-1.2113661469,-2.4046512155\H,-0.3045648256,-1.9248005664,-0.11362526 22\\Version=EM64L-G03RevE.01\State=1-A'\HF=-154.3840524\RMSD=6.460e-09 \RMSF=4.728e-05\Thermal=0.\Dipole=0.2888246,-0.3457958,0.1096409\PG=CS [SG(H1O1),X(C2H6)]\\@ h+ch3oh 1\1\GINC-X126\FOpt\RHF\6-31+G(d)\C1H5O1(1+)\JMH502\09-Jul-2010\0\\# HF /6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\c,0.06 38965013,-0.0810902615,0.0159382641\H,-0.027218615,0.0125545737,1.0828 286663\H,1.0812438895,-0.0776775812,-0.3330993345\H,-0.5231060658,-0.8 937009725,-0.3717711282\O,-0.609619579,1.1587894094,-0.5273403275\H,-0.2825008141,1.9998440281,-0.1942277536\H,-0.7214004863,1.1970734192,-1.4816617199\\Version=EM64L-G03RevE.01\State=1-A\HF=-115.3406593\RMSD=3.316e-09\RMSF=1.328e-04\Thermal=0.\Dipole=0.2199795,0.5521861,-0.41883 88\PG=C01 [X(C1H5O1)]\\@ h+ch3sh 1\1\GINC-X127\FOpt\RHF\6-31+G(d)\C1H5S1(1+)\JMH502\09-Jul-2010\0\\# HF S9
/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\s,-0.0 900034504,-0.1705055809,-0.1088905772\H,-0.0015541387,0.0337004746,1.2 010085145\C,1.6656815216,-0.0108409876,-0.6076527002\H,-0.552001127,1. 0362227851,-0.4169555589\H,1.6790095475,0.0032544039,-1.6874773843\H,2.0899271653,0.8897892276,-0.1939924242\H,2.1711138492,-0.892455546,-0. 2420398696\\Version=EM64L-G03RevE.01\State=1-A\HF=-438.0018246\RMSD=1. 597e-09\RMSF=1.055e-04\Thermal=0.\Dipole=-0.0371747,0.4725544,0.305647 6\PG=C01 [X(C1H5S1)]\\@ h+h2o 1\1\GINC-X128\FOpt\RHF\6-31+G(d)\H3O1(1+)\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\o,0.0348 06371,0.0602864031,-0.0151295735\H,-0.0060010134,-0.0103940601,0.95019 15736\H,0.9406690915,0.0164194026,-0.355531\H,-0.456114926,0.822853031 1,-0.355531\\Version=EM64L-G03RevE.01\State=1-A'\HF=-76.290605\RMSD=1. 634e-09\RMSF=3.779e-05\Thermal=0.\Dipole=0.2923373,0.5063431,0.2223571 \PG=CS [SG(H1O1),X(H2)]\\@ h+h2s 1\1\GINC-X144\FOpt\RHF\6-31+G(d)\H3S1(1+)\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\s,-0.106 4256147,-0.1843345718,-0.1223802674\H,0.00171796,0.002975594,1.1910220 044\H,1.1720842213,0.0369793622,-0.4223208688\H,-0.5540170436,1.033544 3921,-0.4223208688\\Version=EM64L-G03RevE.01\State=1-A'\HF=-398.942746 8\RMSD=3.696e-09\RMSF=1.504e-04\Thermal=0.\Dipole=0.3166308,0.5484206, 0.240749\PG=CS [SG(H1S1),X(H2)]\\@ h+me3n 1\1\GINC-X128\FOpt\RHF\6-31+G(d)\C3H10N1(1+)\JMH502\09-Jul-2010\0\\# H F/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\n,-0. 