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  • 1
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    Catalytic reduction of dinitrogen to ammonia at a single molybdenum center (2003)
    American Association for the Advancement of Science (AAAS)
    Details
    Publication Date: 2003-07-05
    Description: Dinitrogen (N2) was reduced to ammonia at room temperature and 1 atmosphere with molybdenum catalysts that contain tetradentate [HIPTN3N]3- triamidoamine ligands (such as [HIPTN3N]Mo(N2), where [HIPTN3N]3- is [(3,5-(2,4,6-i-Pr3C6H2)2C6H3NCH2CH2)3N]3-) in heptane. Slow addition of the proton source [(2,6-lutidinium)(BAr'4), where Ar' is 3,5-(CF3)2C6H3]and reductant (decamethyl chromocene) was critical for achieving high efficiency ( approximately 66% in four turnovers). Numerous x-ray studies, along with isolation and characterization of six proposed intermediates in the catalytic reaction under noncatalytic conditions, suggest that N2 was reduced at a sterically protected, single molybdenum center that cycled from Mo(III) through Mo(VI) states.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Yandulov, Dmitry V -- Schrock, Richard R -- GM 31978/GM/NIGMS NIH HHS/ -- New York, N.Y. -- Science. 2003 Jul 4;301(5629):76-8.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/12843387" target="_blank"〉PubMed〈/a〉
    Keywords: Ammonia/*chemistry ; Atmospheric Pressure ; Catalysis ; Chromium/chemistry ; Electrons ; Ligands ; Magnetic Resonance Spectroscopy ; Molybdenum/*chemistry ; Nitrogen/*chemistry ; Nitrogenase/metabolism ; Organometallic Compounds/chemistry ; Oxidation-Reduction ; Protons ; Temperature
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
    Published by American Association for the Advancement of Science (AAAS)
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  • 2
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    Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis (2008)
    Nature Publishing Group (NPG)
    Details
    Publication Date: 2008-11-18
    Description: Discovery of efficient catalysts is one of the most compelling objectives of modern chemistry. Chiral catalysts are in particularly high demand, as they facilitate synthesis of enantiomerically enriched small molecules that are critical to developments in medicine, biology and materials science. Especially noteworthy are catalysts that promote-with otherwise inaccessible efficiency and selectivity levels-reactions demonstrated to be of great utility in chemical synthesis. Here we report a class of chiral catalysts that initiate alkene metathesis with very high efficiency and enantioselectivity. Such attributes arise from structural fluxionality of the chiral catalysts and the central role that enhanced electronic factors have in the catalytic cycle. The new catalysts have a stereogenic metal centre and carry only monodentate ligands; the molybdenum-based complexes are prepared stereoselectively by a ligand exchange process involving an enantiomerically pure aryloxide, a class of ligands scarcely used in enantioselective catalysis. We demonstrate the application of the new catalysts in an enantioselective synthesis of the Aspidosperma alkaloid, quebrachamine, through an alkene metathesis reaction that cannot be promoted by any of the previously reported chiral catalysts.〈br /〉〈br /〉〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2663850/" target="_blank"〉〈img src="https://static.pubmed.gov/portal/portal3rc.fcgi/4089621/img/3977009" border="0"〉〈/a〉   〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2663850/" target="_blank"〉This paper as free author manuscript - peer-reviewed and accepted for publication〈/a〉〈br /〉〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Malcolmson, Steven J -- Meek, Simon J -- Sattely, Elizabeth S -- Schrock, Richard R -- Hoveyda, Amir H -- GM-59426/GM/NIGMS NIH HHS/ -- R01 GM059426/GM/NIGMS NIH HHS/ -- R01 GM059426-09/GM/NIGMS NIH HHS/ -- England -- Nature. 2008 Dec 18;456(7224):933-7. doi: 10.1038/nature07594. Epub 2008 Nov 16.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/19011612" target="_blank"〉PubMed〈/a〉
    Keywords: Alkenes/*chemistry ; Aspidosperma/*chemistry ; Catalysis ; Indole Alkaloids/*chemical synthesis/chemistry ; Ligands ; Molecular Structure ; Molybdenum/*chemistry ; Stereoisomerism
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Published by Nature Publishing Group (NPG)
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  • 3
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    Turkey must end violent response to protests (2013)
    American Association for the Advancement of Science (AAAS)
    Details
    Publication Date: 2013-07-23
    Description: 〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Altindis, Emrah -- Alpar, M Ali -- Aksay, Emre -- Beckwith, Jonathan -- Bokel, Christian -- Curl, Robert F -- Darnell, Robert B -- Elledge, Stephen J -- Erman, Burak -- Frahm, Jens -- Goff, Stephen P -- Greengard, Paul -- Hoffmann, Roald -- Ilhan, Bayazit -- Kaslin, Jan -- Lipkin, Steven M -- Poulopoulou, Cornelia -- Raz, Erez -- Rubin, Mark A -- Salturk, Mehmet -- Schrock, Richard R -- Trautmann, Alain -- Unutmaz, Derya -- Weinstein, Harel -- Kizil, Caghan -- New York, N.Y. -- Science. 2013 Jul 19;341(6143):236. doi: 10.1126/science.341.6143.236-a.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/23869001" target="_blank"〉PubMed〈/a〉
