Abstract
New developments in computational chemistry which allow an accurate
treatment of large molecules are presented. Along with a short introduction
to the theoretical methods, highlights of current applications in
organic chemistry are given. The so-called ‘chemical accuracy’ is
now often achievable when modern methods and sophisticated techniques
are applied.
1 Introduction
2 Short Review of Theoretical Methods
3 Exemplary Applications
3.1 An Instructive Example: Alkane-Branching
3.2 Relative Stability of 5-Benzylimidazolidin-4-one Derivative
Conformers
3.3 Dibenzocyclic[3.2.2]nonanes: Solvent
Effects on Intramolecular van der Waals Interactions
3.4 Isomerizations of Large Molecules
3.5 Relative Energies of Epimeric Carbamate Complexes for Enantiomeric
Excess Prediction
3.6 Fullerenes as Dihydrogen Storage Containers: Accurate Encapsulation
Energies
4 Recommended Treatments
5 Conclusion
Key words
computational chemistry - theoretical methods - conformers - enantioselectivity -
fullerenes
References
<A NAME="RA55610ST-1">1 </A>
Jensen F.
Introduction
to Computational Chemistry
Wiley;
Chichester:
1999.
<A NAME="RA55610ST-2">2 </A>
Parr RG.
Yang W.
Densitiy
Functional Theory of Atoms and Molecules
Oxford
University Press;
New York:
1998.
<A NAME="RA55610ST-3">3 </A>
Koch W.
Holthausen C.
A
Chemist’s Guide to Density Functional Theory
Wiley-VCH;
Weinheim:
2000.
<A NAME="RA55610ST-4">4 </A>
von Arnim M.
Ahlrichs R.
J. Comput. Chem.
1998,
19:
1746
<A NAME="RA55610ST-5">5 </A>
Hättig C.
Hellweg A.
Köhn A.
Phys.
Chem. Chem. Phys.
2006,
8:
1159
<A NAME="RA55610ST-6">6 </A>
Woods CJ.
Brown P.
Manby FR.
J.
Chem. Theory Comput.
2009,
5:
1776
<A NAME="RA55610ST-7">7 </A>
Yasuda K.
J.
Comput. Chem.
2008,
29:
334
<A NAME="RA55610ST-8">8 </A>
Ufimtsev IS.
Martínez TJ.
J. Chem.
Theory Comput.
2008,
4:
222
<A NAME="RA55610ST-9">9 </A>
Weigend F.
Häser M.
Theor. Chem. Acc.
1997,
97:
331
10a </A>
Hättig C.
Weigend F.
J.
Chem. Phys.
2000,
113:
5154
10b </A>
Hättig C.
Kasper H.
Phys. Chem.
Chem. Phys.
2002,
4:
2111
<A NAME="RA55610ST-11">11 </A>
Weigend F.
Phys.
Chem. Chem. Phys.
2002,
4:
4285
<A NAME="RA55610ST-12">12 </A>
Ahlrichs R.
Phys.
Chem. Chem. Phys.
2004,
6:
5119
<A NAME="RA55610ST-13">13 </A>
Werner H.-J.
J.
Chem. Phys.
2008,
129:
101103
<A NAME="RA55610ST-14">14 </A>
Neese F.
Wennmohs F.
Hansen A.
J.
Chem. Phys.
2009,
130:
114108
15a </A>
Svensson M.
Humbel S.
Froese RDJ.
Matsubara T.
Sieber S.
Morokuma K.
J. Chem. Phys.
1996,
100:
19357
15b </A>
Senn HM.
Thiel W.
Curr. Opin.
Chem. Biol.
2007,
11:
182
15c </A>
Senn HM.
Thiel W.
Top. Curr.
Chem.
2007,
268:
173
<A NAME="RA55610ST-16">16 </A>
Grimme S.
J.
Chem. Phys.
2003,
118:
9095
17a </A>
Grimme S.
J. Chem. Phys.
2006,
124:
34108
17b </A>
Schwabe T.
Grimme S.
Phys. Chem. Chem. Phys.
2006,
8:
4398
17c </A>
Schwabe T.
Grimme S.
Phys. Chem. Chem. Phys.
2007,
9:
3397
<A NAME="RA55610ST-18">18 </A>
Grimme S.
Antony J.
Schwabe T.
Mück-Lichtenfeld C.
Org. Biomol.
Chem.
2007,
5:
741
<A NAME="RA55610ST-19">19 </A>
Grimme S.
Angew.
Chem. Int. Ed.
2006,
45:
4460 ; Angew. Chem. 2006 , 118 , 4571
<A NAME="RA55610ST-20">20 </A>
Schreiner PR.
Angew.
Chem. Int. Ed.
2007,
46:
4217
<A NAME="RA55610ST-21">21 </A>
Grimme S.
Angew.
Chem. Int. Ed.
2008,
47:
3430
22a </A>
Grimme S.
J. Comput. Chem.
2004,
25:
1463
22b </A>
Grimme S.
J.