0468134321,0.,0.0165510476\C,0.0150085997,0.,1.5100864988\H,0.90434400 26,0.,-0.3197338884\C,-0.6993544359,1.2373130727,-0.510437288\C,-0.699 3544359,-1.2373130727,-0.510437288\H,-1.7213802533,-1.260670335,-0.163 3999386\H,-0.6742203863,-1.2149389521,-1.5892261763\H,-0.1634045834,-2.0996978761,-0.1444209036\H,-0.993531896,0.,1.8952660978\H,0.538040747 7,-0.8847589239,1.8395660973\H,0.5380407477,0.8847589239,1.8395660973\ H,-1.7213802533,1.260670335,-0.1633999386\H,-0.1634045834,2.0996978761,-0.1444209036\H,-0.6742203863,1.2149389521,-1.5892261763\\Version=EM6 4L-G03RevE.01\State=1-A1\HF=-173.6516129\RMSD=3.256e-09\RMSF=1.219e-04 \Thermal=0.\Dipole=0.3382414,0.,-0.1195864\PG=C03V [C3(N1H1),3SGV(C1H1 ),X(H6)]\\@ h+nh3 1\1\GINC-X136\FOpt\RHF\6-31+G(d)\H4N1(1+)\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\n,-0.005 4239946,-0.0093946342,-0.0044214273\H,-0.0054729984,-0.0094795113,1.00 88959562\H,0.9499538004,-0.0094787834,-0.3422627393\H,-0.4831857675,0. 8179447319,-0.3422627393\H,-0.4832125022,-0.8369486046,-0.3422823836\\ Version=EM64L-G03RevE.01\State=1-A'\HF=-56.5312766\RMSD=7.822e-10\RMSF =7.329e-05\Thermal=0.\Dipole=-0.0001078,-0.0001868,-0.0001115\PG=CS [S G(H2N1),X(H2)]\\@ h+phnh2 1\1\GINC-X141\FOpt\RHF\6-31+G(d)\C6H8N1(1+)\JMH502\09-Jul-2010\0\\# HF /6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\1,1\c,0.04 2719752,0.,0.0218610454\C,0.0039940026,0.,1.4030628587\C,1.2077162269, 0.,2.0879821996\C,2.4086986496,0.,1.3890518503\C,2.4154501445,0.,0.003 3428567\C,1.2176975189,0.,-0.6990616253\H,-0.9288593162,0.,1.940093805 \H,1.2061505673,0.,3.1617460054\H,3.3381884066,0.,1.9270338427\H,3.344 3792266,0.,-0.5351767665\H,1.2208287841,0.,-1.7752458944\N,-1.24591431 28,0.,-0.7143450595\H,-1.0972253194,0.,-1.7145667264\H,-1.8037724445,- 0.8164227653,-0.497889196\H,-1.8037724445,0.8164227653,-0.497889196\\V ersion=em64l-g03reve.01\state=1-a'\hf=-286.0930091\rmsd=4.815e-09\rmsf =1.037e-04\Thermal=0.\Dipole=-2.5038357,0.,-1.430646\PG=CS [SG(C6H6N1),X(H2)]\\@ h2co 1\1\GINC-X141\FOpt\RHF\6-31+G(d)\C1H2O1\JMH502\09-Jul-2010\0\\# HF/6-3 S10
1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.,0.,0. 0241194283\O,0.,0.,1.210013384\H,0.9263976689,0.,-0.5515664062\H,-0.92 63976689,0.,-0.5515664062\\Version=EM64L-G03RevE.01\State=1-A1\HF=-113.8711568\RMSD=3.401e-09\RMSF=1.966e-05\Thermal=0.\Dipole=0.,0.,-1.1342 683\PG=C02V [C2(C1O1),SGV(H2)]\\@ h2o-base 1\1\GINC-X126\FOpt\RHF\6-31+G(d)\H1O1(1-)\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\-1,1\o,0.,0.,-0.0026963174\h,0.,0.,0.9496963174\\version=em64l-g03reve.01\state=1- SG\HF=-75.376424\RMSD=2.134e-09\RMSF=4.117e-05\Thermal=0.