Lecture Course "Physical Organic Chemistry"
Course No. 21 221a/b - Modulbeschreibung (Deutsch)
Because of the Corona-related regulations, lecture course and seminar will be provided online. Please register in Campus Management with a valid email address so that we can provide you with detailed information. For the seminar, please choose a topic for your seminar talk. Follow the quicklink "Seminar Topics" below. You will find brief information on the different topics and a Google Spreadsheet link. Please insert your name and matriculation number in the Spreadsheet.
Quicklinks:
Lecture Course Contents - Seminar Topics - Seminar schedule - Quickies - Old Exams
Addressees
Chemistry master students interested in physical organic and supramolecular chemistry. The course language will be German, if no foreign student is participating. If desired, we can switch to English.
Dates and Locations
Lecture Course: Thursdays 12 am - 2 pm; start date: Apr 23, 2020; WebEx video conference
Seminar: Thursdays 2 pm- 4 pm; start date: Apr 23, 2020; WebEx video conference
To participate as efficiently as possible, make sure that you have sufficient internet bandwith, a headset with microphone and a suitable computer/laptop available. I will send the invitations to join the video conferences to all participants.
Because of a Berlin-wide holiday, there will be no course/seminar on May 21, 2020
Organizational Matters
Registration: Please do not forget to register for the course in Campus Management. In addition, you also need to choose a seminar topic from the list which will be made available in front of my office (room 32.05) after the first lecture course date. Please sign up for the desired topic with name and matriculation number. If you want to step back from the course, you must do that before the registration deadline. After this date, registration is fixed.
Attendance: It is completely up to you to attend the lecture course. If you feel that you can learn the topics of the course better on your own, please feel free to use the time in any way beneficial to you. However, I expect that all participants attend the seminar. It is not quite fair, if you only show up for your own talk. Your fellow students tend to put quite some effort into their talks and constantly not being in the audience is - at least in my opinion - a sign of disrespect. Anyway, at the end you need to be fit for the exam.
Seminar: The seminar will expand the topics of the lecture course in seminar talks given by the participating students. The seminar topics provide additional examples for the concepts discussed in the lecture course. The list of topics is available on a second page. After the talks, I will make the pdfs of the presentations available by linking them to the headlines in the list of topics on the seminar page (password protected, of course). Please send me your presentations as a pdf by email after your talk.
Seminar Dates: When you choose your seminar topic, please make sure that you are available at the date of your talk. The lecture course, seminar, and excercises are scheduled to fit together as much as possible.
Materials: I will use the chalkboard for most of the lecture course, except if I need more complex transparencies, which are then available for download below. I will make them accessible to all participants
Excercises (Quickies): Two of the Quickies below will be discussed in the beginning of each lecture course/seminar day. Please download and prepare them.
Active participation: To pass the course and finish the module, active participation is one requirement, to pass the oral exam is the second one. Active participation means that you give a seminar talk AND participate in the discussion of the quickies.
Exam: The course is completed by an oral exam of ca. 30 minutes which comprises the topics of the lecture course as well as the topics of the seminar. The grade of the oral exam defines the grade for the module. The exam can be individually scheduled with me, but is to be taken before the start of the next term.
Old Exams
Earlier, the exam has been a written exam. You find the exams here for training purposes. You need to login with the same password as for the other material associated to this lecture course to access both.
Summer term 2008:
PDF of Exam (English) - PDF of Exam (German)
Summer term 2009:
PDF of Exam (English) - PDF of Exam (German)
Summer term 2011:
PDF of Exam (English) - PDF of Exam with Solutions
Lecture Course Contents
Chapter 1 - Fundamentals
1.1 Potential Energy Surfaces
identity reaction of H + H2 to H2 + H , discussion of the connection of potential energy surfaces to vibrations, to the reaction path, to the imaginary frequency in quantum chemical calculations etc. How many dimensions does a PES have? What exactly is a reaction coordinate?