Comput. Chem.
2006,
27:
1787
<A NAME="RA55610ST-23">23 </A>
Zhao Y.
Truhlar DG.
Acc. Chem. Res.
2008,
41:
157
<A NAME="RA55610ST-24">24 </A>
Schwabe T.
Grimme S.
Acc. Chem. Res.
2008,
41:
569
<A NAME="RA55610ST-25">25 </A>
Grimme S.
Gerenkamp M.
Chem. Phys. Lett.
2004,
392:
229
<A NAME="RA55610ST-26">26 </A>
Grimme S.
Antony J.
Ehrlich S.
Krieg H.
J. Chem. Phys.
2010,
132:
154104
<A NAME="RA55610ST-27">27 </A>
Karton A.
Tarnopolsky A.
Lamère J.-F.
Schatz GC.
Martin JML.
J. Phys. Chem. A
2008,
112:
12868
<A NAME="RA55610ST-28">28 </A>
Benighaus T.
DiStasio RA.
Lochan RC.
Chai
J.-D.
Head-Gordon M.
J. Phys. Chem. A
2008,
112:
2702
<A NAME="RA55610ST-29">29 </A>
Korth M.
Grimme S.
J. Chem. Theory Comput.
2009,
5:
993
30a </A>
Mori-Sánchez P.
Cohen AJ.
Yang W.
J. Chem. Phys.
2006,
125:
201102
30b </A>
Schwabe T.
Grimme S.
Eur. J. Org. Chem.
2008,
5928
31a </A>
Neese F.
Schwabe T.
Kossmann S.
Schirmer B.
Grimme S.
J. Chem. Theory Comput.
2009,
5:
3060
31b </A>
Schwabe T.
Dissertation
University
of Münster;
Germany:
2010.
<A NAME="RA55610ST-32">32 </A>
Piacenaz M.
Hyla-Kryspin I.
Grimme S.
J.
Comput. Chem.
2007,
28:
2275
<A NAME="RA55610ST-33">33 </A>
Grimme S.
Steinmetz M.
Korth M.
J.
Org. Chem.
2007,
72:
2118
34a </A>
Dunning TH.
J. Chem. Phys.
1989,
90:
1007
34b </A>
Weigend F.
Ahlrichs R.
Phys. Chem. Chem. Phys.
2005,
7:
3297
35a </A>
Grošelj U.
Schweizer WB.
Ebert M.-O.
Seebach D.
Helv. Chim. Acta
2008,
91:
1999
35b </A>
Brazier JB.
Evans G.
Gibbs TJK.
Coles SJ.
Hursthouse MB.
Platts
JA.
Tomkinson NCO.
Org.
Lett.
2009,
11:
133
<A NAME="RA55610ST-36">36 </A>
Seebach D.
Grošelj U.
Schweizer WB.
Grimme S.
Mück-Lichtenfeld C.
Helv. Chim. Acta
2010,
93:
1
<A NAME="RA55610ST-37">37 </A>
Gordillo R.
Carter J.
Houk KN.
Adv.
Synth. Catal.
2004,
346:
1175
<A NAME="RA55610ST-38">38 </A>
TURBOMOLE, V5.9, University of Karlsruhe, 2006 ; see: http://www.turbomole.com
39a </A>
Becke AD.
J. Chem. Phys.
1993,
98:
5648
39b </A>
Stephens PJ.
Devlin FJ.
Chabalowski CF.
Frisch MJ.
J.
Chem. Phys.
1994,
98:
11623
<A NAME="RA55610ST-40">40 </A>
Schäfer A.
Huber C.
Ahlrichs R.
J.
Chem. Phys.
1994,
100:
5829
<A NAME="RA55610ST-41">41 </A>
Motherwell WB.
Moïse J.
Aliev AE.
Nič M.
Coles SJ.
Horton PN.
Hursthouse MB.
Chessari G.
Hunter CA.
Vinter JG.
Angew.
Chem. Int. Ed.
2007,
46:
7823
<A NAME="RA55610ST-42">42 </A>
Klamt A.
Schürmann G.
J. Chem. Soc., Perkin
Trans. 2
1993,
799
<A NAME="RA55610ST-43">43 </A>
Perdew JP.
Phys.
Rev. B
1986,
33:
8822
<A NAME="RA55610ST-44">44 </A>
Krishnan R.
Binkley JS.
Seeger R.
Pople JA.
J. Chem. Phys.
1980,
72:
650
<A NAME="RA55610ST-45">45 </A>
Barone V.
Cossi M.
J. Phys. Chem. A
1998,
102:
1995
<A NAME="RA55610ST-46">46 </A>
Frisch MJ.
Trucks GW.
Schlegel HB.
Scuseria GE.
Robb MA.
Cheeseman JR.
Montgomery JA.
Vreven T.
Kudin KN.
Burant JC.
Millam JM.
Iyengar SS.
Tomasi J.
Barone V.
Mennucci B.
Cossi M.
Scalmani G.
Rega N.
Petersson GA.