\Dipole=0.,0.,0.7758319\PG=C*V [C*(H1O1)]\\@ h2o 1\1\GINC-X128\FOpt\RHF\6-31+G(d)\H2O1\JMH502\09-Jul-2010\0\\# HF/6-31+ G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\o,-0.0098496 997,0.,-0.0082607566\H,0.0139545322,0.,0.9390582242\H,0.8915637569,0., -0.3004641342\\Version=EM64L-G03RevE.01\State=1-A'\HF=-76.0177432\RMSD =2.146e-09\RMSF=1.272e-05\Thermal=0.\Dipole=0.7337404,0.,0.5195279\PG= CS [SG(H2O1)]\\@ h2s-base 1\1\GINC-X134\FOpt\RHF\6-31+G(d)\H1S1(1-)\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\-1,1\s,0.,0.,-0.1962501864\h,0.,0.,1.1432501864\\version=em64l-g03reve.01\state=1- SG\HF=-398.1068939\RMSD=4.201e-09\RMSF=1.380e-08\Thermal=0.\Dipole=0., 0.,0.4138345\PG=C*V [C*(H1S1)]\\@ h2s 1\1\GINC-X136\FOpt\RHF\6-31+G(d)\H2S1\JMH502\09-Jul-2010\0\\# HF/6-31+ G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\s,-0.1704275 341,0.,-0.1483305896\H,-0.0095949084,0.,1.1678381893\H,1.1303739564,0.,-0.4085075996\\Version=EM64L-G03RevE.01\State=1-A'\HF=-398.6681144\RM SD=6.093e-09\RMSF=1.673e-04\Thermal=0.\Dipole=0.4595181,0.,0.3322677\P G=CS [SG(H2S1)]\\@ hcn-base 1\1\GINC-X126\FOpt\RHF\6-31+G(d)\C1N1(1-)\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\-1,1\n,0.,0.,-0.0363139594\c,0.,0.,1.1253139594\\version=em64l-g03reve.01\state=1- SG\HF=-92.3148718\RMSD=3.657e-09\RMSF=1.055e-04\Thermal=0.\Dipole=0.,0.,-0.1609274\PG=C*V [C*(C1N1)]\\@ hcn 1\1\GINC-X126\FOpt\RHF\6-31+G(d)\C1H1N1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\h,0.,0.,0. 1216429445\C,0.,0.,1.1816614599\N,0.,0.,2.3146955956\\Version=EM64L-G0 3RevE.01\State=1-SG\HF=-92.8786346\RMSD=4.519e-09\RMSF=3.576e-05\Therm al=0.\dipole=0.,0.,-1.3009175\pg=c*v [C*(H1C1N1)]\\@ hcooh-base 1\1\GINC-X127\FOpt\RHF\6-31+G(d)\C1H1O2(1-)\JMH502\09-Jul-2010\0\\# HF /6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\-1,1\c,0.0 388423446,0.,-0.0734035277\H,0.0440507796,0.,1.0439098774\O,1.15766133 54,0.,-0.5955261591\O,-1.0846698869,0.,-0.5849801906\\Version=EM64L-G0 3RevE.01\State=1-A'\HF=-188.2081944\RMSD=7.914e-09\RMSF=8.365e-05\Ther mal=0.\dipole=0.003092,0.,0.7635097\pg=cs [SG(C1H1O2)]\\@ hcooh 1\1\GINC-X128\FOpt\RHF\6-31+G(d)\C1H2O2\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,-0.02529 86416,0.,-0.0453919992\H,0.0858609456,0.,1.0316347618\O,1.1578541434,0.,-0.6355980812\O,-1.0638785847,0.,-0.6127450148\H,1.0401893583,0.,-1. 5819047518\\Version=EM64L-G03RevE.01\State=1-A'\HF=-188.7691846\RMSD=8.828e-09\RMSF=3.583e-05\Thermal=0.\Dipole=0.6634328,0.,0.087327\PG=CS [SG(C1H2O2)]\\@ me3n S11