1.2 Thermodynamics
energy units, factors that affect entropy, connection of free enthalpies and equilibria, connection to potential energy surfaces
1.3 Kinetics
simple rate laws for unimolecular and bimolecular reactions, Arrhenius equation, Eyring equation, transition state theory, kinetic vs. thermodynamic control, pressure effects (activation volumes and their meaning), catalysis, enzyme kinetics (Michaelis-Menten)
1.4 Linking Kinetics to Thermodynamics
Hammond postulate, Curtin-Hammett principle, linear-free enthalpy correlations (Hammett equation, the meaning of sigma and rho, substituent effects, direct conjugation)
1.5 Investigation of Reaction Mechanisms and Short-Lived Intermediates
kinetic isotope effects, crossover experiments (reaction trajectories; example: Eschenmoser's intra- versus intermolecular SN2 reaction), characterization of short-lived intermediates by three-phase test, matrix-isolation spectroscopy etc., examples for reactive species (dioxiranes, tetrahedrane, o,m,p-didehydrobenzene (including the Bergman cyclization), water oxide)
1.6 Short Summary of Stereochemistry
euclidean and topological chirality, central, axial, helical, planar chirality, chirality and symmetry
Chapter 2 - Structure and Bonding
2.1 Molecular Orbital Theory
how to qualitatively construct molecular-orbitals (knot rule etc.), frontier orbitals and why one often can restrict the discussion to the FOs, molecular orbital basis for HSAB principle, nucleophilicity, electrophilicity
Materials II: MO scheme of methane without hybridized carbon
2.2 Aromaticity
Hückel theory (qualitatively), molecular orbital schemes of cyclobutadiene, benzene and cyclooctatetraene, Jahn-Teller theorem, aromaticity - nonaromaticity - antiaromaticity, homoaromaticity, in plane aromaticity, through-space aromaticity, fullerenes
2.3 Conformational Analysis (strain, alicyclics, cyclics, stereoelectronic effects)
strain, stereoelectronic effects
Chapter 3 - Reactivity
3.1 Classification of Reaction Types
polar reactions (nucleophiles, electrophiles), radical reactions, photochemical reactions, pericyclic reactions (this part is meant to provide a brief overview as an introduction mainly into pericyclic reactions)
3.2 Classification of Pericyclic Reactions and Woodward-Hoffman Rules
cycloadditions (allowed - forbidden), electrocyclic reactions (conrotatory - disrotatory), sigmatropic rearrangements (suprafacial - antarafacial), cheletropic reactions (side-on - end-on), aromatic transition structures
3.3 Cycloaddition and Cycloreversion Reactions
introduction to correlation diagrams (1 example for [4+2], 1 example for [2+2]) for deriving the Woodward-Hoffman rules from a molecular orbital approach, comparison to FO method, examples (Diels-Alder, exo/endo, 1,3-dipolar cycloadditions)
3.4 Electrocyclic Reactions
correlation diagrams (1 example for con-, 1 example for disrotatory reaction), comparison to FO method, examples
3.5 Sigmatropic Rearrangements
FO analysis in a simple and qualitative way, examples (e.g. vitamin D, bullvalene)
3.6 Cheletropic Reactions
FO analysis, examples (e.g. carbene addition to double bonds, loss of SO2 from cyc-CH2CH=CHCH2SO2 or benzoid analoga thereof)
3.7 Group Transfer Reactions
transfer hydrogenations, ene-reaction (e.g. with singlet oxygen)
3.8 Orbital Coefficient Controlled Regioselectivity in Cycloadditions
3.9 Orbital Energy Controlled Reaction Rates of Cycloadditions
Diels-Alder with normal and inverse electron demand
3.10 Carbenes/Carbenoids, Nitrenes/Nitrenoids, and Oxenoids
generation, rearrangements, insertion, and addition
3.11 Radicals
ESR and CIDNP, rearrangements and bimolecular reactions
3.12 Photochemistry
excited states, Jablonski term scheme, energy transfer, photoinduced electron transfer, synthetically useful photochemical reactions
Chapter 4 - The Influence of the Environment
4.1 Solvatochromic Behaviour
4.2 Gas-Phase Acidities and Gas-Phase Nucleophilicities
inductive effects of alkyl chains: fact or fiction?, why is the SN2 reaction up to 10 to the power of 15 times faster in the gas phase (double minimum potential, what is a "negative barrier"?)?
Materials IV: Gas-Phase Acidities - An Absolute Acidity Scale
Materials V: Gas-Phase Nucloephilic Substitutions
Materials VI: Alkali ion/crown ether binding - is there a best fit in the gas phase?