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 JE.
Hratchian HP.
Cross JB.
Bakken V.
Adamo C.
Jaramillo J.
Gomperts R.
Stratmann RE.
Yazyev O.
Austin AJ.
Cammi R.
Pomelli C.
Ochterski JW.
Ayala PY.
Morokuma K.
Voth GA.
Salvador P.
Dannenberg JJ.
Zakrzewski VG.
Dapprich S.
Daniels AD.
Strain MC.
Farkas O.
Malick DK.
Rabuck AD.
Raghavachari K.
Foresman JB.
Ortiz JV.
Cui Q.
Baboul AG.
Clifford S.
Cioslowski J.
Stefanov BB.
Liu G.
Liashenko A.
Piskorz P.
Komaromi I.
Martin RL.
Fox DJ.
Keith T.
Al-Laham MA.
Peng CY.
Nanayakkara A.
Challacombe M.
Gill PMW.
Johnson B.
Chen W.
Wong MW.
Gonzalez C.
Pople JA.
Gaussian 03, Revision C.02
Gaussian
Inc.;
Wallingford (CT):
2004.
<A NAME="RA55610ST-47">47 </A>
Huenerbein R.
Schirmer B.
Moellmann J.
Grimme S.
Phys. Chem. Chem. Phys.
2010, DOI:
10.1039/C003951A.
48a </A>
Curtiss LA.
Raghavachari K.
Trucks GW.
Pople JA.
J. Chem. Phys.
1991,
94:
7221
48b </A>
Curtiss LA.
Raghavachari K.
Redfern PC.
Rassolov V.
Pople JA.
J. Chem. Phys.
1998,
109:
7764
48c </A>
Curtiss LA.
Redfern PC.
Raghavachari K.
J. Chem. Phys.
2007,
126:
084108
49a </A>
Montgomery JA.
Frisch MJ.
Ochterski JW.
Petersson GA.
J. Chem. Phys.
1999,
110:
2822
49b </A>
Montgomery JA.
Frisch MJ.
Ochterski JW.
Petersson GA.
J. Chem. Phys.
2000,
112:
6532
<A NAME="RA55610ST-50">50 </A>
Grimme S.
J.
Comput. Chem.
2003,
24:
1549
51a </A>
Hoppe D.
Angew. Chem. Int. Ed., Engl.
1997,
36:
2282
Angew. Chem.
1997,
109:
2376
51b </A>
Hoppe D.
Synthesis
2009,
43
52a </A>
Lange H.
Huenerbein R.
Wibbeling B.
Fröhlich R.
Grimme S.
Hoppe D.
Synthesis
2008,
2905
52b </A>
Lange H.
Huenerbein R.
Fröhlich R.
Grimme S.
Hoppe D.
Chem.
Asian J.
2008,
3:
78
<A NAME="RA55610ST-53">53 </A>
Komatsu K.
Murata M.
Murata Y.
Science
2005,
307:
238
54a </A>
Carravetta M.
Danquigny A.
Mamone S.
Cuda F.
Johannessen O.
Heinmaa I.
Panesar K.
Stern R.
Grossel M.
Horsewill A.
Samoson A.
Murata M.
Murata Y.
Komatsu K.
Levitt M.
Phys. Chem. Chem. Phys.
2007,
9:
4879
54b </A>
Xu M.
Sebastianelli F.
Bačić Z.
Lawler R.
Turro N.
J.
Chem. Phys.
2008,
129:
064313
54c </A>
Turro N.
Marti A.
Chen J.-C.
Jockusch S.
Lawler R.
Sartori MRE.
Chuang S.-C.
Komatsu K.
Murata Y.
J. Am. Chem. Soc.
2008,
130:
10506
54d </A>
Whitener K.
Frunzi M.
Iwamatsu S.
Murata S.
Cross R.
Saunders M.
J. Am. Chem. Soc.
2008,
130:
13996
54e </A>
Slanina Z.
Pulay P.
Nagase S.
J.
Chem. Theory Comput.
2006,
2:
782
54f </A>
Yoon M.
Yang S.
Wang E.
Zhang Z.
Nano Lett.
2007,
7:
2578
54g </A>
Darwish A.
Annu.
Rep. Prog. Chem., Sect. A
2008,
104:
360
54h </A>
Ren YX.
Ng TY.
Liew KM.
Carbon
2006,
44:
397
54i </A>
Dodziuk H.
Chem.
Phys. Lett.
2005,
410:
39
54j </A>
Barajas-Barraza R.
Guirado-López R.
Phys.
Rev. B
2002,
66:
155426
54k </A>
Türker L.
Erkoç S.
THEOCHEM
2003,
638:
37
54l </A>
Türker L.
Erkoç S.
Chem. Phys.
Lett.
2006,
426:
222
54m </A>
Yang C.-K.
Carbon
2007,
45:
2445
<A NAME="RA55610ST-55">55 </A>
Kruse H.
Grimme S.
J. Phys. Chem. C
2009,
113:
17006