1\1\GINC-X101\FOpt\RHF\6-31+G(d)\C3H9N1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,-0.02476 68937,-0.0009090303,0.0093130843\H,-0.0074952494,-0.0265155088,1.09291 70833\N,1.3260605192,0.05470596,-0.5023336146\H,-0.513797727,-0.903457 124,-0.3391225777\H,-0.6311762512,0.8568586294,-0.3015621023\C,1.35816 98488,-0.0009090303,-1.9464548128\C,2.04963822,1.1967493205,0.00931308 43\H,2.3855587113,-0.0265155088,-2.2913722833\H,0.8666512784,-0.903457 124,-2.2913722833\H,0.8629374595,0.8568586294,-2.4145579757\H,3.075783 214,1.1689883985,-0.3391225777\H,1.6099943149,2.1507990591,-0.30156210 23\H,2.0631782587,1.1689883985,1.0929170833\\Version=EM64L-G03RevE.01\ State=1-A1\HF=-173.2729064\RMSD=8.191e-09\RMSF=2.717e-05\Thermal=0.\Di pole=-0.1403966,0.243174,-0.0992754\pg=c03v [C3(N1),3SGV(C1H1),X(H6)]\ \@ nh3 1\1\GINC-X126\FOpt\RHF\6-31+G(d)\H3N1\JMH502\09-Jul-2010\0\\# HF/6-31+ G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\n,-0.0137776 094,-0.0238635196,-0.0108420022\H,-0.0023331647,-0.0040411598,0.990568 4366\H,0.9346005996,-0.0034746107,-0.3349831465\H,-0.470309401,0.80765 05563,-0.3349831465\\Version=EM64L-G03RevE.01\State=1-A'\HF=-56.189498 6\RMSD=5.154e-09\RMSF=3.469e-04\Thermal=0.\Dipole=0.3451105,0.5977489, 0.2432197\PG=CS [SG(H1N1),X(H2)]\\@ phcho 1\1\GINC-X128\FOpt\RHF\6-31+G(d)\C7H6O1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.026756 8427,0.,-0.0101945918\C,0.0156988073,0.,1.379336421\C,1.2085838425,0., 2.0887089163\C,2.4129575827,0.,1.4022400699\C,2.4297206173,0.,0.010614 0157\C,1.2403758738,0.,-0.6951585954\H,-0.9225069124,0.,1.9078913399\H,1.19823914,0.,3.1637911264\H,3.3397551304,0.,1.9481490115\H,3.3676127 943,0.,-0.5151816918\H,1.2348551903,0.,-1.7693778221\C,-1.2584651708,0.,-0.751653977\O,-1.3556880359,0.,-1.9393959852\H,-2.1558794251,0.,-0. 1257682375\\Version=EM64L-G03RevE.01\State=1-A'\HF=-343.4439073\RMSD=4.756e-09\RMSF=1.161e-04\Thermal=0.\Dipole=0.5956645,0.,1.2998916\PG=CS [SG(C7H6O1)]\\@ phcl 1\1\GINC-X136\FOpt\RHF\6-31+G(d)\C6H5Cl1\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.04888 93716,0.,0.0282262918\C,0.0337965619,0.,1.4123054075\C,1.2385165793,0.,2.1003253472\C,2.4413572319,0.,1.409518255\C,2.4381933965,0.,0.022424 1471\C,1.2399906418,0.,-0.6768840226\H,-0.901107571,0.,1.9404613576\H, 1.2330078804,0.,3.1755146304\H,3.3723853172,0.,1.9470475707\H,3.366580 2802,0.,-0.5199411677\H,1.2299350453,0.,-1.7506127269\Cl,-1.4616518509,0.,-0.8438850896\\Version=EM64L-G03RevE.01\State=1-A1\HF=-689.6101603 \RMSD=8.017e-10\RMSF=2.121e-05\Thermal=0.