Chapter 5 - Non-Covalent Interactions
5.1 Classification
Charge-charge attraction/repulsion, charge-dipole, dipole-dipole interactions, hydrogen bonds, pi-stacking, C-H-pi, cation-pi interactions, pi-donor-pi-acceptor interactions, Van-der-Waals forces, hydrophobic effect
Materials VII: The Properties of Non-Covalent Bonds - Some Tables
5.2 Basic Principles in Supramolecular Chemistry
lock-and-key principle, induced fit, preorganisation, self-assembly versus self-organization, template effects, cooperativity, multivalency
5.3 Host-Guest Chemistry
Methods for the investigation of dynamically bound species, one example: coffein receptor and its examination by NMR, IR, UV/VIS spectroscopies, mass spectrometry and crystallography
5.4 Examples for Architectures based on Non-Covalent Bonds
self-assembled metallo-supramolecular systems (helicates, grids, capsules), hydrogen bonded capsules, mechanically locked molecules
Materials XI: Molecular Tennis: Self-Assembling Capsules
Materials XII: Mesoscale Self-Assembly
Self-assembly and self-organization belong to the area of "emergent properties", i.e. a small set of well-defined rules plus simple building blocks make much more complex patterns evolve which are often almost unpredictable. New properties emerge which none of the building blocks have. For a very simple implementation with intriguing consequences, take a look at Conway's Game of Life (also see the related Wikipedia pages)
Materials XIII: Emergent Properties - Conway's Game of Life (Golly Win)
5.5 Implementing Function in Non-Covalently Bound Complexes
molecular devices, logic gates, molecular motors
Materials XIV: Natural molecular motors
For links to the animations used in the talk, which do not work in the pdf version, see:
Quickies
The Quickies are short excercises to be discussed in the first few minutes of each lecture course or seminar.
Quickie No. 1: | A true story: Riddles in Synthetic Chemistry |
Quickie No. 2: | Scope and limitations of the Hammond postulate Literature: H. Mayr, A.R. Ofial, Angew. Chem. 2006, 118, 1876; Angew. Chem. Int. Ed. 2006, 45, 1876 |
Quickie No. 3: | Linear Free Enthalpy Relationships - Hammett equation Solution transparency: Hammett plot |
Quickie No. 4: | Isotopic labeling, reaction trajectories, Baldwin rules Solution transparency: Baldwin rules Literature: A. Eschenmoser et al., Helv. Chim. Acta 1970, 53, 2059 |
Quickie No. 5: | Tröger's base and chirality Solution transparencies Literature: F. Vögtle, V. Schurig et al., Chem. Eur. J. 2002, 8, 3629 |
Quickie No. 6: |
Racemization kinetics of biaryl compounds |
Quickie No. 7: | To hybridize or not to hybridize: Ethane Solution transparency Literature: I. Fleming, Grenzorbitale und Reaktionen organischer Verbindungen, Wiley-VCH, Weinheim 1990 |
Quickie No. 8: | The rotational barrier of ethane Literature: P.R. Schreiner, Angew. Chem. 2002, 114, 3729; Angew. Chem. Int. Ed. 2002, 41, 3579 |
Quickie No. 9: | Cyclooctatetraene and its Dianion - Aromaticity Solution transparency Literature: F.-G. Klärner, Angew. Chem. 2001, 113, 4099; Angew. Chem. Int. Ed. 2001, 40, 3977 |
Quickie No. 10: | Aromaticity and NMR; aromaticity of fullerene |
Quickie No. 11: | Correlation diagrams: Cycloadditions and electrocyclic reactions Literature on theoretical calculations on TS of pericyclic reactions: K.N. Houk, Y. Li, J.D. Evanseck, Angew. Chem. 1992, 104, 711; Angew. Chem. Int. Ed. 1992, 31, 682 |
Quickie No. 12: | Healthy baby buttocks, skin cancer & Woodward-Hoffmann rules! Literature on light-induced DNA damage: J. Cadet, T. Douki, J.-P. Pouget, J.-L. Ravanat, UVB and UVA induced formation of photoproducts within cellular DNA, in: E. Sage, R. Drouin, M. Rouabhia (eds.), From DNA Photolesions to Mutations, Skin Cander and Cell Death, Royal Society of Chemistry, London 2005 |
Quickie No. 13: | Secondary orbital interactions |
Quickie No. 14: | Woodward-Hoffman rules, rate constants and product selectivities |
Quickie No. 15: | Cope rearrangements in bullvalene |
Quickie No. 16: | Matrix isolation spectroscopy - Carbenes Raisin bread analogy of matrix isolation spectroscopy Literature: see literature references accompanying the seminar talk on matrix isolation spectroscopy above |