    Keywords: Asphyxia/*chemically induced/mortality ; Hospitalization/statistics & numerical data ; *Human Rights ; Humans ; Tear Gases/*toxicity ; Turkey ; Violence/*prevention & control ; Wounds and Injuries/etiology/mortality
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 4
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    Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis (2011)
    Nature Publishing Group (NPG)
    Details
    Publication Date: 2011-11-05
    Description: Many natural products contain a C = C double bond through which various other derivatives can be prepared; the stereochemical identity of the alkene can be critical to the biological activities of such molecules. Catalytic ring-closing metathesis (RCM) is a widely used method for the synthesis of large unsaturated rings; however, cyclizations often proceed without control of alkene stereochemistry. This shortcoming is particularly costly when the cyclization reaction is performed after a long sequence of other chemical transformations. Here we outline a reliable, practical and general approach for the efficient and highly stereoselective synthesis of macrocyclic alkenes by catalytic RCM; transformations deliver up to 97% of the Z isomer owing to control induced by a tungsten-based alkylidene. Utility is demonstrated through the stereoselective preparation of epothilone C (refs 3-5) and nakadomarin A (ref. 6), the previously reported syntheses of which have been marred by late-stage, non-selective RCM. The tungsten alkylidene can be manipulated in air, delivering the products in useful yields with high stereoselectivity. As a result of efficient RCM and re-incorporation of side products into the catalytic cycle with minimal alkene isomerization, desired cyclizations proceed in preference to alternative pathways, even under relatively high substrate concentration.〈br /〉〈br /〉〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3211109/" target="_blank"〉〈img src="https://static.pubmed.gov/portal/portal3rc.fcgi/4089621/img/3977009" border="0"〉〈/a〉   〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3211109/" target="_blank"〉This paper as free author manuscript - peer-reviewed and accepted for publication〈/a〉〈br /〉〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Yu, Miao -- Wang, Chenbo -- Kyle, Andrew F -- Jakubec, Pavol -- Dixon, Darren J -- Schrock, Richard R -- Hoveyda, Amir H -- GM-59426/GM/NIGMS NIH HHS/ -- R01 GM059426/GM/NIGMS NIH HHS/ -- R01 GM059426-12/GM/NIGMS NIH HHS/ -- England -- Nature. 2011 Nov 2;479(7371):88-93. doi: 10.1038/nature10563.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/22051677" target="_blank"〉PubMed〈/a〉
    Keywords: Alkanes/chemistry ; Alkenes/chemistry ; Biological Products/*chemical synthesis/chemistry ; Carbolines/chemical synthesis/chemistry ; Catalysis ; Chemistry Techniques, Synthetic/*methods ; Cyclization ; Epothilones/chemical synthesis/chemistry ; Stereoisomerism
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
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  • 5
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    Catalytic Z-selective olefin cross-metathesis for natural product synthesis (2011)
    Nature Publishing Group (NPG)
    Details
    Publication Date: 2011-03-25
    Description: Alkenes are found in many biologically active molecules, and there are a large number of chemical transformations in which alkenes act as the reactants or products (or both) of the reaction. Many alkenes exist as either the E or the higher-energy Z stereoisomer. Catalytic procedures for the stereoselective formation of alkenes are valuable, yet methods enabling the synthesis of 1,2-disubstituted Z alkenes are scarce. Here we report catalytic Z-selective cross-metathesis reactions of terminal enol ethers, which have not been reported previously, and of allylic amides, used until now only in E-selective processes. The corresponding disubstituted alkenes are formed in up to 〉98% Z selectivity and 97% yield. These transformations, promoted by catalysts that contain the highly abundant and inexpensive metal molybdenum, are amenable to gram-scale operations. Use of reduced pressure is introduced as a simple and effective strategy for achieving high stereoselectivity. The utility of this method is demonstrated by its use in syntheses of an anti-oxidant plasmalogen phospholipid, found in electrically active tissues and implicated in Alzheimer's disease, and the potent immunostimulant KRN7000.〈br /〉〈br /〉〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3082443/" target="_blank"〉〈img src="https://static.pubmed.gov/portal/portal3rc.fcgi/4089621/img/3977009" border="0"〉〈/a〉   〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3082443/" target="_blank"〉This paper as free author manuscript - peer-reviewed and accepted for publication〈/a〉〈br /〉〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Meek, Simon J -- O'Brien, Robert V -- Llaveria, Josep -- Schrock, Richard R -- Hoveyda, Amir H -- GM-59426/GM/NIGMS NIH HHS/ -- R01 GM059426/GM/NIGMS NIH HHS/ -- R01 GM059426-12/GM/NIGMS NIH HHS/ -- England -- Nature. 2011 Mar 24;471(7339):461-6. doi: 10.1038/nature09957.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/21430774" target="_blank"〉PubMed〈/a〉