\Dipole=0.7046206,0.,0.406812 9\PG=C02V [C2(H1C1C1Cl1),SGV(C4H4)]\\@ phnh2 1\1\GINC-X89\FOpt\RHF\6-31+G(d)\C6H7N1\JMH502\09-Jul-2010\0\\# HF/6-31 +G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,-0.004545 0787,0.0001226318,-0.0027045042\C,-0.0065758746,-0.0005273295,1.390893 0938\C,1.1873027311,0.0027057021,2.0937091913\C,2.4047540106,0.0046108 652,1.428149779\C,2.4065899123,0.0027048906,0.0406512893\C,1.218167393 1,-0.0005281335,-0.671353318\H,-0.9429543378,-0.0110779331,1.922516128 7\H,1.1628618443,0.0025779154,3.1693693297\H,3.3289276646,0.0070963743,1.9770054085\H,3.3394058041,0.0025766003,-0.495535767\H,1.2368962591, -0.0110796071,-1.747957591\N,-1.2060518531,-0.0556783082,-0.7162648922 \H,-1.153965711,0.3185538966,-1.6397785793\H,-1.9920434617,0.318550531,-0.2286069947\\Version=EM64L-G03RevE.01\State=1-A\HF=-285.7410373\RMS D=8.624e-09\RMSF=1.522e-04\Thermal=0.\Dipole=-0.2999323,0.4648749,-0.1 781248\PG=C01 [X(C6H7N1)]\\@ phno2 1\1\GINC-X126\FOpt\RHF\6-31+G(d)\C6H5N1O2\JMH502\09-Jul-2010\0\\# HF/6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.0336 646867,0.,0.0194518036\C,0.005203738,0.,1.4033574914\C,1.2086328178,0.,2.0889692111\C,2.4082100785,0.,1.3903740572\C,2.4134032157,0.,0.00221 S12
21486\C,1.2179216989,0.,-0.6971652697\H,-0.93213578,0.,1.9223248439\H, 1.2080026321,0.,3.1634578471\H,3.3393089706,0.,1.9279353919\H,3.343615 0845,0.,-0.5355909745\H,1.1986758986,0.,-1.7684086901\N,-1.232224818,0.,-0.7113999153\O,-1.1835205169,0.,-1.9047910051\O,-2.2413737754,0.,-0.0725157962\\Version=EM64L-G03RevE.01\State=1-A'\HF=-434.1879813\RMSD= 6.281e-09\RMSF=3.313e-05\Thermal=0.\Dipole=1.7654129,0.,1.0192473\PG=C S [SG(C6H5N1O2)]\\@ phoh-base 1\1\GINC-X136\FOpt\RHF\6-31+G(d)\C6H5O1(1-)\JMH502\09-Jul-2010\0\\# HF /6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\-1,1\c,-0. 0637771109,0.,-0.0368217321\C,0.0104753301,0.,1.4000532346\C,1.2122575 703,0.,2.0761410399\C,2.4394541318,0.,1.4084194997\C,2.4041196676,0.,0.0117753318\C,1.2177193329,0.,-0.6909547153\H,-0.9212979574,0.,1.94244 80714\H,1.2006573975,0.,3.1569000275\H,3.3723347835,0.,1.947018395\H,3.3342843198,0.,-0.5386502063\H,1.2215603966,0.,-1.7690914713\O,-1.1478 949787,0.,-0.6627374749\\Version=EM64L-G03RevE.01\State=1-A1\HF=-304.9 953591\RMSD=7.967e-09\RMSF=3.558e-05\Thermal=0.\Dipole=1.7344113,0.,1. 0013628\PG=C02V [C2(H1C1C1O1),SGV(C4H4)]\\@ phoh 1\1\GINC-X137\FOpt\RHF\6-31+G(d)\C6H6O1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.019222 0122,0.,-0.0082015445\C,0.0087814992,0.,1.3807704309\C,1.2071095255,0.,2.0726675868\C,2.4210994099,0.,1.3953151176\C,2.4191982264,0.,0.01039 54798\C,1.2235407473,0.,-0.6960915806\H,-0.9343204847,0.,1.8957059019\ H,1.1930241658,0.,3.1482591361\H,3.3484218667,0.,1.938822958\H,3.34903 22744,0.,-0.5304133445\H,1.2318705729,0.,-1.7735047208\O,-1.1777240709,0.,-0.6397387099\H,-1.0687536984,0.,-1.5805423062\\Version=EM64L-G03R eve.01\state=1-a'\hf=-305.5683552\rmsd=9.572e-09\rmsf=9.516e-05\therma l=0.