Quickie No. 17: | A photochemical sensor for transition metal ions Literature: R. Krauss, U. Koert, Synlett 2003, 598 |
Quickie No. 18: | Host-guest complexes of cyclodextrins |
Quickie No. 19: | Secondary interactions in multiply hydrogen-bonded complexes Solution transparency Literature: W.L. Jorgensen, J. Pranata, J. Am. Chem. Soc. 1990, 112, 2008 T.J. Murray, S.C. Zimmerman, J. Am. Chem. Soc. 1992, 114, 4010 |
Quickie No. 20: | Design of an artificial adrenaline receptor Solution transparency Literature: M. Herm, O. Molt, T. Schrader, Chem. Eur. J. 2002, 8, 1485 |
Quickie No. 21: | Guest encapsulation in Rebek softballs Literature: J. Kang, J. Rebek, Jr., Nature 1996, 382, 239 S. Mecozzi, J. Rebek, Jr., Chem. Eur. J. 1998, 4, 1016 |
Quickie No. 22: | Rotaxane synthesis and examination of dynamic properties Literature: P. Ghosh, G. Federwisch, M. Kogej, C. A. Schalley, D. Haase, W. Saak, A. Lützen, R. Gschwind Org. Biomol. Chem. 2005, 3, 2691 |
Quickie No. 23: | Self-assembly of complex architectures from simple building blocks Solution transparency Literature: K.S. Chichak, S.J. Cantrill, A.R. Pease, S.H. Chiu, G.W.V. Cavem J.L. Atwood, J.F. Stoddart, Science 2004, 304, 1308 |
Quickie No. 24: | Hierarchical self-assembly of helicates Solution transparency Literature: M. Albrecht, S. Mirtschin, M. de Groot, I. Janser, J. Runsink, G. Raabe, M. Kogej, C.A. Schalley, R. Fröhlich, J. Am. Chem. Soc. 2005, 127, 17672 |
Further reading
Besides the references given under each seminar topic, the following literature references extend the scope of the lecture course and provide some more examples which cannot all be discussed. They provide access to more in-depth information and recent applications of the topics presented in the course. Please also see the literature references provided on the seminar page.
1. Textbooks
Physical Organic Chemistry:Supramolecular Chemistry:
- N. Isaacs, Physical Organic Chemistry, Longman, Harlow 1995
- J.W. Steed, J.L. Atwood, Supramolecular Chemistry, Wiley, New York 2000
- C.A. Schalley (ed.), Analytical Methods in Supramolecular Chemistry, Wiley-VCH, Weinheim, 2007
- G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, Oxford 1997
2. Thermodynamics and Kinetics
Catalysis within molecular capsulesHammett equation
- J. Kang, J. Santamaria, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 7389
- J. Kang, G. Hilmersson, J. Santamaria, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 3650
- T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Nature 1998, 394, 764
- S. K. Körner, F. C. Tucci, D. M. Rudkevich, T. Heinz, J. Rebek, Jr., Chem. Eur. J. 2000, 6, 187
Steric isotope effects
- P. Sykes, Reaktionsmechanismen der Organischen Chemie, Wiley-VCH, Weinheim
- D. Wade, Chem.-Biol. Interact. 1999, 117, 191
- H. C. Brown, G. J. McDonald, J. Am. Chem. Soc. 1966, 88, 2514
- S. A. Sherrod, R. L. da Costa, R. A. Barnes, V. Boekelheide, J. Am. Chem. Soc. 1974, 96, 1565
- K. Mislow, R., Graewe, A. J. Gordon, G. H. Wahl, Jr., J. Am. Chem. Soc. 1964, 86, 1733
- L. Melander, R. E. Carter, J. Am. Chem. Soc. 1964, 86, 295
- D. Wade, Chem.-Biol. Interact. 1999, 117, 191
- T. Felder, C. A. Schalley, Angew. Chem. 2003, 115, 2360
3. Reactive Intermediates
Three-phase testMatrix isolation spectroscopy (examples for reactive intermediates)
- J. Rebek, F. Gaviña, J. Am. Chem. Soc. 1974, 96, 7112
- J. Rebek, D. Brown, S. Zimmerman, J. Am. Chem. Soc. 1975, 97, 454
- J. Rebek, F. Gaviña, J. Am. Chem. Soc. 1975, 97, 3221
Neutralisation reionisation mass spectrometry (NRMS)
- G. Maier, H. P. Reisenauer, H. Pacl, Angew. Chem. 1994, 106, 1347 (silacyclopropyne)
- W. Sander, Angew. Chem. 1994, 106, 1522 (triple bonds in small cycles)
- G. Maier, Angew. Chem. 1988, 100, 317 (tetrahedrane)
- G. Maier, H. P. Reisenauer, T. Sayrac, Chem. Ber. 1982, 115, 2192
- G. Hornung, C.A. Schalley, M. Dieterle, D. Schröder, H. Schwarz, Chem. Eur. J. 1997, 3, 1866 (Barton reaction of alkoxy radikals)
4. Aromaticity - Non-Aromaticity - Antiaromaticity
ReviewsResonance energies
- P. Garratt, P. Vollhard, Aromatizität , Thieme, Stuttgart 1973 (excellent small book providing a great overview)
- P.v.R. Schleyer, H. Jiao, Pure Appl. Chem. 1996, 68, 209
- Sonderheft der Chemical Reviews: Chem. Rev. 2001, 101 (very extensive!)