    Keywords: Adjuvants, Immunologic/chemical synthesis/chemistry ; Alkenes/*chemical synthesis/*chemistry ; Amides/chemical synthesis/chemistry ; Antioxidants/metabolism ; Biological Products/*chemical synthesis/*chemistry ; Catalysis ; Ethers/chemistry ; Galactosylceramides/chemical synthesis/chemistry ; Molecular Structure ; Molybdenum/chemistry ; Plasmalogens/chemical synthesis/chemistry ; Stereoisomerism
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
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  • 6
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    Saturation of cubic optical nonlinearity in long-chain polyene oligomers (1994)
    American Association for the Advancement of Science (AAAS)
    Details
    Publication Date: 1994-08-19
    Description: The scaling of the cubic nonlinearity gamma with chain length in polyenic molecules has received considerable theoretical attention. Earlier experimental investigations have been restricted to oligomers with fewer than 20 double bonds because of problems associated with the synthesis and solubility of conjugated molecules. These synthetic difficulties have been overcome in the present study by the use of modern living polymerization techniques. Solution measurements of gamma as a function of chain length in long-chain (up to 240 double bonds) model polyene oligomers are reported. A saturation of the increase of gamma with chain length is observed, and the onset of this saturation occurs for chain lengths considerably longer than predicted from theory.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Samuel, I D -- Ledoux, I -- Dhenaut, C -- Zyss, J -- Fox, H H -- Schrock, R R -- Silbey, R J -- New York, N.Y. -- Science. 1994 Aug 19;265(5175):1070-2.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/17832897" target="_blank"〉PubMed〈/a〉
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 7
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    Kinetically controlled E-selective catalytic olefin metathesis (2016)
    American Association for the Advancement of Science (AAAS)
    Details
    Publication Date: 2016-04-30
    Description: A major shortcoming in olefin metathesis, a chemical process that is central to research in several branches of chemistry, is the lack of efficient methods that kinetically favor E isomers in the product distribution. Here we show that kinetically E-selective cross-metathesis reactions may be designed to generate thermodynamically disfavored alkenyl chlorides and fluorides in high yield and with exceptional stereoselectivity. With 1.0 to 5.0 mole % of a molybdenum-based catalyst, which may be delivered in the form of air- and moisture-stable paraffin pellets, reactions typically proceed to completion within 4 hours at ambient temperature. Many isomerically pure E-alkenyl chlorides, applicable to catalytic cross-coupling transformations and found in biologically active entities, thus become easily and directly accessible. Similarly, E-alkenyl fluorides can be synthesized from simpler compounds or more complex molecules.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Nguyen, Thach T -- Koh, Ming Joo -- Shen, Xiao -- Romiti, Filippo -- Schrock, Richard R -- Hoveyda, Amir H -- GM-59426/GM/NIGMS NIH HHS/ -- New York, N.Y. -- Science. 2016 Apr 29;352(6285):569-75. doi: 10.1126/science.aaf4622.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA. ; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA. ; Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA. amir.hoveyda@bc.edu.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/27126041" target="_blank"〉PubMed〈/a〉
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 8
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    Catalysis by transition metals: metal-carbon double and triple bonds (1983)
    American Association for the Advancement of Science (AAAS)
    Details
    Publication Date: 1983-01-07
    Description: Several well-characterized transition metal catalysts contain a metal-carbon double bond or a metal-carbon triple bond. In other homogeneous (or heterogeneous) catalyst systems in which the metal is likely to be in a relatively high oxidation state, such as molybdenum(VI) or tungsten(VI), metal-carbon multiple bonds may play an important role. Some recent results suggest that even supposedly well understood reactions such as ethylene polymerization may actually involve catalysts that behave as if they contained a metal-carbon double bond instead of a metal-carbon single bond. The chemistry of metal-carbon double and triple bonds should eventually complement and perhaps. overlap the known chemistry of complexes containing metal-oxygen double bonds or metal-nitrogen triple bonds, respectively; unique catalytic reactions involving carbon, nitrogen, and oxygen ligands multiply bonded to transition metals are therefore possible.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Schrock, R R -- New York, N.Y. -- Science. 1983 Jan 7;219(4580):13-8.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/17734309" target="_blank"〉PubMed〈/a〉