\dipole=0.3733518,0.,-0.4468137\pg=cs [SG(C6H6O1)]\\@ phsh-base 1\1\GINC-X138\FOpt\RHF\6-31+G(d)\C6H5S1(1-)\JMH502\09-Jul-2010\0\\# HF /6-31+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\-1,1\c,-0. 0031563355,0.,-0.0018223111\C,0.0480258132,0.,1.4047951655\C,1.2484741 795,0.,2.0972753494\C,2.4646751326,0.,1.4229808513\C,2.440530821,0.,0. 0325726807\C,1.240601207,0.,-0.6608060084\H,-0.88056778,0.,1.947376033 7\H,1.2346346811,0.,3.1761216625\H,3.3977551652,0.,1.9616948593\H,3.36 79193858,0.,-0.518835833\H,1.2461932259,0.,-1.736282084\S,-1.525192613 1,0.,-0.8805703657\\Version=EM64L-G03RevE.01\State=1-A1\HF=-627.668217 6\RMSD=5.227e-09\RMSF=1.080e-04\Thermal=0.\Dipole=2.5801331,0.,1.48964 05\PG=C02V [C2(H1C1C1S1),SGV(C4H4)]\\@ phsh 1\1\GINC-X101\FOpt\RHF\6-31+G(d)\C6H6S1\JMH502\09-Jul-2010\0\\# HF/6-3 1+G(d) opt freq=noraman maxdisk=458752000\\hf geom opt\\0,1\c,0.113670 2082,0.1400887759,-0.0545067558\C,0.0561882521,0.0308329542,1.33008962 78\C,1.2253566088,-0.070287011,2.0704752771\C,2.4568281415,-0.05513390 17,1.4322347209\C,2.5175294666,0.0645209274,0.0515762168\C,1.349492868 1,0.1658186967,-0.6904780888\H,-0.8978711919,0.0264783617,1.8240717056 \H,1.1725051323,-0.1571118285,3.1410802163\H,3.3626515687,-0.131288687,2.0069085808\H,3.4696883133,0.0825700129,-0.4480143338\H,1.3956556325,0.2660256661,-1.7591735322\S,-1.3943965049,0.3112786921,-1.0081634587 \H,-1.613718874,-0.9791619792,-1.2360247633\\Version=EM64L-G03RevE.01\ State=1-A\HF=-628.21784\RMSD=9.489e-09\RMSF=1.084e-05\Thermal=0.\Dipol e=0.5121317,-0.429942,0.2987244\pg=c01 [X(C6H6S1)]\\@ S13
Table S5. Some Typical Output Summaries for CSM Calculations Example 1. Output from a PCM calculation in Gaussian03. -------------------------------------------------------------------- Variational C-PCM results ========================= <psi(0) H psi(0)> (a.u.) = -76.016806 <psi(0) H+V(0)/2 psi(0)> (a.u.) = -76.028894 <psi(0) H+V(f)/2 psi(0)> (a.u.) = -76.030130 <psi(f) H psi(f)> (a.u.) = -76.015436 <psi(f) H+V(f)/2 psi(f)> (a.u.) = -76.030136 Total free energy in solution: with all non electrostatic terms (a.u.) = -76.028988 -------------------------------------------------------------------- (Unpolarized solute)-solvent (kcal/mol) = -7.59 (Polarized solute)-solvent (kcal/mol) = -9.22 Solute polarization (kcal/mol) = 0.86 Total electrostatic (kcal/mol) = -8.36 -------------------------------------------------------------------- Cavitation energy (kcal/mol) = 4.45 Dispersion energy (kcal/mol) = -5.18 Repulsion energy (kcal/mol) = 1.45 Total non electrostatic (kcal/mol) = 0.72 DeltaG (solv) (kcal/mol) = -7.64 -------------------------------------------------------------------- This term is actually E soln + G nes not the actual G soln as indicated Example 2. Output from an SM6 solvation calculation in GAMESSPLUS. Summary of SM6 solvation calculation by GAMESSPLUS version 2008 at 298 K -------------------------------------------------------------------------------- Options: ISCRF = 2, IGAS = 0, ICMD =418, ICDS =418, IAQU = 1, DIELEC = 78.40 (0) E-EN(g) gas-phase B3LYP3 elect-nuc energy -76.422487257 a.u. (1) E-EN(liq) elect-nuc B3LYP3 energy of solute -76.421937128 a.u. (2) G-P(liq) polarization free energy of solvation -6.391 kcal/mol (3) G-ENP(liq) elect-nuc-pol free energy of system -76.432122415 a.u. (4) G-CDS(liq) cavity-dispersion-solvent structure -3.320 kcal/mol (5) G-P-CDS(liq) = G-P(liq) + G-CDS(liq) = (2) + (4) -9.711 kcal/mol (6) G-S(liq) free energy of system = (1) + (5) -76.437413156 a.u. (7) DeltaE-EN(liq) elect-nuc reorganization energy of solute molecule (7) = (1) - (0) 0.345 kcal/mol (8) DeltaG-ENP(liq) elect-nuc-pol free energy of solvation (8) = (3) - (0) -6.046 kcal/mol (9) DeltaG-S(liq) free energy of solvation (9) = (6) - (0) -9.366 kcal/mol This term is actually E soln + G nes not the actual G soln as indicated S14
Example 3. Output from a PCM calculation in GAMESS. ------- RESULTS OF PCM CALCULATION ------- FREE ENERGY IN SOLVENT = <PSI H(0)+V/2 PSI> = -646.9902225852 A.U. INTERNAL ENERGY IN SOLVENT = <PSI H(0) PSI> = -646.9442611987 A.U. DELTA INTERNAL ENERGY = <D-PSI H(0) D-PSI> = 0.0000000000 A.U. ELECTROSTATIC INTERACTION = -0.0459613865 A.U. PIEROTTI CAVITATION ENERGY = 0.0000000000 A.U. DISPERSION FREE ENERGY = 0.0000000000 A.U. REPULSION FREE ENERGY = 0.0000000000 A.U. TOTAL INTERACTION (DELTA + ES + CAV + DISP + REP) = -0.0459613865 A.U. TOTAL FREE ENERGY IN SOLVENT = -646.9902225852 A.U. FREE ENERGY IN SOLVENT = -405992.54 KCAL/MOL INTERNAL ENERGY IN SOLVENT = -405963.70 KCAL/MOL DELTA INTERNAL ENERGY = 0.00 KCAL/MOL ELECTROSTATIC INTERACTION = -28.84 KCAL/MOL PIEROTTI CAVITATION ENERGY = 0.00 KCAL/MOL DISPERSION FREE ENERGY = 0.00 KCAL/MOL REPULSION FREE ENERGY = 0.00 KCAL/MOL TOTAL INTERACTION = -28.84 KCAL/MOL TOTAL FREE ENERGY IN SOLVENT = -405992.54 KCAL/MOL This term is actually E soln + G nes not the actual G soln as indicated -INTERNAL ENERGY IN SOLVENT- OMITS ES,CAV,DISP,REP (USES SOLVATED ORBITALS IN THE GAS PHASE HAMILTONIAN) -FREE ENERGY IN SOLVENT- INCLUDES ES+DISP+REP WHICH ARE IN THE SELF-CONSISTENT WAVEFUNCTION. -TOTAL FREE ENERGY IN SOLVENT- INCLUDES ES+DISP+REP+CAV, MEANING CAVITATION IS NOT IN THE SCF ENERGY. S15