Nucleus-independent chemical shifts (NICS)
- M.J.S. Dewar, C. de Llano, J. Am. Chem. Soc. 1969, 91, 789
- L.J. Schaad, B.A. Hess, Jr., Chem. Rev. 2001, 101, 1465
Aromaticity of Fullerenes
- P.v.R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N.J.R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6317
Homoaromaticity
- M. Bühl, W. Thiel, H. Jiao, P.v.R. Schleyer, M. Saunders, F.A.L. Anet, J. Am. Chem. Soc. 1994, 116, 6005
- M. Bühl, A. Hirsch, Chem. Rev. 2001, 101, 1153
Sigma-aromaticity
- R.V. Williams, Chem. Rev. 2001, 101, 1185
3D aromaticity
- D. Moran, M. Manoharan, T. Heine, P.v.R. Schleyer, Org. Lett. 2003, 5, 23
- M.J.S. Dewar, J. Am. Chem. Soc. 1984, 106, 669
- D. Cremer, J. Gauss, J. Am. Chem. Soc. 1986, 108, 7467
Antiaromaticity
- M. Bremer, P.v.R. Schleyer, K. Schötz, M. Kausch, M. Schindler, Angew. Chem. 1987, 99, 795
- M.S.W. Chan, D.R. Arnold, Can. J. Chem. 1997, 75, 192
Historical perspective on the development of the term "aromaticity"
- F.-G. Klärner, Angew. Chem. 2001, 113, 4099
- K.B. Wiberg, Chem. Rev. 2001, 101, 1317
- P. Garratt, Endeavour 1987, 11, 36
- J.A. Berson, Angew. Chem. 1996, 108, 2922
5. Pericyclic Reactions
Basics (in german, but they are also available in english)Aromaticity and pericyclic reactions
- Ian Fleming, Grenzorbitale und Reaktionen organischer Verbindungen, VCH, Weinheim 1990
- R.B. Woodward, R. Hoffmann, Die Erhaltung der Orbitalsymmetrie, VCH, Weinheim 1970
Transition structures (theoretical calculations)
- M.J.S. Dewar, Angew. Chem. 1971, 83, 859
- K.-W. Shen, J. Chem. Educ. 1973, 50, 238
Pericyclic reactions in organic synthesis:
- K.N. Houk, Y. Li, J.D. Evanseck, Angew. Chem. 1992, 104, 711
- F. Bernardi, M. Olivucci, M.A. Robb, Acc. Chem. Res. 1990, 23, 405
- B.M. Trost, Angew. Chem. 1986, 98, 1
- J. Mulzer, Nachr. Chem. Tech. Lab. 1984, 32, 882 + 961
- A. Ichihara, Synthesis 1987, 207
- W. Oppolzer, Angew. Chem. 1977, 89, 10
- S. Blechert, Synthesis 1989, 71
6. Two-state Reactivity
ReviewsOriginal literature
- D. Griller, K.U. Ingold, Acc. Chem. Res. 1980, 13, 317 (radical clocks)
- P.R. Ortiz de Montellano, J.J. De Voss, Nat. Prod. Rep. 2002, 19, 477 (cytochrome P-450)
- J.T. Groves, G.A. McClusky, R.E. White, M.J. Coon, Biochem. Biophys. Res. Commun. 1978, 81, 154 (oxygen rebound mechanism)
- J.I. Manchester, J.P. Dinnocenzo, L.-A. Higgins, J.P. Jones, J. Am. Chem. Soc. 1997, 119, 5069 (isotope effect profiles)
- M. Newcomb, M.-H. Le Tadic, D.A. Putt, P.F. Hollenberg, J. Am. Chem. Soc. 1995, 117, 3312 (ultrafast radical clocks)
- M. Newcomb, M.-H. Le Tadic-Biadatti, D.L. Chestney, E.S. Roberts, P.F. Hollenberg, J. Am. Chem. Soc. 1995, 117, 12085
7. Photochemistry and Artificial Photosynthesis
BooksArtificial photosynthesis
- H.G.O. Becker, Einführung in die Photochemie , Akademie Verlag
