Using Web-Based Computations in Organic Chemistry

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10/30/2017 1 Using Web-Based Computations in Organic Chemistry John Keller UAF Department of Chemistry & Biochemistry The UAF WebMO site Practical aspects of computational chemistry theory and nomenclature MOPAC2016: fast and approximate NWChem: slow and accurate Example tasks: Energy, Optimization, vibrational spectra; UV spectra.

10/30/2017 2 Click here to log in (guest/webmo or yourusername/password) https://chem2.uaf.edu/facilities/webmo/

10/30/2017 3 How does a WebMO job work? webserver world wide web User Draw molecule & choose options WebMO creates input file for MOPAC or NWChem When the job is done, the output file is parsed and shown on Results page. The updated, intermediate results can be visualized in the Job Manager. compute servers obsidian antec12 (& others). Running Gaussian, MOPAC, and NWChem

10/30/2017 4 User Accounts MOPAC NWChem Gaussian CPU job time limit (h) guest 4 uaaguest 12 Non-UAF unlimited UAF unlimited Machines Server Cores Procs Mem (GB) CPU Gaussian 09 NWChem 6.6 Chemlinux1 8 8 16 Xeon (2) Chemlinux2 8 8 32 Xeon (2) Chemlinux3 8 8 32 Xeon (2) Antec12 6 12 32 Core i7 5820K Corsair3 10 20 64 Core i7 6950X Obsidian 6 12 32 Core i7 930 MOPAC 2016

10/30/2017 5 Levels of theory Correlated ab initio MO (MP2 & others) Molecular mechanics (MM+, OPLS, etc) Ball-andspring model no orbitals no electronics Semi-empirical MO (PM3, PM6, PM7) Uses 27 orbital parameters for each element Parameters derived from stable molecules Electron correlation implicit, since the parameters are fr real molecules, where actual electron correlation occurs. Ab initio MO (Hartree-Fock HF) MOs = linear combination of basis orbitals. Parameters derived from isolated atoms Some electron correlation Density Functional Theory (DFT) (B3LYP ) MOs = linear combination of basis orbitals. 3-25 Parameters derived from atoms and molecular databases More electron correlation MOs = linear combination of basis orbitals. Parameters derived from isolated atoms Includes excited state configurations Most electron correlation

10/30/2017 6 Basic WebMO and MOPAC 1) Build hexatriene; load and modify morphine. 2) Optimize Use MOPAC PM7

10/30/2017 7 Log in

10/30/2017 8 Begin with New Job, Create New Job

10/30/2017 9

10/30/2017 10 Select with mouse. Then use the Adjust menu to change torsion angles, bond distances

10/30/2017 11 Optimize your molecule 1) Right Arrow 2) Engine: MOPAC 3) Select Server: First Available

10/30/2017 12 Enter an informative Job Name Type of calculation Geometry Optimization Theory: PM7 (a recent version of PM3 semi-empirical) Charge: (0 for molecule) Multiplicity: generally singlet (unless odd # of valence e - )

10/30/2017 13 Generate on the Preview tab shows the input file automatically created by WebMO. It can be modified manually. Submit job by clicking the right arrow

10/30/2017 14

10/30/2017 15 NWChem software Review MOs Basis sets Performance comparison: system size and basis set choice Typical NWChem jobs: Energy, Opt, Vibrations, UV

10/30/2017 16 On-line NWChem User s Reference http://www.nwchemsw.org/index.php/release66:nwchem_documentation

H 2 MOs: formed by linear combination of 1s atomic orbitals. 17 Electron density (0.008 e/å 3 ) node node anti-bonding MO H atom H atom bonding MO 1s AO 1s AO d = 0.76 Å d = 2.8 Å d =

18 In semi-empirical MO theory (PM6 and others), molecular orbitals are formed by linear combinations of s, (and on heavy atoms) p x, p y, and p z AOs. s p x p y p z The orbital functions on the constituent atoms are the basis set.

10/30/2017 19 NWChem and other QM programs use larger basis sets. The most common are split-valence basis sets. Basis orbital for core electrons of 2 nd row atom contains 6 Gaussian terms. 6-31G(d) 2 nd row atoms have an additional set of six d-type orbitals. Inner valence shell orbital contains 3 Gaussian terms. Outer valence shell orbital contains 1 Gaussian. H 2 O has 19 orbitals in the 6-31G(d) basis. O: 1s + 2s,2p x,2p y,2p z + (2s,2p x,2p y,2p z ) + 2(d xx,d yy,d zz,d xy,d yz,d xz ) H: - 1s + (1s) H: - 1s + (1s)

10/30/2017 20 Tetracycline (32) Vitamin B-6 (16) a-cyclodextrin (66) SO 2 -formic acid (6 heavy atoms)

10/30/2017 21 # Heavy atoms Basis set/# of basis orbitals 3-21G 6-31G(d,p) 6-311++G(2d,2p) 6-311++G(3df,3pd) SO 2 -formic acid 6 95 155 301 449 Vitamin B-6 16 164 268 520 776 Tetracycline 32 336 568 1104 a-cyclodextrin 66 714 1224

10/30/2017 22 ~ 20 optimization steps 6.5 da 20 h Basis set Basis set small large Small molecule OK OK Large molecule OK (no) Hartree-Fock; Corsair3; 10 processors

10/30/2017 23 NWChem input file format Energy Geometry Optimization Vibrational Frequency UV spectrum

10/30/2017 24 NWChem input file format Energy (single point) Job name charge molecular description Basis set theory multiplicity Calculation type

10/30/2017 25 NWChem input file format WebMO default - Optimization

10/30/2017 26 You may wish to add sections to modify some parts of the input file. scf noprint "final vectors analysis" singlet end driver maxiter 100 end NWChem stops after 20 optimization steps by default so, increase the limit this way. task scf optimize

10/30/2017 27 Geometry Optimization View Results

10/30/2017 28 NWChem input file format - Vibrational frequencies title "H2O-631Gs-HF-Freq" echo charge 0 geometry O 0.00000000 0.00000000 0.00000000 H 1.05000000 0.00000000 0.00000000 H -0.35000000 0.00000000 0.98994949 end basis noprint * library 6-31G* end scf noprint "final vectors analysis" singlet end task scf freq Sally 3249 pulegone vib

10/30/2017 29 Vibrational Frequencies View Results

10/30/2017 30 From Japan Spectral database Pulegone Exp tl B3LYP/6-31G(d) HF/6-31G(d) (This is why one should use HF or DFT methods for IR.)? PM7

10/30/2017 31 UV-Vis spectra More conjugated double bonds lead to lower energy gap, lower frequency and longer wavelength. DE = hn = hc/l

10/30/2017 32 NWChem CIS (configuration interaction singles) mixes 10 single excited states Etc

10/30/2017 33 UV-Vis spectra

10/30/2017 34

10/30/2017 35 2 C=C 3 5 9 11 7 yellow 7 5 3 2 Plot line colors are arbitrary. 9 yellow-orange 11 orange-red

10/30/2017 36 Your questions