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 9
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    Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis (2016)
    Nature Publishing Group (NPG)
    Details
    Publication Date: 2016-03-25
    Description: Olefin metathesis has had a large impact on modern organic chemistry, but important shortcomings remain: for example, the lack of efficient processes that can be used to generate acyclic alkenyl halides. Halo-substituted ruthenium carbene complexes decompose rapidly or deliver low activity and/or minimal stereoselectivity, and our understanding of the corresponding high-oxidation-state systems is limited. Here we show that previously unknown halo-substituted molybdenum alkylidene species are exceptionally reactive and are able to participate in high-yielding olefin metathesis reactions that afford acyclic 1,2-disubstituted Z-alkenyl halides. Transformations are promoted by small amounts of a catalyst that is generated in situ and used with unpurified, commercially available and easy-to-handle liquid 1,2-dihaloethene reagents, and proceed to high conversion at ambient temperature within four hours. We obtain many alkenyl chlorides, bromides and fluorides in up to 91 per cent yield and complete Z selectivity. This method can be used to synthesize biologically active compounds readily and to perform site- and stereoselective fluorination of complex organic molecules.〈br /〉〈br /〉〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4858352/" target="_blank"〉〈img src="https://static.pubmed.gov/portal/portal3rc.fcgi/4089621/img/3977009" border="0"〉〈/a〉   〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4858352/" target="_blank"〉This paper as free author manuscript - peer-reviewed and accepted for publication〈/a〉〈br /〉〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Koh, Ming Joo -- Nguyen, Thach T -- Zhang, Hanmo -- Schrock, Richard R -- Hoveyda, Amir H -- GM-57212/GM/NIGMS NIH HHS/ -- GM-59426/GM/NIGMS NIH HHS/ -- R01 GM059426/GM/NIGMS NIH HHS/ -- England -- Nature. 2016 Mar 24;531(7595):459-65. doi: 10.1038/nature17396.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA. ; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/27008965" target="_blank"〉PubMed〈/a〉
    Keywords: Alkenes/chemical synthesis/*chemistry ; Biological Products/chemical synthesis/chemistry ; Bromides/*chemical synthesis/chemistry ; Catalysis ; Chlorides/*chemical synthesis/chemistry ; Fluorides/*chemical synthesis/chemistry ; *Halogenation ; Molybdenum/chemistry
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
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  • 10
    Electronic Resource
    Electronic Resource
    Conjugation length dependence of Raman scattering in a series of linear polyenes: Implications for polyacetylene (1991)
    College Park, Md. : American Institute of Physics (AIP)
    The Journal of Chemical Physics 94 (1991), S. 4161-4170 
    Details
    ISSN: 1089-7690
    Source: AIP Digital Archive
    Topics: Physics , Chemistry and Pharmacology
    Notes: We have measured the solid state Raman scattering spectra of a homologous series of linear polyenes, with the number of alternated double bonds varying from 3 to 12. While we find a linear dependence of the Raman shifts of resonantly coupled modes with inverse conjugation length, we have also followed the suggestion of previous work in examining the inverse square product of the several Raman frequencies as a function of the logarithm of the measured energy gap of the molecule. This provides a linear relationship, as found for trans-polyacetylene, a result which is qualitatively consistent with the amplitude mode model of Horovitz and co-workers. We also find, consistent with previous work on polyacetylene, a monotonic decrease in the ratios of oscillator strengths of the two strongest bands with conjugation length, as recently predicted by a series of molecular dynamics calculations. Suggested interpretations of a number of qualitative observations, including splitting of modes for shorter conjugation length, are offered, and the implications for the structure of trans-polyacetylene are discussed. The present work confirms that the previously measured dispersion in the Raman spectra of trans-polyacetylene is due to a distribution of conjugation lengths and brings into question some of the quantitative aspects of the amplitude mode model.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1063/1.460649
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