- C.H. DePuy, O.L. Chapman, Molekül-Reaktionen und Photochemie, VCH, Weinheim 1977
- M. Klessinger, J. Michl, Excited States and Photochemistry of Organic Molecules, Wiley-VCH, Weinheim 1995
- V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines, Wiley-VCH, Weinheim 2003
- G. Steinberg-Yfrach, P.A. Liddell, S.-C. Hung, A.L. Moore, D. Gust, T.A. Moore, Nature 1997, 385, 239
- Y.-Z. Hu, S. H. Bossmann, D. van Loyen, O. Schwarz, H. Dürr, Chem. Eur. J. 1999, 5, 1267
8. Solvent Effects
Solvatochromic behaviourGas-phase acidities, gas-phase nucleophilicities
- Lowry, Richardson, Mechanismus und Theorie in der Organischen Chemie, VCH, Weinheim
- Reichard, Dimroth, Angew. Chem. 1979, 91, 119
- F. Strohbusch, Chem. unserer Zeit 1982, 16, 103
- W.N. Olmstead, J.I. Brauman, J. Am. Chem. Soc. 1977, 99, 4219
- M.J. Pellerite, J.I. Brauman, J. Am. Chem. Soc. 1980, 102, 5993
9. Non-covalent Bonds, Supramolecular Chemistry
Individual non-covalent interactionsDetermination of binding constants
- R. D. Hancock, J. Chem. Ed. 1992, 69, 615 (chelate effect)
- W.L. Jorgensen, J. Pranata, J. Am. Chem. Soc. 1990, 112, 2008 (secondary effects)
- T.J. Murray, S.C. Zimmerman, J. Am. Chem. Soc. 1992, 114, 4010 (secondary effects)
- J.C. Ma, D.A. Dougherty, Chem. Rev. 1997, 97, 1303 (cation-pi interaction)
- C.A. Hunter, J.K.M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525 (pi-pi interaction)
- D.B. Smithrud et al., Pure Appl. Chem. 1990, 62, 2227 (solvent effects, hydrophobic effect)
Preorganization
- K. A. Connors, Binding Constants , Wiley, New York 1987
- S.R. Waldvogel, R. Fröhlich, C.A. Schalley, Angew. Chem. 2000, 112, 2580 (caffeine receptor)
Allosteric behaviour
- D.J. Cram, Angew. Chem. 1988, 100, 1041 (Nobel lecture)
- J. Rebek, Jr. et al., J. Am. Chem. Soc. 2001, 123, 11519 ("flexiballs")
- A. Lützen, O. Haß. T. Bruhn, Tetrahedron Lett. 2002, 43, 1807
10. Molecular Devices
Natural molecular motorsArtificial molecular "motors"
- Biochemistry textbooks(z.B. Voet, Voet)
- P. D. Boyer, Angew. Chem. 1998, 110, 2424
- J. E. Walker, Angew. Chem. 1998, 110, 2438
- C. A. Schalley, K. Beizai, F. Vögtle, Acc. Chem. Res. 2001, 34, 465
- J.-P. Collin, C. Dietrich-Buchecker, P. Gaviña, M. C. Jimenez-Molero, J.-P. Sauvage, Acc. Chem. Res. 2001, 34, 477
- V. Balzani, M. Gómez-López, J. F. Stoddart, Acc. Chem. Res. 1998, 31, 405
- A. M. Brouwer, C. Frochot, F. G. Gatti, D. A. Leigh, L. Mottier, F. Paolucci, S. Roffia, G. W. H. Wurpel, Science 2001, 291, 2124
- P. R. Ashton, V. Balzani, O. Kocian, L. Prodi, N. Spencer, J. F. Stoddart, J. Am. Chem. Soc. 1998, 120, 11190
- J. K. Gimzewski, C. Joachim, R. R. Schlittler, V. Langlais, H. Tang, I. Johannsen, Science 1998, 281, 531
- T. R. Kelly et al., Nature 1999, 401, 150
- B. L. Feringa et al., Nature 1999, 401, 152